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The Purple Gang: Detroit's Mafia and the Bloodiest Battle for Prohibition's Deadliest River (True Crime History for Sleep) · Sleepless History: Sleep Documentaries

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[SPEAKER_00]: Hello and welcome back to Sleepless History.
0:03
[SPEAKER_00]: I'm glad you're here.
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[SPEAKER_00]: Tonight's story takes us to a place that might surprise you.
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[SPEAKER_00]: If you've only ever thought of 1920s gangland violence, as a Chicago story.
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[SPEAKER_00]: or a New York story.
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[SPEAKER_00]: Tonight we're going to Detroit, Michigan, a city of factories and furnaces and immigrant neighborhoods sitting directly across a narrow cold river from Canada.
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[SPEAKER_00]: We're going to talk about a stretch of water barely half a mile wide at its narrowest point.
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[SPEAKER_00]: A stretch of water that, for 13 long years, carried more illegal liquor into the United States than any other single crossing in the entire country.
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[SPEAKER_00]: Some historians place the estimate as high as 75% of all smuggled alcohol entering America during prohibition.
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[SPEAKER_00]: Three out of every four bottles.
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[SPEAKER_00]: through one narrow channel between two cities that most people even now don't associate with organised crime at all and we're going to talk about the people who ran that channel.
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[SPEAKER_00]: not the Italian-American crime families that so much of our popular imagination has settled on when we picture the prohibition era.
1:24
[SPEAKER_00]: Tonight's story belongs to a different group entirely.
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[SPEAKER_00]: A syndicate of young Jewish American men, many of them still in their teens and early twenties when it began.
1:37
[SPEAKER_00]: the American born sons of immigrants who had fled the pogroms and poverty of the old Russian empire, looking for something better on Detroit's lower east side.
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[SPEAKER_00]: They called themselves at various points, the sugar house boys, and later more famously the purple gang.
1:56
[SPEAKER_00]: And by the height of their power in the late 1920s, they controlled not just the liquor trade,
2:07
[SPEAKER_00]: and a private, semi-legal army of hijackers and gunmen, so feared that even Al Capone, a man who did not scare easily, chose to make peace with them rather than fight them for territory.
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[SPEAKER_00]: This is a long story, with a lot of names in it, and a lot of dates, and a fair amount of violence, because that is simply what this history contains.
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[SPEAKER_00]: I won't dwell on the gore.
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[SPEAKER_00]: that isn't what this show is for.
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[SPEAKER_00]: But I will tell you the story honestly, the way it happened, slowly and thoroughly.
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[SPEAKER_00]: If your mind starts to wander partway through, that's perfectly fine.
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[SPEAKER_00]: Before we begin, if you're finding this show useful for settling your mind down at the end of the day,
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[SPEAKER_00]: Lastly, before we begin tonight's story, a quick note, sleepless history is independent, no network behind it, just careful research and quiet evenings.
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[SPEAKER_00]: If these stories have become part of your nightly routine, you can support the show on Patreon
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[SPEAKER_00]: linked in the show notes.
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[SPEAKER_00]: There you will find episodes with ad-free listening, episodes with different or no background audio, plus early access to future episodes.
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[SPEAKER_00]: And if that's not for you right now, that's okay.
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[SPEAKER_00]: Simply commenting or following the show helps adjust as much.
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[SPEAKER_00]: now get comfortable and let's drift back together about a hundred years to a narrow street on the east side of Detroit, Michigan where this story really begins.
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[SPEAKER_00]: Chapter 1 Little Jerusalem and the Sugar House Boys To understand the purple gang you first have to understand the neighbourhood that made them.
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[SPEAKER_00]: And to understand the neighborhood, you have to go back even further to the closing decades of the 1800s.
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[SPEAKER_00]: When a great wave of Jewish immigration began pouring out of the Russian Empire and into the United States.
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[SPEAKER_00]: These were families fleeing organized violence, fleeing legal restrictions on where they could live and what work they could do.
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[SPEAKER_00]: Fleeing a world that had made very clear, it did not want them.
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[SPEAKER_00]: Between roughly 1881 and 1914.
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[SPEAKER_00]: millions of Jewish immigrants crossed the Atlantic Ocean, and while many settled in the tenements of New York City, a significant number will keep moving west, following the promise of industrial jobs, and one of the cities they landed in, in growing numbers, was Detroit.
5:16
[SPEAKER_00]: At the turn of the century Detroit was becoming one of America's great industrial boom towns.
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[SPEAKER_00]: This was, after all, the birthplace of the modern automobile industry.
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[SPEAKER_00]: Henry Ford's factories were hungry for labor, and the city's population was swelling with newcomers of every background, drawn by the promise of steady wages.
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[SPEAKER_00]: Amid this growth, a Jewish immigrant community took root on Detroit's Lower East Side.
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[SPEAKER_00]: In a neighborhood bounded roughly by Grasher Avenue, brush street, Willis Avenue, and Russell Street.
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[SPEAKER_00]: The residents themselves, affectionately, and sometimes not so affectionately, called it Little Jerusalem.
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[SPEAKER_00]: It was a crowded, close-knit world of small shops, kosher butchers, synagogues, and tenement housing, not unlike similar immigrant enclaves in other American cities, full of families working hard to build a foothold
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[SPEAKER_00]: were the Bernstein's.
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[SPEAKER_00]: The Bernstein family had emigrated from the Russian Empire and settled first in New York City, before moving to Detroit while their children were still young.
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[SPEAKER_00]: There were four Bernstein brothers who would become central to this story.
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[SPEAKER_00]: Abraham, known as Abe,
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[SPEAKER_00]: the eldest and the group's eventual chief strategist, Raymond, known as Ray, Joseph, sometimes called Joe, or in some accounts, given the nickname Bill Bugs, and Isodor, known as Izzy, the youngest.
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[SPEAKER_00]: Sources differ slightly on their exact birth years.
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[SPEAKER_00]: but Abe is generally believed to have been born around 1892, which would have made him a young man, not yet 30, by the time prohibition began.
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[SPEAKER_00]: Like so many other children of immigrant families crowded into a poor urban neighborhood.
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[SPEAKER_00]: The Bernstein boys did not exactly have an easy start.
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[SPEAKER_00]: They enrolled at a local institution called Bishop School, and according to several historical accounts, teachers placed them in the school's division for what were at the time.
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[SPEAKER_00]: You've domestically called problem children.
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[SPEAKER_00]: This wasn't a unique story, poverty, language barriers, overcrowded classrooms, and the simple restlessness of adolescence produced plenty of so-called problem children in immigrant neighborhoods across urban America in this period.
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[SPEAKER_00]: What made the Bernstein brothers different was who they met while sitting in that
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[SPEAKER_00]: At Bishop's School and in the surrounding streets of Little Jerusalem, the Bernstein brothers crossed paths with a cluster of other young men whose names would, in time, become notorious across Detroit and far beyond it.
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[SPEAKER_00]: There were the key well brothers, Harry and Phil.
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[SPEAKER_00]: There were the Flisha brothers, sometimes spelled Flisha, three of them.
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[SPEAKER_00]: Harry, Sam and Louie.
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[SPEAKER_00]: There was Irving Milberg, there was Irving Shapiro.
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[SPEAKER_00]: Over the following pages of this story, you'll hear these names again and again.
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[SPEAKER_00]: So it's worth letting them settle in now in earlier chapter of their lives.
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[SPEAKER_00]: Back when they were still just neighborhood boys getting into the ordinary, low grade trouble that neighborhood boys get into.
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[SPEAKER_00]: And in the
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[SPEAKER_00]: small-time mischief.
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[SPEAKER_00]: The kind of thing that happens in poor immigrant neighbourhoods in every American city in every era, shoplifting from local merchants, stealing fruit and candy from pushcarts and shopkeepers, the small extortions of childhood turning gradually into slightly larger ones,
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[SPEAKER_00]: They began robbing drunks on the street.
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[SPEAKER_00]: They began shaking down local Jewish shopkeepers, some of whom ironically were their own neighbours for small sums of protection money.
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[SPEAKER_00]: None of this, on its own, was especially remarkable.
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[SPEAKER_00]: Petty juvenile crime was common in crowded immigrant districts throughout industrial America.
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[SPEAKER_00]: What made this particular group of boys different was the direction they were about to take and the men who would help point them in it.
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[SPEAKER_00]: Sometime in the early 1920s.
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[SPEAKER_00]: or by some accounts even a bit earlier, this loose cluster of neighborhood boys came under the informal tutelage of two older, more established Detroit criminals, men named Charles Leiter and Henry Schultz.
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[SPEAKER_00]: lighter and sure operated what was on its surface, a legitimate business, a corn sugar outlet on Oakland Avenue, known locally as the Oakland Sugar House.
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[SPEAKER_00]: Corn sugar of course happened to be one of the essential raw ingredients for illegal home distilling and lighter and sure supposedly legitimate storefront was, in reality,
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[SPEAKER_00]: Functioning as a supply hub for the alley brewers and small scale bootleggers, who were beginning to multiply across the city, even before national prohibition officially began.
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[SPEAKER_00]: Lighter and shore took a liking to this cluster of tough, hungry young men from Little Jerusalem, and began using them for strong arm work, collecting debts, intimidating rivals,
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[SPEAKER_00]: The young men, in turn, began calling themselves the Sugar House Boys, or the Sugar House Gang, a name borrowed directly from their mentor's storefront on Oakland Avenue.
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[SPEAKER_00]: It's worth pausing here to notice something important about this stage of the story.
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[SPEAKER_00]: This wasn't yet a criminal empire.
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[SPEAKER_00]: It was a loose, informal confederation.
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[SPEAKER_00]: A collection of independent young operators who happen to share a neighbourhood, a set of mentors, and an increasingly violent set of habits.
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[SPEAKER_00]: That loosens that lack of any single formal chain of command would remain a defining feature of this organisation for its entire existence.
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[SPEAKER_00]: And it would eventually prove to be one of the central reasons for its downfall.
