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Top 10 Scariest Chicago Serial Killers · Murder Files Unsealed

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  Speaker 1: Welcome back everyone. Get ready for a deep dive today, folks. Chicago, right,
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  a city known for its skyline, it's pizza, its energy, right,
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  But beneath that vibrant surface, there's a history, a dark history. Yeah,
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  we're talking about serial killers.
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  Speaker 2: It's true, and we're going deep, folks. We've got this
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  compilation of cases really shines a light on Chicago's dark side.
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  Speaker 1: And the thing is, right off the bat, this isn't
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  your typical serial killer trope, not at all.
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  Speaker 2: You've got these individuals seemingly normal integrated into Chicago society.
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  Some well, let's just say, their past would raise a
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  few eyebrows if anyone knew.
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  Speaker 1: Hiding in plain sight as they say, exactly, which is
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  I mean John Wayne Casey, right, contractor by day Pogo,
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  the clown for the kids on weekends. Yeah, just think
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  about that, the trust, the access, and.
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  Speaker 2: How that case sadly really changed how people see clowns forever,
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  that friendly persona. The whole point was to disarm people. Appearances, Man,
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  they can be deceiving.
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  Speaker 1: Deceptive is one word for it. Yeah, then you've got
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  hh Holmes, Yeah, talk about next level, Oh Holmes. This
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  guy builds a hotel, right for the World's Fair, secret rooms,
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  passages like some kind of death trap labyrinth. It's true,
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  who thinks like that?
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  Speaker 2: And that's where the psychology gets really really interesting, really complex,
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  no easy answers. Right, but Holmes he's all about control,
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  exerting power over his victims, but in this really calculated,
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  meticulous way.
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  Speaker 1: Okay, but that's what throws me. If Holmes is about control,
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  what about Gaycy. He's got the clown act, the manipulation.
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  What's the motivation there?
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  Speaker 2: See, that's the question, isn't it the why? With Gaycy?
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  Maybe it was the thrill of the khn the power
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  of deception. Remember, we're talking about a complex mix of
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  factors here, upbringing personality, even how society plays a.
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  Speaker 1: Role, Does nature and nurture all tangled up in this
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  really messed up way?
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  Speaker 2: Exactly? Each killer' psyche is its own messed up puzzle.
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  Speaker 1: And speaking of messed up, the source material mentions this
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  group the Ripper Crew, operated in Chicago in the eighties.
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  Satanic rituals, brutal murders. They took things to another level.
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  Speaker 2: Oh, absolutely, the Ripper Crew, with the rituals and well
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  everything else. It points to sadism. A need to dominate,
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  not just in life, but even after death. It shows
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  you how someone's fantasies, their inner world can become this
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  terrifying reality.
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  Speaker 1: It makes you wonder how someone even gets to that point.
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  Like Richard Speck, he's in the navy, right, gets discharged,
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  then goes on a rampage in a nurse's dorm, just
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  pure rage.
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  Speaker 2: And that's where we have to look at the role
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  of fantasy, particularly with Speck. It seems like this rage
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  may be directed at women, maybe rooted in past experiences.
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  It just exploded.
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  Speaker 1: So what we're seeing here, it's not one size fits all. Right,
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  there's no single answer to why someone becomes a serial killer.
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  Speaker 2: Now, each case it's its own recipe of horror, with
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  its own terrible ingredients.
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  Speaker 1: And believe me, this compilation we're just getting started. It's
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  heavy stuff, no doubt. Yeah, and it makes you think. Right,
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  we analyze, we look for patterns, but how do you
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  really grasp that kind of darkness?
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  Speaker 2: You really can't. And that's something important to remember as
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  we go through these cases. These aren't just stories. We're
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  talking about real victims, real families torn apart.
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  Speaker 1: It's easy to get caught up in the I don't
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  know the macaw fascination of it all, but the human
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  cost that's what sticks with you.
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  Speaker 2: Absolutely.
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  Speaker 1: And speaking of human costs, this William Aaron's case, the
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  Lipstick killer back in the forties. That one really gets
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  to me.
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  Speaker 2: Right, the messages he left in Lipstick. Imagine the investigator
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  seeing that adds a whole other dimension to his psychology,
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  Like he wanted to taunt them.
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  Speaker 1: It's like he almost wanted to get caught. But before
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  we go too far down that rabbit hole, you mentioned
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  criminal profiling earlier, What exactly is that? How does it work?
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  Speaker 2: So criminal profiling it's a tool law enforcement uses. They
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  try to predict the characteristics of an unknown offender based
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  on the crime scene, the victims. How they operate all
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  of it to sort of paint a psychological portrait, so
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  to speak.
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  Speaker 1: So basically trying to get inside the mind of a
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  killer in a way.
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  Speaker 2: Yes, but it's not an exact science, not by all
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  long shot. More like informed guesswork with a lot of
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  ethical questions tied in how so well take Errand's he
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  was just a teenager, right, no question he did it.
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  But were his mental vulnerabilities really considered.