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[SPEAKER_00]: but that's a part of the story for much later.
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[SPEAKER_00]: Now, it's worth explaining briefly why any of this was happening in Detroit before national prohibition had even technically begun.
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[SPEAKER_00]: The State of Michigan actually enacted its own statewide prohibition law in 1918, a full two years ahead of the rest of the country.
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[SPEAKER_00]: When the 18th Amendment and the Volstead Act took national effect in 1920,
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[SPEAKER_00]: Those two extra years gave Michigan's bootleggers, smugglers, and organized criminals a substantial head start.
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[SPEAKER_00]: Time to build supply routes, establish smuggling techniques, and develop relationships across the Canadian border.
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[SPEAKER_00]: All before federal prohibition agents even had a national law to enforce.
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[SPEAKER_00]: By the time the rest of the United States went dry, Detroit's underworld had already been operating in the liquor train for two full years.
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[SPEAKER_00]: It was, in a real sense, ahead of the curve on an entire criminal industry.
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[SPEAKER_00]: And so it was against this backdrop, this neighborhood of striving immigrant families, this pair of underworld mentors running a corn sugar front, and this newly created legal vacuum around alcohol, that the group calling itself the sugar house boys began to transform into something more organised, more ambitious, and considerably more dangerous.
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[SPEAKER_00]: As the 1920s began in earnest,
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[SPEAKER_00]: The young men who had once stolen fruit of pushcards started turning their attention toward a much more lucrative target, the liquor itself, and specifically the liquor that other more established bootleggers were already smuggling in from across the river.
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[SPEAKER_00]: This is an important detail.
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[SPEAKER_00]: because it tells you something about how this particular gang initially made its name.
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[SPEAKER_00]: They did not begin primarily as producers of illegal alcohol, nor even as the original importers of it.
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[SPEAKER_00]: They began, first and foremost, as hijackers.
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[SPEAKER_00]: Older, more established, run running operations.
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[SPEAKER_00]: Many of them run by Anglo-Detrouters, or Italian-American operators, who had gotten into the business first.
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[SPEAKER_00]: would arrange a shipment of Canadian whiskey to cross the Detroit River.
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[SPEAKER_00]: Only to have that shipment ambushed on the American side by a group of extremely young, extremely aggressive gunmen who had somehow learned exactly when and where the shipment would land.
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[SPEAKER_00]: The Sugar House boys quickly gained a reputation up and down the Detroit waterfront as ruthless efficient thieves, willing to use violence without much hesitation, stealing loads of liquor that rival gangs had already gone to considerable trouble and expense to smuggle across the border.
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[SPEAKER_00]: Because their victims were themselves engaged in illegal activity, they rarely reported these thefts to police, which meant this new gang could operate with a surprising degree of impunity at least in these early years.
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[SPEAKER_00]: It's around this period in the early to mid-1920s that the name most people know this group by finally emerged and here we should pause because the true origin of the name purple gang
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[SPEAKER_00]: is genuinely uncertain, and historians have documented at least five different competing explanations, none of which can be definitively proven over the others.
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[SPEAKER_00]: One version holds that local shopkeepers describing the gang's members as Rotten, spoiled, tainted, off-color, essentially bad through and through, use the word purple as slang for damaged goods.
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[SPEAKER_00]: and the label stuck.
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[SPEAKER_00]: Another version connects the name to an early leader of the loose confederation, a man named Samuel Cohen, who reportedly went by the nickname Sammy Purple, and around whom some of the earliest iterations of the gang had organised.
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[SPEAKER_00]: before the Bernstein brothers rose to prominence.
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[SPEAKER_00]: A third version claims the name came from a purple sweater worn by a member at a meeting, where the group was deciding whether to abandon the sugar house boy's name.
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[SPEAKER_00]: A fourth traces it to a taxi cab company called the Purple Line.
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[SPEAKER_00]: whose drivers the gang allegedly used as muscle during a local trade war and a fifth which will return to later in this story ties the name to purple dye used to destroy the clothing of business owners who refuse to cooperate with the gang during a later chapter of extortion known as the cleaners and diers war
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[SPEAKER_00]: The truth is we may never know for certain which explanation is accurate, or whether it was some combination of several of them.
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[SPEAKER_00]: Each reinforcing the others, until purple gang, simply became the name that stuck in newspapers, in police reports, and in the frightened conversations of ordinary Detroiters.
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[SPEAKER_00]: What matters for our purposes is that by the middle of the 1920s, this once loose cluster of neighborhood boys from Little Jerusalem, having learned the liquor trade first as hijackers, then increasingly, as smugglers and distributors in their own right, had become known across the city, and increasingly across the entire country, by a single ominous name, the purple gang,
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[SPEAKER_00]: such as it was, had by this point consolidated around a burn steam, the eldest of the four brothers, who functioned less as a traditional mob boss barking orders, and more as a behind-the-scenes strategist and diplomat.
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[SPEAKER_00]: The kind of figure who negotiated alliances and smoothed over disputes, rather than personally pulling triggers.
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[SPEAKER_00]: His younger brothers, Ray, Joe and Izzy, along with the other original members from Bishop School and the surrounding streets,
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[SPEAKER_00]: Unlike the tightly hierarchical Sicilian crime families that would later dominate American organised crime, the purple gang remained, throughout its existence, a genuinely loose confederation.
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[SPEAKER_00]: Individual members were often essentially freelance operators, willing to hire themselves out for whichever job paid the most, whether that meant running liquor, collecting debts,
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[SPEAKER_00]: branching out into an entire menu of other rackets, gambling, wire services for horse racing results, narcotics distribution, jewelry theft and labour racketeering.
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[SPEAKER_00]: This looseness gave the purple gang a certain flexibility and reach that more rigid organisations lacked.
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[SPEAKER_00]: It also meant the gang was, in a very real sense, perpetually overextended, with individual members pursuing their own side ventures, their own grudges, and their own alliances.
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[SPEAKER_00]: Sometimes in ways that put the entire organisation at risk, we'll see exactly how that overextension played out as our story continues.
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[SPEAKER_00]: But by the mid-1920s, none of that instability was yet visible from the outside.
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[SPEAKER_00]: But from the outside, all that Detroit could see was a group of young, ferociously violent men, who had, in the span of just a few years, transformed themselves from petty neighborhood delinquents into the single most feared criminal organization the city had ever known.
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[SPEAKER_00]: and who were now turning their full attention toward the most valuable half mile of water in the entire American underworld.
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[SPEAKER_00]: The narrow cold channel of the Detroit River separating a bone dry United States from a Canadian province where
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[SPEAKER_00]: remarkably, the whiskey never stopped flowing.
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[SPEAKER_00]: That river, and the extraordinary smuggling operation the purple gang would come to dominate along its banks, is where we're headed next.
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[SPEAKER_00]: Chapter 2, the Windsor Detroit Funnel
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[SPEAKER_00]: Look at a map of the Great Lakes region, and you'll notice something that made Detroit Michigan almost destined to become the most important smuggling corridor in the history of American prohibition.
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[SPEAKER_00]: The city sits directly across a narrow waterway from Windsor on Tereo, in Canada, separated by the Detroit River, a channel that connects Lake St.
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[SPEAKER_00]: that river is barely half a mile wide.
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[SPEAKER_00]: On a clear day, you could stand on the Detroit River front and see individuals moving around on the Windsor docks on the opposite shore.
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[SPEAKER_00]: And on the other side of that half mile of water, sat something extraordinarily valuable to a thirsty, newly dry United States.
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[SPEAKER_00]: a fully legal, fully operational Canadian liquor industry, including the massive high-room Walker Distillery in Windsor.
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[SPEAKER_00]: one of the largest and most respected whiskey producers on the entire continent.
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[SPEAKER_00]: Here is the detail that made this whole arrangement possible.
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[SPEAKER_00]: And it's a detail that gets lost in a lot of popular retellings of prohibition history.
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[SPEAKER_00]: Canada, and specifically the Province of Ontario, did have its own prohibition law on the books during this period, known as the Ontario Temperance Act.
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[SPEAKER_00]: which was in effect from 1916 through 1927, but that Canadian law prohibited the sale and consumption of alcohol within Ontario.
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[SPEAKER_00]: It did not prohibit the manufacture of alcohol and crucially
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[SPEAKER_00]: It did not prohibit the export of alcohol to other countries.
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[SPEAKER_00]: This was a loophole of almost unbelievable size.
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[SPEAKER_00]: Canadian distilleries could legally produce as much whisky as they wanted, and legally sell it for export.
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[SPEAKER_00]: So long as the paperwork claimed it was headed somewhere outside of Canada.
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[SPEAKER_00]: Nobody in the Ontario government was terribly concerned with double-checking whether a given shipment of whiskey officially bound for some place like Cuba, Mexico, Bermuda, or the tiny French island territory of St. Pierre and Michelon, off the coast of Newfoundland.
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[SPEAKER_00]: actually ended up in any of those places.
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[SPEAKER_00]: And so, almost overnight, the Windsor Docks along the Detroit River sprouted a new kind of small business, export houses.
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[SPEAKER_00]: These were often nothing more than simple wooden shades thrown up along the riverbank.
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[SPEAKER_00]: staffed by enterprising Windsor businessmen who understood exactly what was happening just a half mile away in bone dry Detroit.
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[SPEAKER_00]: Trucks loaded with legally distilled Canadian whiskey would arrive at these export dogs protected by a piece of paperwork known as a B-13 customs clearance form which listed some far off destination as the shipments official endpoint.
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[SPEAKER_00]: dock workers would then load the liquor onto small boats, robots, motorboats, whatever was available, and those boats would supposedly set off toward Cuba or Venezuela, or wherever the paperwork claimed.
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[SPEAKER_00]: Instead, of course, they simply made the short crossing, sometimes only a matter of minutes, straight across the Detroit River, and unloaded their cargo
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[SPEAKER_00]: One historical account notes that a single boat driver making this short illegal run could earn as much as $200 for a single trip and enormous sum of money for a single day's work in the 1920s.
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[SPEAKER_00]: This entire stretch of contested water and riverfront, running along the Detroit River up through Lake St. Claire and covering the various smaller waterways connecting Michigan and the Canadian Province of Ontario, came to be known.
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[SPEAKER_00]: both in newspapers of the era and among historians ever since, as the Windsor Detroit funnel.
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[SPEAKER_00]: The word funnel is exactly right.
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[SPEAKER_00]: Every drop of illegal liquor destined for the massive American market.
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[SPEAKER_00]: funneled down through this one narrow crossing point, the way water funnels down through the neck of a bottle, and the numbers involved are genuinely staggering.
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[SPEAKER_00]: By the late 1920s, historians estimate that fully 75% of all the alcohol smuggled into the United States during the entire prohibition era.
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[SPEAKER_00]: crossed the border specifically at this one funnel between Windsor and Detroit.
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[SPEAKER_00]: By 1929, rum running had become Detroit's second largest industry, trailing only the automobile manufacturing that had built the city in the first place, generating an estimated $215 million a year, an astronomical figure for the period.
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[SPEAKER_00]: All of that money needed to be absorbed somewhere on the American side and by this point in our story, the organization best positioned to absorb it, control it, and defend it from rivals was the purple game.
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[SPEAKER_00]: Now, let's talk about how the actual smuggling worked, because the sheer creativity and adaptability that Detroit River Rum Run has brought to this problem, is honestly one of the more remarkable stories in the entire history of American crime.
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[SPEAKER_00]: Smuggling methods shifted with the seasons, the weather, and the ever-evolving efforts of law enforcement,
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[SPEAKER_00]: and rum runners on both sides of the river treated the whole enterprise almost like a competitive sport.
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[SPEAKER_00]: Constantly innovating new ways to outwit customs agents, Coast Guard patrol boats, and Michigan State Police.
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[SPEAKER_00]: In warmer months, when the river ran open and free of ice, the preferred method was simple speed.
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[SPEAKER_00]: fast, low-profile speedboats, some of them specially modified with powerful engines would make the crossing from Windsor to Detroit in a matter of minutes, undercover of darkness whenever possible, though plenty of runs happened in broad daylight too.
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[SPEAKER_00]: especially once bribery of customs officials became routine.
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[SPEAKER_00]: Boats would signal to one another using small handheld lights.
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[SPEAKER_00]: A blue light flashed once and then twice.
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[SPEAKER_00]: Might mean the coast was clear on the far shore.
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[SPEAKER_00]: While a sheet hung out on a closed line near a dock, might serve as a silent warning that police had arrived and the run should be aborted.
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[SPEAKER_00]: Rumrunner's waited in the trees and tall grass along both banks of the river, watching for these signals, coordinating drop points that shifted constantly to avoid detection.
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[SPEAKER_00]: Winter, though, was in some ways even more remarkable, because winter turned the Detroit River and the neighbouring Lake St. Claire into something Rumrunner's called an ice bridge.
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[SPEAKER_00]: When the water froze solid enough to support weight, smugglers simply drove directly across it.
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[SPEAKER_00]: They favored a particular type of lightweight automobile for this purpose.
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[SPEAKER_00]: Nicknamed the Whiskey Six.
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[SPEAKER_00]: Because of its smaller, lighter, six-cylinder engine, which put less strain on the ice than a heavier vehicle would.
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[SPEAKER_00]: Drivers would load these cars with cases of Canadian whiskey and simply drive straight across the frozen river
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[SPEAKER_00]: Sometimes racing directly past astonished police officers who had no reliable way to give chase, since even the fastest patrol cars struggle to keep pace with ice boats and light vehicles skimming across a frozen surface.
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[SPEAKER_00]: Some smugglers dispense with cars entirely, and instead had skaters drag loaded sleds behind them across the ice.
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[SPEAKER_00]: Photographs survive from the period showing cars that broke through weak patches of ice and sank.
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[SPEAKER_00]: Cargo and driver alike vanishing into the freezing water below.
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[SPEAKER_00]: The risk was simply factored into the cost of doing business.
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[SPEAKER_00]: Smugglers on both sides of the operation developed an almost endless variety of concealment tricks as well.
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[SPEAKER_00]: There's a wonderful, almost comic account from May of 1920 that captures the resourcefulness at play here.
30:14
[SPEAKER_00]: A man got off the Windsor ferry in Detroit, carrying a large market basket, and was struck by a passing taxi cab near the foot of Woodward Avenue.
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[SPEAKER_00]: As a crowd gathered around the accident, people in the crowd began sniffing the air, catching an unmistakable whiff of whiskey, and noticed dozens of broken eggs scattered across the pavement from the man's dropped basket.
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[SPEAKER_00]: As soon as a police officer approached a help, the injured man scrambled to his feet and fled the scene entirely, abandoning his basket.
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[SPEAKER_00]: When the officer finally examined what was left behind, he discovered that the eggs had each been carefully emptied of their contents, filled with liquor instead, and painstakingly resealed.
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[SPEAKER_00]: It's a small, almost charming detail in another wise dark story.
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[SPEAKER_00]: But it tells you something important about the sheer scale and ingenuity of the smuggling culture that had taken root along this river.
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[SPEAKER_00]: Ordinary people, not just hardened criminals, found ways to participate in the trade.
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[SPEAKER_00]: larger operations were, naturally, far more organised than a single man with a basket of doctored eggs.
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[SPEAKER_00]: One especially important smuggling operation working the Detroit Riverfront was known as the Little Jewish Navy.
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[SPEAKER_00]: A crew that operated its own fleet of boats specifically dedicated to waterborne smuggling.
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[SPEAKER_00]: The Little Jewish Navy worked sometimes on behalf of the purple
31:53
[SPEAKER_00]: moving liquor under contract for the larger organization, and at other times operated somewhat independently, occasionally even in direct competition with the purples.
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[SPEAKER_00]: This relationship, cooperative in some moments, and adversarial in others, would eventually have serious and violent
32:14
[SPEAKER_00]: that we'll get to later in our story.
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[SPEAKER_00]: When we reached the chapter, covering an event that took place at an apartment building called Collingwood Manor.
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[SPEAKER_00]: For now, it's enough to understand that the Detroit River Rum running trade was never a single monolithic operation run by one gang alone.
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[SPEAKER_00]: It was a sprawling overlapping ecosystem of independent boat crews,
32:44
[SPEAKER_00]: with the purple gang increasingly positioned at the centre of it all.
32:49
[SPEAKER_00]: Controlling the flow of product, taking a cut wherever they could, and using violence to enforce their position whenever necessary.
32:58
[SPEAKER_00]: Another popular unloading point along the Detroit Riverfront was located at the foot of Rhea Pell Street.
33:05
[SPEAKER_00]: Conveniently situated almost directly across the water
33:13
[SPEAKER_00]: According to some accounts from the period, crates of liquor were occasionally winched directly along the riverbed itself, using underwater cable systems to avoid detection entirely on the surface of the water.
33:28
[SPEAKER_00]: Whether every detail of these underwater winch stories is entirely accurate,
33:34
[SPEAKER_00]: is difficult for historians to verify with complete certainty, but the fact that such elaborate methods were even rumored gives you a sense of just how sophisticated and how well funded this smuggling economy had become by the mid to late 1920s.
33:53
[SPEAKER_00]: There was notably no bridge connecting Detroit and Windsor for almost this entire period.
34:01
[SPEAKER_00]: The Ambassador Bridge, which today carries an enormous volume of legitimate commercial traffic between the two cities, did not open until November of 1929, meaning that for nearly the entire span of prohibition, every single gallon of liquor crossing at this funnel had to make the trip by boat, by ice, or eventually
34:26
[SPEAKER_00]: Once a rail tunnel was completed, connecting the two cities, concealed among legitimate freight.
34:34
[SPEAKER_00]: Before that tunnel and that bridge existed, it was entirely boats, ice roads, bribed custom stamps, and sheer human ingenuity, night after night, for years on end.
34:46
[SPEAKER_00]: And what did all of this mean practically speaking?
34:50
[SPEAKER_00]: for the city of Detroit itself.
34:52
[SPEAKER_00]: It meant an explosion of illegal drinking establishments.
34:56
[SPEAKER_00]: A Detroit newspaper estimated in 1928 that there was somewhere between 16,000 and 25,000 speed keys and blind pigs, as illegal bars were often called, operating across the greater Detroit metropolitan area.
35:14
[SPEAKER_00]: These ranged from grim hidden rooms in slum neighbourhoods to elegant, discreet establishments, serving some of the city's most prominent citizens.
35:26
[SPEAKER_00]: A popular password of the era used to gain entry into many of these hidden clubs.
35:31
[SPEAKER_00]: was the phrase Joe sent me, a simple code that supposedly opened doors across the entire city.
35:39
[SPEAKER_00]: With that volume of demand and that volume of supply flowing in from across the river, Detroit essentially transformed almost overnight into one enormous semi-open marketplace for illegal alcohol.
35:53
[SPEAKER_00]: and the organisation best equipped to profit from managing that marketplace, taxing it, defending it, and occasionally stealing from it outright, was, again and again, the purple game.
36:08
[SPEAKER_00]: It's worth mentioning here as well, the relationship that developed between the purple game and organised crime in Chicago.
36:16
[SPEAKER_00]: and specifically with Al Capone, perhaps the single most famous gangster of the entire prohibition era.
36:25
[SPEAKER_00]: As the purple gangs control over Detroit's share of the Windsor Detroit funnel solidified through the mid 1920s.
36:33
[SPEAKER_00]: Capone's organization in Chicago found itself needing a steady, reliable supply of quality, Canadian whiskey.
36:42
[SPEAKER_00]: Rather than attempt to muscle into Detroit territory and fight the purple gang directly for control of the river, something Capone was fully capable of attempting, given the size and resources of his own organization, Capone instead chose a different path, partnership.
37:00
[SPEAKER_00]: The Purple Gang's reputation for extreme, almost casual violence, had by this point, become so well established that Capone reportedly decided a turf war simply wasn't worth the cost, even for an organization as powerful as his own.