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  Speaker 1: Back then, that's a heavy thought. But then you have
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  these cases less about instability, more about cold calculation. Leopold
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  and Lobe come to mind.
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  Speaker 2: Ah, Leopold and Lobe the perfect example of well intellectual
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  arrogance gone wrong. Two privileged students University of Chicago. They
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  thought they could commit the perfect crime and.
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  Speaker 1: They targeted Who was it again.
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  Speaker 2: Bobby Franks, just fourteen years old, just a kid. They
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  killed him to prove a point that they were smarter
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  than everyone else.
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  Speaker 1: The arrogance is mind blowing. Talk about human cost. A
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  young life just snuffed out, a family destroyed because these
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  two guys playing god.
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  Speaker 2: And that's what makes the case so chilling. The lack
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  of remorse. It was all a game to them, an
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  intellectual exercise. That kind of detachment. It's often linked.
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  Speaker 1: To psychopathy, psychopathy, we hear that term.
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  Speaker 2: What is it really so psychopathy? It's not just about
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  being violent or cruel, though those can be part of it.
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  It's deeper. It's a lack of empathy, no remorse, no guilt.
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  People with these straits they have trouble forming real emotional connections,
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  so like emotionally detached exactly, and they can be incredibly manipulative,
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  very good at blending in so.
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  Speaker 1: Leopold and Low with their planning, the lack of remorse.
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  That could be a psychopathic profile.
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  Speaker 2: Potentially, yes, And that's a key point. Psychopathy isn't always
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  in your face. It can be hidden, even charming, like a.
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  Speaker 1: Wolf in sheep's clothing. So I've got control, power, ambition,
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  and now psychopathy. It's a recipe for disaster.
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  Speaker 2: It is. And in a city like Chicago, with its history,
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  other factors come into play as well.
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  Speaker 1: You can't talk about Chicago's dark side without mentioning organized
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  Crimeshio al Capone, the Saint Valentine's Day massacre, seven people
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  gunned down just like that. It wasn't just about eliminating rivals.
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  It was a.
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  Speaker 2: Spectacle, Oh absolutely, it was a message. This is what
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  happens when you cross off Pone. But you see with Capone,
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  with organized crime, it's a different breed. It's not the
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  same psychology as a gacy or a homes.
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  Speaker 1: Right, different motives, different monsters, exactly.
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  Speaker 2: With Capone, it's about power, control of the city, the money,
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  the whole game. But what's interesting you even see darkness
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  emerge within families.
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  Speaker 1: Closer to home. And me.
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  Speaker 2: Right, take Patricia Columbo and Frank de Luca nineteen seventy six.
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  They killed her family, her own parents and brother.
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  Speaker 1: Wow, just wow, What could possibly drive someone to do that?
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  Speaker 2: Well, the motive seems to be a mix of things.
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  A bad relationship, resentment towards the family, and money was involved.
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  Speaker 1: To still, to kill your own flesh and blood, that's cold.
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  She was just a kid herself, wasn't she eighteen?
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  Speaker 2: And that's what makes it so complicated. Was she manipulative
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  or was she a victim of De Luca's influence. It's
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  still debated today, so.
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  Speaker 1: Many layers to these cases. It's like you never really
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  know the whole story, but it reminds you evil can
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  be anywhere, even in your own family.
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  Speaker 2: Absolutely, and sometimes it on the most vulnerable among us.
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  Speaker 1: That's what gets me about this Andre Crawford case. Years
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  he terrorized the Englewood neighborhood.
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  Speaker 2: Yeah, Crawford's case, it's heartbreaking. He targeted women, many struggling
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  with addiction, women who were often overlooked, forgotten, so he.
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  Speaker 1: Took advantage of their situation, their vulnerability.
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  Speaker 2: It's a tragic example of how societal issues, poverty, addiction,
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  they can create an environment where this kind of darkness
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  can thrive.
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  Speaker 1: So it's not just about catching the monsters, it's about
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  preventing them in the first place.
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  Speaker 2: Right, And that's where the justice system it has to
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  walk a fine line.
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  Speaker 1: Speaking of which, this Justseph Miller case. Talk about a
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  punch to the gut, get paroled after killing two women.
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  Then he picks up right where he left off.
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  Speaker 2: Miller's case really exposes the challenges of rehabilitation. How do
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  you fix someone like that? Can you even call it fixing?
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  Speaker 1: It's like, what do you even start.
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  Speaker 2: It's a question that haunts the entire system, and frankly
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  it should because these aren't just abstract cases. These are
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  real lives, forever change now.
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  Speaker 1: We can't forget that. So as we wrap up this
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  deep dive, I guess the question is where do we
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  go from here?
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  Speaker 2: Well, for me, it always comes back to understanding. The
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  more we learn about these dark corners of human behavior,
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  the better prepared we are.
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  Speaker 1: To confront them. So knowledge is power.
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  Speaker 2: Exactly, and it's our best defense against the darkness.
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  Speaker 1: Well said, Well, folks, there you have it, a glimpse
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  into the shadows of the windy city. Keep asking questions,
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  keep learning, and most importantly, keep yourself safe until next time.