37:19
[SPEAKER_00]: Instead, the two organizations struck a business arrangement.
37:24
[SPEAKER_00]: With the Purple Gang supplying Capone's Chicago operation with Canadian whisky, including a particular brand known as Old Log Cabin, for a period of several years, it's a small but telling detail about just how seriously the rest of the American underworld took the Purple Gang's reputation.
37:45
[SPEAKER_00]: This wasn't a minor regional outfit.
37:48
[SPEAKER_00]: This was an organisation whose violent capabilities were respected and feared.
37:55
[SPEAKER_00]: Even by the most powerful crime boss in the entire country, none of this could have operated at the scale it did, without a deep and pervasive culture of corruption on both sides of the river.
38:08
[SPEAKER_00]: Customs officials,
38:09
[SPEAKER_00]: whose entire job was to verify that shipments like those B-13 export forms were legitimate, were bribed so routinely that historians of the period describe the practice as close to an open secret, simply another operating cost baked into the price of doing business.
38:32
[SPEAKER_00]: Some accounts from the era suggest that as much as one quarter of the population living near the Detroit River on the Ontario side had some hand in the liquor trade in one form or another, whether running boats, watching for police patrols, or simply looking the other way.
38:50
[SPEAKER_00]: On the American side, the United States Coast Guard did maintain a rum patrol along the Detroit River and the wider Great Lakes, attempting to intercept smuggling boats before they reached shore.
39:05
[SPEAKER_00]: And Michigan State Police did their best to chase down whisky sixes racing across the winter ice.
39:14
[SPEAKER_00]: But the sheer geography of the crossing worked against them
39:19
[SPEAKER_00]: A half mile of open water can be crossed by a fast boat in only a few minutes, which left interception patrols only the narrowest possible window to act, and state police pursuit cars, however fast on pavement, simply could not keep pace with a light vehicle, or a nice boat skimming across a frozen river, tyre chains, or no tyre chains.
39:45
[SPEAKER_00]: Detroit's own police department
39:48
[SPEAKER_00]: was hardly immune to the same currents of corruption flowing through every other layer of this economy, and prosecutions of high-ranking gang figures for their role in the river trade itself remained frustratingly rare throughout the entire decade, even as the newspapers openly speculated
40:09
[SPEAKER_00]: about which officials might be on whose payroll.
40:12
[SPEAKER_00]: It's worth remembering, too, just how much ordinary public sentiment worked in the smugglers' favor.
40:21
[SPEAKER_00]: National Prohibition enacted through the 18th Amendment and enforced under the Volstead Act, had always rested on a genuinely divided public opinion, and in a hard-drinking heavily immigrant industrial city like Detroit, that divide tilted overwhelmingly against the law itself.
40:41
[SPEAKER_00]: Ordinary Detroiters were, in enormous numbers, willing customers of the illegal liquor trade.
40:48
[SPEAKER_00]: patronizing those 16,000 to 25,000 species without much sense that they were doing anything particularly shameful.
40:57
[SPEAKER_00]: That broad public tolerance meant purple gang smugglers and rarely had to worry about ordinary citizens turning them in and it meant that law enforcement even when it
41:13
[SPEAKER_00]: was often fighting an uphill battle against a public that simply did not view the underlying activity as a serious crime, whatever the federal statute book said.
41:24
[SPEAKER_00]: It's a genuinely important piece of context for understanding why an organisation as violent and as visible as the purple gang could operate for so long with such relative impunity.
41:37
[SPEAKER_00]: They weren't just evading the law
41:41
[SPEAKER_00]: across large parts of Detroit, they were quietly supplying a public that wanted exactly what they were selling.
41:48
[SPEAKER_00]: By the late 1920s then, the picture looked something like this, a narrow half mile of water.
41:56
[SPEAKER_00]: Quietly carrying three quarters of the nation's illegal liquor supply, a booming chaotic ecosystem of boats, trucks, ice bridges, bribe officials, and improvised concealment tricks.
42:10
[SPEAKER_00]: A city absolutely saturated with speak-eases, all of them hungry for product, and at the centre of it, increasingly, a single organisation.
42:21
[SPEAKER_00]: A gang that had started as a handful of neighborhood boys stealing fruit of pushcarts.
42:28
[SPEAKER_00]: Now controlling one of the most lucrative illegal enterprises in the history of American organised crime.
42:36
[SPEAKER_00]: Generating money on a scale that dwarfed anything their immigrant parents could ever have imagined for them.
42:43
[SPEAKER_00]: But money on that scale and power on that scale rarely stays peaceful for long, and it's here as the purple gangs wealth and influence reach their absolute peak that our story turns darker into a series of increasingly brutal conflicts, both with rivals outside the organisation, and eventually, from within it.
43:10
[SPEAKER_00]: Chapter 3 Blood on Hastings Street.
43:16
[SPEAKER_00]: Every criminal organisation that grows large enough and wealthy enough eventually starts looking for new territory to expand into and the purple gang flush with cash from the river trade was no exception.
43:31
[SPEAKER_00]: Around 1925, the gang's attention turned toward an industry that, on its face, seems almost absurdly unrelated to bootlegging.
43:40
[SPEAKER_00]: The professional laundry business,
43:43
[SPEAKER_00]: specifically the cleaners and diers who handled dry cleaning and clothing care for businesses and individuals across Detroit.
43:50
[SPEAKER_00]: The back story here involves genuine economic instability within the laundry industry itself.
43:57
[SPEAKER_00]: By 1924, Detroit's professional cleaning and dying companies were caught in a punishing cycle of price competition,
44:11
[SPEAKER_00]: was turning a healthy profit.
44:14
[SPEAKER_00]: Adding to the trouble, tailors and other customers frequently failed to pay their cleaning bills on time.
44:21
[SPEAKER_00]: Sometimes simply taking their business elsewhere rather than settling what they owed.
44:27
[SPEAKER_00]: Legitimate business owners in the industry genuinely wanted some kind of organisation, some kind of trade association that could stabilise pricing
44:41
[SPEAKER_00]: That desire for legitimate organization created an opening and Abe Bernstein always the gang's most strategic mind saw it immediately.
44:52
[SPEAKER_00]: Working in partnership with a local Labour leader named Francis X Martell, President of the Detroit Federation of Labour, Abe Bernstein, helped form an organisation called the wholesale cleaners and diers association.
45:08
[SPEAKER_00]: On paper, this was simply a trade group meant to bring order and fair pricing to a chaotic industry.
45:16
[SPEAKER_00]: In practice, it quickly became a vehicle for extortion,
45:20
[SPEAKER_00]: with the purple gang in forcing membership through violence and intimidation, cleaning and dying businesses that decline to join the association, found gang members showing up at their monthly meetings anyway, collecting Jews, whether the business owner had agreed to pay them or not, as long as those Jews kept flowing.
45:44
[SPEAKER_00]: the gang generally left a business alone.
45:47
[SPEAKER_00]: Businesses that refuse to pay or refuse to join at all, found themselves targeted by an escalating campaign of intimidation.
45:56
[SPEAKER_00]: Stink bombs thrown into laundry facilities to ruin goods and drive away customers.
46:02
[SPEAKER_00]: Bricks thrown through windows, sticks of dynamite left, half burned, outside plant doors, as unmistakable warnings.
46:12
[SPEAKER_00]: business owners who spoke out publicly against the association, risked physical assault.
46:18
[SPEAKER_00]: On October 26, 1925, two independent businesses that had refused to cooperate.
46:27
[SPEAKER_00]: the novelty cleaners and diers company, and the empire cleaners and diers company were both bombed.
46:34
[SPEAKER_00]: Around the same period, two of the associations most vocal opponents, men named Sam Sigmund and Samuel Pollakov, were murdered.
46:44
[SPEAKER_00]: According to some accounts of this period,
46:46
[SPEAKER_00]: purple dye was specifically used, again and again, to ruin the clothing of businesses that refuse to cooperate with the gang-controlled association, an image so vivid that, as we discussed earlier, some historians believe it may have contributed to the gangs enduring nickname.
47:05
[SPEAKER_00]: This campaign
47:06
[SPEAKER_00]: which came to be known as the Cleaners and Dyer's War, continued for roughly three years.
47:13
[SPEAKER_00]: From 1925 through 1928, funding the gang's broader operations and giving its members valuable experience in the mechanics of organized extortion, skills they would apply again and again in the years that followed.
47:32
[SPEAKER_00]: It finally came to a head in 1928 when a business owner named Charles Jacobi Junior, along with a total of 13 members of the Purple Gang, including Abe and Ray Bernstein.
47:45
[SPEAKER_00]: Irving Milberg, Eddie Fletcher, a man known as Joe Honeyboy Miller.
47:51
[SPEAKER_00]: Irving Shapiro, a man named Abe Kaminsky, and brothers Abe and Simon Axler were formally charged with conspiracy to extort money in connection with the wholesale cleaners and diers association.
48:07
[SPEAKER_00]: A key witness in that trial was a man named Harry Rosman, president and owner of a legitimate business called famous cleaners and diers, who testified that the gang had demanded $1,000 per week from his business alone in exchange for so-called protection, despite Rosman's damaging testimony and despite what most contemporary observers understood to be an overwhelming case.
48:37
[SPEAKER_00]: Every single defendant was found not guilty and fully acquitted.
48:42
[SPEAKER_00]: It's worth sitting with that outcome for a moment because it tells you something important.
48:48
[SPEAKER_00]: about the position the purple gang had reached by this point in Detroit's history.
48:53
[SPEAKER_00]: Witnesses were terrified of retaliation, juries, for whatever combination of reasons, whether fear, bribery, or simple inability to secure a unanimous verdict against defendants who had powerful and well-resourced legal representation declined to convict.
49:18
[SPEAKER_00]: seemed only to confirm its near total immunity from the ordinary machinery of law enforcement and criminal justice.
49:27
[SPEAKER_00]: Historians of this period often describe what followed as the purple gangs' golden period.
49:33
[SPEAKER_00]: Roughly the year surrounding 1928 and 1929.
49:38
[SPEAKER_00]: When the organization controlled gambling, liquor, narcotics, and now labor racketeering across Detroit, seemingly answerable to absolutely nobody, it's worth spending a moment on exactly what that golden period looked like in practice.
49:57
[SPEAKER_00]: because it's easy telling this story to focus so heavily on the liquor trade and the killings that the sheer breadth of the gang's operations gets lost.
50:08
[SPEAKER_00]: By the late 1920s, the purple gang's fingers reached into an enormous range of Detroit's underworld economy.
50:17
[SPEAKER_00]: They ran a horse racing wire service supplying up to the minute race results to gambling parlors across the city.
50:25
[SPEAKER_00]: a surprisingly lucrative racket in an era before television or instant communication made such information easy to come by.
50:36
[SPEAKER_00]: They operated numbers games and other gambling rackets throughout Detroit, including
50:43
[SPEAKER_00]: according to several historical accounts, gambling operations, specifically targeting the city's growing African-American population on the Near East side.
50:54
[SPEAKER_00]: A detail that speaks to how thoroughly the gang had expanded beyond its original neighborhood routes and into every corner of the city's underground economy, and they had, by this point, moved decisively into narcotics distribution as
51:11
[SPEAKER_00]: In May of 1929, several purple gang members were arrested in photographed, faces turned away from the camera, on charges connected to providing protection for Detroit area narcotics dealers, one of several instances where law enforcement caught at least a glimpse of just how far the organization's criminal reach had extended beyond the liquor trade that had made its early reputation.
51:38
[SPEAKER_00]: Add to all of this, the ongoing extortion income still flowing from the laundry industry and you begin to understand why, by the late 1920s, contemporary newspaper estimates placed the purple gangs total earnings in the millions of dollars annually, an almost unimaginable sum for a group of men who, only a decade earlier, had been stealing fruit off pushcards in Little Jerusalem,
52:08
[SPEAKER_00]: But even during this so-called golden period, the seeds of much greater violence were already being planted.
52:15
[SPEAKER_00]: This time, not against legitimate businesses, but against rival criminals encroaching on purple gang territory.
52:24
[SPEAKER_00]: By the mid-1920s, the purple gang had formed a working alliance with a group of former members
52:32
[SPEAKER_00]: of a St. Louis criminal organization known as Egan's Rats.
52:38
[SPEAKER_00]: Most notably two men named Fred Killer Burke and Gus Winkler.
52:43
[SPEAKER_00]: Burke and Winkler, along with several associates, worked as enforcers and strong arm operatives on the Purple Gang's behalf, handling distribution and any violent work the situation required.
52:57
[SPEAKER_00]: Trouble began on Christmas night of 1926, when a saloon keeper and liquor agent for the purples named Johnny Reed was shot to death with a shotgun in the rear of his own apartment building.
53:11
[SPEAKER_00]: Reed, himself a former member of Egan's Rats, had earlier that year been involved in a shooting conflict with a Sicilian gangster named Mike Depesa.
53:22
[SPEAKER_00]: And while Depesa's side had lost that earlier confrontation, suspicion quickly fell on Depesa's associates as the likely orchestrators of Reed's Christmas night murder in revenge.
53:37
[SPEAKER_00]: The Prime Suspect, in carrying out that killing, was believed to be a Chicago-based jewel thief named Frank Wright, who had recently relocated to Detroit, working alongside two New York burglars named Joseph Bloom and George Cohen.
54:01
[SPEAKER_00]: several of whom had direct connections to the Purple Gang.
54:05
[SPEAKER_00]: The situation escalated dramatically on February 3rd, 1927, when Wright, Bloom, and Cohen gunned down a Purple Gang drug distributor named Jake Weinberg in Detroit's North End neighborhood.
54:21
[SPEAKER_00]: This was, from the Purple Gang's perspective, a line that could not be allowed to stand unanswered.
54:29
[SPEAKER_00]: The Bernstein brothers
54:30
[SPEAKER_00]: as the gang's recognised leaders hired Fred Burke and Gus Winkler specifically to avenge Weinberg's murder and the plan they devised was as cold as it was effective.
54:43
[SPEAKER_00]: Wright had a close friend named Maya Fish Bloomfield and the plot has arranged to kidnap Bloomfield's bait.
54:51
[SPEAKER_00]: Winkler then telephone right directly and told him he could recover his kidnapped friend at apartment number 308 of the Milaflore's apartment.
55:03
[SPEAKER_00]: Located at the address 106 East Alexander Avenue in Detroit.
55:09
[SPEAKER_00]: At 430 in the morning on March 28th,
55:13
[SPEAKER_00]: 1927, right arrived at the Miller-Flore's apartments, along with Bloom and Cohen, and knocked on the door of apartment 308, exactly as arranged.
55:27
[SPEAKER_00]: As they stood in the hallway waiting, a fire door at the end of the corridor swung open, and three gunmen opened fire with a concentrated volley of pistol fire and notably a Thompson sub-machine gun.
55:44
[SPEAKER_00]: One of the very first documented uses of a Tommy gun in a Detroit underworld killing.
55:50
[SPEAKER_00]: All three men, Wright, Bloom and Cohen fell dead in the hallway.
55:56
[SPEAKER_00]: The Triggerman escaped down a rear stairwell before police could arrive.
56:01
[SPEAKER_00]: This event became known as the Miller-Flora's massacre, and while it was widely suspected to be the work of the purple gang, acting through their hired enforcers, Burke and Winkler, no convictions were ever secured.
56:16
[SPEAKER_00]: Several days after the killing, A burned steam himself surrendered to police and posted a modest bond of $500 for his appearance, and once again, as had happened with the cleaners
56:32
[SPEAKER_00]: all of the purples connected to the case were ultimately acquitted.
56:36
[SPEAKER_00]: The Milaflora's massacre, rather than weakening the gang's position, seemed only to reinforce a growing sense within the organization that they were for all practical purposes untouchable.
56:50
[SPEAKER_00]: That feeling of invincibility would carry the purple gang through its most powerful years, but it would also eventually
56:58
[SPEAKER_00]: contribute directly to the organisations on doing, because an organisation that believes itself untouchable tends to grow careless and carelessness in this particular line of work tends to prove fatal, which brings us to the single event most historians point two as the true turning point in the purple gang's story.
57:20
[SPEAKER_00]: The Collingwood Manomassica of September 16,
57:28
[SPEAKER_00]: The purple gangs internal structure, always loose, always more of a confederation of independent operators than a disciplined hierarchy, had begun showing serious strain.
57:39
[SPEAKER_00]: A small affection, operating loosely under the purple gangs broader umbrella.
57:45
[SPEAKER_00]: Sometimes associated with the little Jewish navy boat crews we discussed earlier.
57:50
[SPEAKER_00]: had developed its own internal tensions.
57:53
[SPEAKER_00]: Three men in particular, Joseph Lebewitz, known by an unfortunately common racial nickname of the period that historical records preserve, but that we won't repeat here.
58:04
[SPEAKER_00]: Herman Heimi Paul and Isadora Izzy, the Rat Sutka, had.
58:10
[SPEAKER_00]: According to most accounts, these men had been accused of withholding profits, owed to the broader purple gang organization.
58:18
[SPEAKER_00]: from their end of the liquor smuggling business.
58:22
[SPEAKER_00]: There's also a competing account, worth mentioning for the sake of historical completeness, suggesting these same three men had earlier traveled to Chicago and attempted to extort protection money from speak easy operators there.
58:37
[SPEAKER_00]: unaware that those particular Chicago establishments were already under the protection of Al Capone's organization.
58:46
[SPEAKER_00]: When Capone discovered the shakedown, he reportedly gave the three men a blunt choice, leave Chicago immediately or leave it in a coffin.
58:55
[SPEAKER_00]: They chose to leave willingly, relocating to Detroit, where they eventually became associated with the little Jewish Navy
59:04
[SPEAKER_00]: Whichever version of events led up to it, by the late summer of 1931, Leberwitz, Paul, and Sutka had crossed the Purple Gang's leadership in some significant, unforgivable way, and Ray Bernstein, one of the four founding brothers, made the decision that they needed to be eliminated.
59:27
[SPEAKER_00]: Ray Bernstein devised a plan that relied on a mutual friend and go between, named Solovine, a man trusted by both the Purple Gang leadership, and by Leberwitz, Paul, and Sutko themselves.
59:42
[SPEAKER_00]: The plotters rented an apartment
59:44
[SPEAKER_00]: Unit 211 at a building called the Collingwood Manor Apartments, located at 1740 Collingwood Avenue in Detroit.
59:53
[SPEAKER_00]: Ray Bernstein then convinced Levine that the purple gang leadership had actually decided to formally recognize Leberwitz, Paul and Sutka as their official agents in the liquor business going forward.
1:00:08
[SPEAKER_00]: Essentially offering them a promotion and a peace settlement.
1:00:12
[SPEAKER_00]: An asked Levine to help arrange a friendly meeting to finalise the new arrangement.
1:00:19
[SPEAKER_00]: On the afternoon of September 16, 1931, Levine drove the three men to the Collingwood Manor apartments for what they believed was this peace conference.
1:00:31
[SPEAKER_00]: Inside apartment 211, several purple gang members were waiting, including Harry Flycher, Irving Milberg, Harry Keywell, and Ray Bernstein himself.
1:00:45
[SPEAKER_00]: After a brief, superficially friendly conversation, Ray Bernstein excused himself, telling the group he needed to go start the getaway car.
1:00:56
[SPEAKER_00]: His departure was actually a signal.
1:01:00
[SPEAKER_00]: He was to wait for the sound of the car backfiring, followed by a hunk of the horn, which would be the cue for the men remaining inside the apartment to carry out the killings.
1:01:11
[SPEAKER_00]: Harry flashes stood up, drew a 38 caliber revolver, and shot Leberwitz at point-blank range.
1:01:18
[SPEAKER_00]: In the chaos that followed, Irving Milberg and Harry Keywell opened fire as well.
1:01:25
[SPEAKER_00]: And within moments, all three visitors, Leberwitz, Paul and Sutka, lay dead inside the apartment.
1:01:41
[SPEAKER_00]: He was, after all, a personal friend of Ray Bernstein, and the gang apparently calculated that his continued friendship and his silence was worth more alive than the risk of leaving one more loose end tied up permanently.
1:01:58
[SPEAKER_00]: That calculation turned out to be a catastrophic miscalculation.
1:02:04
[SPEAKER_00]: Solovine deeply shaken by what he had just witnessed, and now fully aware that his own life might still be in danger regardless of the gang's intentions, was picked up by Detroit police in the investigation that followed.
1:02:19
[SPEAKER_00]: Rather than protecting the men who had spared his life, Levina agreed to cooperate fully with prosecutors, becoming what the historical record generally
1:02:33
[SPEAKER_00]: The formal pre-trial examination began on September 30, 1931.
1:02:39
[SPEAKER_00]: Levine identified Ray Bernstein, Harry Keywell, and Irving Milberg by names the shooters.
1:02:46
[SPEAKER_00]: And further testified that Harry Fleischer had also participated in the killings.
1:02:52
[SPEAKER_00]: Though fly sure himself managed to avoid capture and was not present to stand trial alongside the others.
1:03:00
[SPEAKER_00]: Ray Bernstein, Harry Keywell and Irving Milberg were tried.
1:03:05
[SPEAKER_00]: convicted of first-degree murder and sentenced to life imprisonment for the killings at Collingwood Manor.
1:03:12
[SPEAKER_00]: Detroit's police chief of detectives at the time, a man named James McCarty, offered a blunt public assessment that has been quoted by historians ever since.
1:03:24
[SPEAKER_00]: The convictions, he said, had broken the back of the once powerful purple gang, putting an end to more than five years of what he called arrogance and terrorism.
1:03:37
[SPEAKER_00]: He predicted, correctly as it turned out, that the effect of these convictions would prove enormously influential in finally cracking the organization's grip on Detroit's underworld.
1:03:54
[SPEAKER_00]: which finally broke the Purple Gang's power wasn't a defeat.
1:03:58
[SPEAKER_00]: at the hands of police and it wasn't a defeat at the hands of a rival gang.
1:04:04
[SPEAKER_00]: It was in the end the gang's own internal betrayal.
1:04:09
[SPEAKER_00]: Its own violence turned inward against members of its own extended orbit.
1:04:14
[SPEAKER_00]: Exposed by a witness, the killers themselves had spared an out of personal loyalty that finally opened the door for law enforcement.
1:04:24
[SPEAKER_00]: and for a rising rival to bring the purple gangs rain to an end.
1:04:31
[SPEAKER_00]: Chapter 4 The Unraveling
1:04:36
[SPEAKER_00]: The convictions arising from the Collingwood Manor Massacre did not destroy the Purple Gang overnight.
1:04:43
[SPEAKER_00]: Organizations built on this much money, and this much fear rarely collapse all at once.
1:04:49
[SPEAKER_00]: What happened instead, across the early to mid-1930s, was a slower, grinding, unraveling, a steady accumulation of prison sentences, mysterious executions.
1:05:03
[SPEAKER_00]: and shifting underworld alliances that gradually stripped the gang of its manpower, its leadership and finally its territory.
1:05:15
[SPEAKER_00]: Even before Collingwood Manor, cracks had already begun appearing in the organisation in July of 1929.
1:05:23
[SPEAKER_00]: four purple gang members, Eddie Fletcher, Harry Sutton, A-Baxler and Irving Millburg were sentenced to 22 months in the federal penitentiary at Leavenworth for conspiracy to violate prohibition laws.
1:05:42
[SPEAKER_00]: That same month, another member, Irving Shapiro, one of the original boys from Bishop School back in the earliest days of the story, was taken for a ride, as the underworld euphemism of the era put it and killed.
1:05:57
[SPEAKER_00]: In 1930,
1:05:59
[SPEAKER_00]: A gang member named Morris Raider was sentenced to 12 to 15 years in Jackson's state prison after shooting a teenage boy he suspected of spying on gang members while they were cutting or diluting whiskey and then in 1931
1:06:18
[SPEAKER_00]: came the Collingwood Manor convictions themselves, removing Ray Bernstein, Harry Keywell and Irving Millberg from the streets permanently, sentenced to life imprisonment.
1:06:32
[SPEAKER_00]: With so many of the gangs most capable and feared enforcers now dead, imprisoned or in hiding.
1:06:39
[SPEAKER_00]: The remaining leadership found itself increasingly vulnerable, both to law enforcement and ominously, to other criminal organizations who could sense weakness and were beginning to circle.
1:06:54
[SPEAKER_00]: In 1931, a Bernstein himself, the gang's long-time strategic leader,
1:07:01
[SPEAKER_00]: was sentenced to 10 years in prison, not for murder or extortion, but for income tax evasion, the same charge incidentally that had brought down Al Capone in Chicago around this same period.
1:07:16
[SPEAKER_00]: It's a detail worth noting.
1:07:19
[SPEAKER_00]: because it illustrates something important about how federal authorities were increasingly approaching organized crime by this point in American history.
1:07:29
[SPEAKER_00]: When murder charges prove difficult to make stick.
1:07:32
[SPEAKER_00]: thanks to terrified witnesses and skilled defense returns, tax evasion charges, based on the simple undeniable fact that these men were living far beyond any legitimate, reported income, proved to be a far more reliable tool.
1:07:50
[SPEAKER_00]: for finally putting gang leadership behind bars.
1:07:53
[SPEAKER_00]: Meanwhile, the mysterious killings continued.
1:07:57
[SPEAKER_00]: In November of 1933, the bodies of Abe Axler and Eddie Fletcher, two men who had been core members of the gang for years.
1:08:08
[SPEAKER_00]: going back to their involvement in the cleaners and diers' war would discover together inside a car parked on an isolated country road near the intersection of Telegraph Road and Quarten Road in what is now Bloomfield Hills, Michigan.
1:08:25
[SPEAKER_00]: Both men
1:08:26
[SPEAKER_00]: had been shot numerous times in the face at extremely close range.
1:08:32
[SPEAKER_00]: The killings were never solved and remain to this day among Oakland County's most notorious unsolved cold cases.
1:08:41
[SPEAKER_00]: At the time and in the years since, most historians and law enforcement officials have concluded that the murders were most likely ordered by rising Italian-American organised crime figures.
1:08:55
[SPEAKER_00]: with the cooperation of purple gang insiders, looking to secure their own position within a rapidly shifting underworld hierarchy.
1:09:04
[SPEAKER_00]: Some accounts specifically point to lucky Luciano's expanding east coast crime syndicate, as having played a role in absorbing and in some cases eliminating the remnants of Detroit's once dominant Jewish gang.
1:09:19
[SPEAKER_00]: This is
1:09:25
[SPEAKER_00]: 1933 also happened to be the year National Prohibition finally came to an end with the ratification of the 21st Amendment repealing the 18th.
1:09:38
[SPEAKER_00]: The single most lucrative pillar of the Purple Gang's entire criminal empire.
1:09:44
[SPEAKER_00]: The illegal liquor trade that had made them rich, feared, and seemingly untouchable throughout the 1920s simply stopped being illegal.
1:09:56
[SPEAKER_00]: Overnight!
1:09:57
[SPEAKER_00]: An entire industry that had generated an estimated $215 million a year across the Windsor Detroit funnel became, essentially, ordinary legal commerce, regulated by the state rather than run by gangsters.
1:10:14
[SPEAKER_00]: The gang still had other rackets to fall back on, gambling, narcotics, extortion, labor racketeering, but none of these carried quite the same overwhelming scale, or quite the same broad public tolerance that bootlegging had enjoyed during the dry years when huge portions of the ordinary public were, in effect, willing customers of organised crime.
1:10:43
[SPEAKER_00]: that the purple gang was losing its signature business and its most capable leadership to prison sentences and unsolved murders.
1:10:53
[SPEAKER_00]: A different, more disciplined criminal organization was rising in Detroit to fill the vacuum.
1:11:00
[SPEAKER_00]: This was the beginning of what would eventually become known as the Detroit Partnership, a Sicilian-American organized crime family, led by a man named Joseph
1:11:14
[SPEAKER_00]: Unlike the Purple Gang's loose informal confederation of independent operators, the emerging Italian American organization in Detroit, modeled itself on the same, tightly hierarchical discipline structure.
1:11:33
[SPEAKER_00]: that families like it were adopting in cities across the country during this same period.
1:11:39
[SPEAKER_00]: As the broader American mafia consolidated into the more formal national crime syndicate, under figures like Lucky Luciano and Maya Lansky on the East Coast.
1:11:52
[SPEAKER_00]: A weakened, fractured purple gang.
1:11:55
[SPEAKER_00]: Its leadership scattered between prison cells and unmarked graves.
1:11:59
[SPEAKER_00]: was in no position to resist this more organised rival.
1:12:04
[SPEAKER_00]: What followed across the mid-1930s was less an open war, and more a gradual, sometimes violent transfer of territory and influence.
1:12:15
[SPEAKER_00]: Remaining purple gang associates face to start choice.
1:12:19
[SPEAKER_00]: Fall in line under the new Sicilian-led organisation.
1:12:23
[SPEAKER_00]: retire from the criminal life entirely, or in a number of documented cases simply be eliminated.
1:12:32
[SPEAKER_00]: Henry Shaw, one of the original Oakland Sugar House Mentors, who had helped launch the entire operation back in the earliest days of this story, was among those killed during this period of realignment, a purple gang associate named Harry Milman,
1:12:49
[SPEAKER_00]: became emblematic of this final chapter.
1:12:52
[SPEAKER_00]: Milman had a well-earned reputation as one of the gang's most reckless and defiant remaining members.
1:12:59
[SPEAKER_00]: Someone who continued picking fights with the rising Italian American organizations leadership.
1:13:05
[SPEAKER_00]: long after most of his former colleagues had accepted the new balance of power.
1:13:11
[SPEAKER_00]: Abe burns Dean himself, according to several historical accounts, personally attempted on multiple occasions to smooth over Millman's escalating disputes with Detroit's new Sicilian leadership, but was ultimately unable to keep the peace.
1:13:30
[SPEAKER_00]: Early in 1937,
1:13:33
[SPEAKER_00]: an attempt was made on Millman's life using dynamite planted in his car outside a night spot.
1:13:41
[SPEAKER_00]: The attempt failed to kill its intended target, though tragically it killed a parking valley instead.
1:13:48
[SPEAKER_00]: Millman's luck finally ran out on Thanksgiving Day, November 24, 1937, when he was shot to death at
1:14:03
[SPEAKER_00]: His killers were widely believed to have been professional assassins brought in specifically from Brooklyn, associated with a notorious contract killing operation that later became known to the public as murder incorporated.
1:14:18
[SPEAKER_00]: Millman's death is generally regarded by historians, as marking the definitive, final end of the purple gang.
1:14:27
[SPEAKER_00]: As any kind of independent force in Detroit's organised crime landscape, it's worth pausing here to note just how different this ending was from what one might expect.
1:14:38
[SPEAKER_00]: given everything we've described about the Purple Gang's ferocious reputation throughout the 1920s.
1:14:45
[SPEAKER_00]: There was no climactic final battle, no dramatic last-danned.
1:14:51
[SPEAKER_00]: Instead, the organisation simply wore itself down, piece by piece, through exactly the same combination of internal instability and uncontrolled violence that had characterized its rise.
1:15:05
[SPEAKER_00]: The very looseness that had once given the gang its flexibility, allowing individual members to pursue whatever opportunities paid best, also meant there was no strong central authority capable of enforcing discipline, resolving internal disputes peacefully, or negotiating a coherent unified position as a new and more organised rival rose around them.
1:15:31
[SPEAKER_00]: Compare this.
1:15:32
[SPEAKER_00]: to how a burnstein himself ultimately handled the gang's final transition of power.
1:15:39
[SPEAKER_00]: Rather than fighting a losing war to the bitter end, historical accounts describe Bernstein negotiating what amounted to one of the only genuinely peaceful transverse of underworld authority in Detroit's criminal history, essentially seeding the purple gangs remaining territory and influence to Joseph Zerrele's organization in exchange for being left alone to live out
1:16:08
[SPEAKER_00]: And that, in the end, is essentially what happened.
1:16:12
[SPEAKER_00]: By around 1935, most historians agree that the Purple Gang's power as a dominant, organized criminal force had been fully broken.
1:16:24
[SPEAKER_00]: Some individual members lingered on the margins of Detroit's underworld for a few more years.
1:16:30
[SPEAKER_00]: and the final violent death of Harry Milman in 1937 serves as a kind of closing punctuation mark on the whole story.
1:16:39
[SPEAKER_00]: But the organisation that had once controlled 75% of the nation's illegal liquor supply.
1:16:46
[SPEAKER_00]: that had partnered on equal terms with Al Capone, that had walked away from murder trial after murder trial with a quittle after a quittle.
1:16:56
[SPEAKER_00]: Had, within roughly a decade, essentially cease to exist as a meaningful, criminal power.
1:17:04
[SPEAKER_00]: Its territory, its rackets, and much of its remaining infrastructure were absorbed into what would become the Detroit partnership.
1:17:13
[SPEAKER_00]: An organisation that would go on to dominate Michigan's organised crime landscape for decades afterward, long after the purple gang itself had faded into history and legend.
1:17:25
[SPEAKER_00]: It's a genuinely sobering arc to sit with, late at night like this.
1:17:31
[SPEAKER_00]: A group of immigrant children drawn together by shared poverty and shared mischief in a crowded neighborhood, rising through sheer nerve, opportunism and violence to become one of the wealthiest and most feared criminal organizations in the entire country, controlling a river, controlling a city,
1:17:55
[SPEAKER_00]: Striking deals with the most powerful gangster in America as something close to an equal, and then within roughly a decade, dissolving almost as quickly as it had risen, undone as much by its own internal fractures as by any outside falls.
1:18:16
[SPEAKER_00]: Chapter 5.
1:18:17
[SPEAKER_00]: Echos on the river.
1:18:21
[SPEAKER_00]: Let's spend our final chapter tonight following the individual threads of this story to their ends.
1:18:28
[SPEAKER_00]: And then stepping back to consider how the purple gang has been remembered, both accurately and quite often, inaccurately.
1:18:37
[SPEAKER_00]: in the decades since prohibition finally faded into history.
1:18:43
[SPEAKER_00]: A Bernstein, the eldest of the four founding brothers, and the gang's most consistent strategic leader across its entire existence, actually lived a remarkably long life by the standards of men in his profession.
1:18:58
[SPEAKER_00]: Having negotiated that relatively peaceful handover of territory to Joseph's a really rising organisation in the mid-1930s, Bernstein largely withdrew from active criminal leadership, though he and his surviving brothers, Joe and Izzy, reportedly continued earning substantial money for years afterward through Detroit bookmaking operations and a horse racing wire service.
1:19:24
[SPEAKER_00]: Both rackets that operated in a legal gray area for much of the 20th century.
1:19:30
[SPEAKER_00]: and that required far less violent enforcement than the liquor trade once had.
1:19:36
[SPEAKER_00]: By 1939, Abe Bernstein was living comfortably in a luxury suite at the book Cadillac Hotel in downtown Detroit, a grand historic building that still stands today.
1:19:49
[SPEAKER_00]: Now operating as the Western Book Cadillac.
1:19:52
[SPEAKER_00]: At 1114, Washington Boulevard.
1:19:56
[SPEAKER_00]: According to several historical accounts, Detroit's new Sicilian-led organised crime leadership continued covering Bernstein's hotel expenses for the remainder of his life, a striking, almost courteous arrangement, given how violently that same organisation had displaced so many of Bernstein's own former associates, only a few years earlier.
1:20:23
[SPEAKER_00]: Abe Bernstein died peacefully on March 7, 1968 at around 76 years of age.
1:20:31
[SPEAKER_00]: Nearly four decades after the gang he helped build first began terrorizing the city of Detroit.
1:20:39
[SPEAKER_00]: His brothers, Izzy and Joe, meanwhile, reportedly relocated to California in their later years, quietly stepping away from the underworld entirely.
1:20:49
[SPEAKER_00]: Ray Bernstein, Harry Keywell, and Irving Milberg, the three men convicted for their roles in the Collingwood Manor Massacre, served lengthy prison sentences, following their 1931 life sentences.
1:21:04
[SPEAKER_00]: Records indicate that Harry Keywell, notably, was eventually paroled decades later in the 1960s.
1:21:13
[SPEAKER_00]: After having spent the majority of his adult life behind bars, a stark contrast to the relatively comfortable final decades enjoyed by a Bernstein.
1:21:26
[SPEAKER_00]: who had, after all, been present at the planning of the very same massacre, without ever facing prosecution for itself.
1:21:35
[SPEAKER_00]: Other members of the gang met considerably darker fates.
1:21:40
[SPEAKER_00]: As we discussed in our previous chapter, Irving Shapiro was killed in 1929.
1:21:47
[SPEAKER_00]: Abe Axler and Eddie Fletcher were murdered together in 1933.
1:21:53
[SPEAKER_00]: Their killings never solved.
1:21:55
[SPEAKER_00]: Henry Shaw, one of the two original mentors who had first taught the young sugar house boys the liquor trade back in the earliest days of this story, was killed during the mid-1930s realignment of Detroit's underworld.
1:22:11
[SPEAKER_00]: Harry Milman, the last defiant holdout.
1:22:14
[SPEAKER_00]: were shot to death at a Detroit delicatessen on Thanksgiving Day of 1937.
1:22:20
[SPEAKER_00]: Across the various historical accounts of the Purple Gang's final years, a consistent pattern emerges.
1:22:27
[SPEAKER_00]: Those who accepted the new order, who quietly stepped aside, as the more disciplined, Sicilian-American organization consolidated power across Detroit, tended to live out relatively ordinary lives.
1:22:42
[SPEAKER_00]: Those who continued fighting for territory, or defying the new hierarchy, tended not to.
1:22:48
[SPEAKER_00]: It's worth pausing here to address a question that inevitably comes up whenever this story is discussed.
1:22:55
[SPEAKER_00]: Just how much actual violence are we talking about, across the purple gangs entire existence.
1:23:02
[SPEAKER_00]: You'll sometimes see figures circulating, in books, documentaries, and online articles,
1:23:09
[SPEAKER_00]: suggesting the gang was responsible for more than 500 killings during the bootleg wars of the 1920s and early 1930s.
1:23:18
[SPEAKER_00]: It's important in the interest of good history to treat that particular figure with real caution.
1:23:26
[SPEAKER_00]: Most serious historians who have studied the purple gang in depth regard the 5 to 100 number of
1:23:33
[SPEAKER_00]: as almost certainly an exaggeration, a figure that's essentially impossible to verify, given the incomplete, and sometimes deliberately falsified record keeping of the period, and one that may have originated more from sensationalised period journalism.
1:23:52
[SPEAKER_00]: than from any careful accounting.
1:23:55
[SPEAKER_00]: What is well documented through court records, contemporary newspaper coverage, and the research of dedicated historians, is a smaller but still substantial and genuinely disturbing list of specific, confirmed killings.
1:24:12
[SPEAKER_00]: The Milaflores Massacre of 1927, the murders connected to the cleaners and diers wall.
1:24:19
[SPEAKER_00]: the Collingwood Manomassica of 1931, and the string of individual killings and disappearances that marked the gang's slow disintegration through the 1930s.
1:24:32
[SPEAKER_00]: That's a smaller number than 500, certainly.
1:24:36
[SPEAKER_00]: But it's still a genuinely brutal record for any criminal organization to have compiled within roughly a decade and a half of activity.
1:24:45
[SPEAKER_00]: There's one other rumor worth addressing directly, simply because it comes up so often in popular retellings of this story.
1:24:53
[SPEAKER_00]: The Purple Gang has, for decades, been informally connected in the popular imagination to Chicago's infamous St. Valentine's Day massacre of February 14, 1929, in which seven men associated with Bugs Moran's north side gang were gunned down, reportedly on Al Capone's orders.
1:25:15
[SPEAKER_00]: The connection isn't entirely without basis.
1:25:19
[SPEAKER_00]: Some of the men suspected of involvement in planning or facilitating the St. Valentine's Day killing, including Fred Killerberg, the same man who had earlier helped carry out the Milaflora's massacre on the Purple Gang's behalf back in 1927, did have documented connections
1:25:43
[SPEAKER_00]: to the purple gangs broader network.
1:25:47
[SPEAKER_00]: Some accounts, even suggest, that a truckload of purple gang whiskey, hijacked by Bugs Moran's organization, may have been part of the underlying grievance that motivated Capone's retaliation in Chicago in the first place.
1:26:04
[SPEAKER_00]: But it's important to be precise here.
1:26:08
[SPEAKER_00]: There is no solid historical evidence that purple gang members themselves directly participated,
1:26:15
[SPEAKER_00]: in carrying out the actual killings in that Chicago garage.
1:26:19
[SPEAKER_00]: Chicago police at the time did investigate a possible purple gang connection, but it was never proven and most serious historians today treat the relationship as at most, one of overlapping personnel and business dealings between Detroit and Chicago's underworlds.
1:26:39
[SPEAKER_00]: rather than direct purple gang involvement in that particular Chicago crime.
1:26:44
[SPEAKER_00]: Beyond the individual fates of its members, the purple gang left behind a curious and somewhat contradictory cultural legacy.
1:26:53
[SPEAKER_00]: One that says almost as much about mid-20th century American attitudes, as it does about the gang itself.
1:27:01
[SPEAKER_00]: Hollywood took an early interest in the story, though rarely told it accurately.
1:27:06
[SPEAKER_00]: A 1935 film titled Public Hero Number One drew loosely on Purple Gang adjacent material.
1:27:16
[SPEAKER_00]: A later film, released in 1959, and simply titled The Purple Gang,
1:27:29
[SPEAKER_00]: stripped out the Jewish identity of the gang's real life members, almost entirely, giving its characters generic Anglo names instead, a choice that reflects the broader discomfort mid-century American popular culture often had with openly portraying Jewish criminality on screen, even when, as in this case,
1:27:53
[SPEAKER_00]: The underlying history was well documented and widely known.
1:27:58
[SPEAKER_00]: The hard-boiled crime novelist Raymond Chandler referenced the purple gang directly in his classic detective novel, Farewell, My Lovely, a nod to just how widely recognized the gang's name had become in American popular culture by the middle of the 20th century.
1:28:23
[SPEAKER_00]: offered its own fictionalised account of the gang's exploits as well.
1:28:29
[SPEAKER_00]: And in perhaps the most surprising and enduring pop culture reference of all, a mention of the purple gang survived, lyric intact, in a song performed in the 1980 film The Blues Brothers.
1:28:45
[SPEAKER_00]: introducing an entirely new generation of moviegoers to the gang's name.
1:28:50
[SPEAKER_00]: Most of whom, likely had no idea they were hearing a reference to a very real, very violent chapter of Detroit history.
1:29:00
[SPEAKER_00]: For serious students of this period, two books in particular stand out as the definitive historical works on the subject.
1:29:08
[SPEAKER_00]: and a worth mentioning here for anyone whose curiosity has been sparked by tonight's story.
1:29:14
[SPEAKER_00]: Paul R. Cavieff's book, The Purple Gang, organised crime in Detroit, covering the years 1910 through 1945.
1:29:25
[SPEAKER_00]: and Gregory A. Fornier's book, The Illusive Purple Gang, Detroit's Koshanostra, both represent years of careful archival research into a criminal organization that despite its outsized historical impact.
1:29:43
[SPEAKER_00]: has often been given far less popular attention than its contemporaries in Chicago and New York.
1:29:50
[SPEAKER_00]: It's worth reflecting in these final minutes on why that relative historical obscurity exists at all.
1:29:58
[SPEAKER_00]: Given just how significant the purple gangs role in national prohibition era crime actually was.
1:30:06
[SPEAKER_00]: Part of the answer likely lies in simple geography and media attention.
1:30:12
[SPEAKER_00]: Chicago had Al Capone, a genuinely singular, larger than life figure, who dominated national newspaper coverage throughout the 1920s, in a way that no single purple gang leader ever quite managed.
1:30:28
[SPEAKER_00]: since the purple gangs genuinely decentralised multi-headed structure meant there was never one instantly recognizable face attached to the organisation the way there was in Chicago.
1:30:42
[SPEAKER_00]: New York had its own deeply mythologised organised crime history later amplified by decades of film and television.
1:30:49
[SPEAKER_00]: Detroit's story by comparison involving a shifting, loosely organised confederation of young men whose most dramatic single act of violence, the Collingwood Manomassica.
1:31:02
[SPEAKER_00]: targeted other criminals rather than law enforcement, or prominent public figures, simply never generated quite the same durable national mythology, despite controlling by some estimates, three quarters of the entire nation's illegal liquor supply.
1:31:20
[SPEAKER_00]: at the peak of its power.
1:31:22
[SPEAKER_00]: There's also a specifically Jewish American dimension to this relative historical obscurity that historians and cultural commentators have noted over the years.
1:31:34
[SPEAKER_00]: Unlike the deeply entrenched multi-generational mythology that grew up around Italian American organised crime reinforced by decades of enormously popular films and television, Jewish American organised crime figures of the prohibition era, despite playing an enormous and undeniable role in the criminal underworld of that period, in cities from New York to Detroit,
1:32:03
[SPEAKER_00]: were often written out of, or actively obscured within, the popular crime narratives that Hollywood and popular publishing eventually settled on.
1:32:15
[SPEAKER_00]: The 1959 film adaptation of the Purple Gang's own story deliberately erasing the Jewish identity of its real historical subjects.
1:32:24
[SPEAKER_00]: stands as a particularly striking example of that broader pattern.
1:32:30
[SPEAKER_00]: In recent decades, historians, along with institutions like the Detroit Historical Society, and organizations dedicated to preserving Jewish American history, have worked to restore a more complete and accurate account of this chapter.
1:32:47
[SPEAKER_00]: Recognizing the purple gang not as some marginal footnote, but as a genuinely central, historically significant organization, within the broader story of American prohibition.
1:33:01
[SPEAKER_00]: an American organised crime as a whole.
1:33:04
[SPEAKER_00]: If you were ever to visit Detroit today, you could still trace many of the physical locations connected to this story, though most have changed considerably or vanished entirely over the intervening century.
1:33:18
[SPEAKER_00]: The old neighborhood of Little Jerusalem, where the Bernstein brothers and their childhood associates first grew up, has been almost
1:33:31
[SPEAKER_00]: and much of its original housing stock long since cleared away by decades of urban renewal projects and highway construction.
1:33:41
[SPEAKER_00]: The Miller-Flora's apartments.
1:33:43
[SPEAKER_00]: site of the 1927 machine gun massacre.
1:33:47
[SPEAKER_00]: No longer exists, having been replaced by a parking structure serving half a hospital.
1:33:53
[SPEAKER_00]: The Collingwood Manor Apartments site of the 1931 massacre that finally broke the gang's power is gone as well.
1:34:02
[SPEAKER_00]: its formal occasion now an empty lot.
1:34:05
[SPEAKER_00]: The book Cadillac Hotel, where A Bernstein spent his final comfortable decades, still stands proudly in downtown Detroit, restored and reopened decades later, as the western book Cadillac, one of the relatively few physical touchstones from this entire story that a present day visitor could actually walk into today.
1:34:30
[SPEAKER_00]: and the Detroit River itself, of course, is still there.
1:34:35
[SPEAKER_00]: Still flowing quietly past the city, though it now carries commercial freighters and pleasure boats rather than smuggled Canadian whisky.
1:34:44
[SPEAKER_00]: It's once notorious half-mile crossing to Windsor, now spanned by the enormous, entirely legal traffic of the Ambassador Bridge.
1:34:54
[SPEAKER_00]: So what should we take away from this story as we settle in towards sleep tonight?
1:35:00
[SPEAKER_00]: Perhaps this, that the purple gangs rise and fall is, in many ways, a distinctly American story, shaped by immigration, by poverty, by a strange and short-lived national experiment in outlawing something an enormous portion of the public still wanted badly enough to fund an
1:35:24
[SPEAKER_00]: It's a story about how geography itself, a narrow half-mile stretch of river between two countries with two very different sets of laws, can shape the fortunes of an entire city and an entire criminal organization.
1:35:40
[SPEAKER_00]: And it's a story, too, about the particular fragility of power built on fear and loose loyalty, rather than genuine structure and discipline, an organisation that could seize astonishing wealth and influence in a remarkably short span of years, and then lose nearly all of it just as quickly, undone as much by its own internal betrayals as by any external enemy.
1:36:12
[SPEAKER_00]: If tonight's story kept you company the way it was meant to, and you'd like to spend more evenings like this one with us here at Sleepless History, following some other quiet half forgotten corner of the past, please do take just a moment before you go to leave a comment, letting us know you were here tonight, and to follow or subscribe if you haven't already, so that future episodes find you automatically,
1:36:42
[SPEAKER_00]: It genuinely helps this small show keep finding its way to people who need exactly this kind of company at the end of a long day.
1:36:52
[SPEAKER_00]: Thank you sincerely for spending this stretch of your evening with me.
1:36:58
[SPEAKER_00]: I'll see you again next time.
1:37:00
[SPEAKER_00]: Good night.