Latest / Reformed Thinking / Serpents in Sacred Robes: Christ’s Woe Against Hypocritical Religion (Matthew 23:29-33)

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Serpents in Sacred Robes: Christ’s Woe Against Hypocritical Religion (Matthew 23:29-33) · Reformed Thinking

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Modern culture loves to paint Jesus as a well as a mild
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mannered life coach. Yeah, that is very common.
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A pacifist handing out quiet affirmation to everyone he
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meets. But turn to the final days of
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his life in the New Testament, and that soft, therapeutic
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portrait shatters. You do not find a harmless
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philosopher. No, you really don't.
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You find the lion of the tribe of Judah staring down the most
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influential religious elite of his day, looking them in the eye
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and telling them they're venomous snakes headed for the
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eternal fires of a garbage dump. It is a striking image.
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Welcome to Reformed thinking. I'm glad you're joining us.
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Today we are looking at Matthew 23, verses 29 through 33.
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We are working through 2 rigorous textual commentaries
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today. The 1st is called Serpents in
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Sacred Roves and the second is the terrifying reality of divine
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judgement. Both sources focus on the 7th
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and final woe Jesus pronounces against the scribes and the
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Pharisees. Right, the 7th woe.
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And this text exposes A terrifying tendency of the human
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heart, the instinct to honor dead Saints and build monuments
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to past heroes, all while harboring A vicious hostility
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toward living truth. Consider your own position for a
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moment. Have you ever considered that
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the most dangerous place a person can be might not be in a
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den of iniquity, but sitting comfortably in a religious
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setting, trusting in their own moral achievements?
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That tension, that specific contradiction, is the central
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mechanism of this passage. To grasp the sheer force of
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Christ's rebuke here, we have to look at the physical and socio
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political setting of 1st century Judea.
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Because he's not just saying this in a vacuum.
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No, not at all. Jesus is standing in the temple
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precincts in Jerusalem, and this is during Passion Week, so the
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political atmosphere is incredibly volatile.
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But the geographical backdrop that provides the immediate
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context for his words. Just outside the city walls,
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down in the Kidron Valley, stood these elaborate, highly ornate
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tombs and monuments. OK, so these are right nearby.
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Yes, and these structures were dedicated to Old Testament
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prophets like Zechariah. And we should clarify, these
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were not modest headstones. We were talking about massive
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towering architectural achievements.
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Oh, they were stunning, Yeah. Very grand.
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And in that specific cultural moment, funding the restoration
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and beautification of those tombs was considered the highest
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form of public virtue signaling for the wealthy religious elite.
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So as a status symbol. Yes, a massive 1.
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The scribes and Pharisees would pour vast sums of money into
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polishing the marble, expanding the sepulchers, adding these
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ornate carvings. It was a highly visible method
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of broadcasting their supposed piety to the masses.
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The underlying message of the architecture was essentially
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look at how much we Revere the Word of God and look at how much
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we honor the prophets who brought it to our ancestors.
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I think we have a massive historical blind spot regarding
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the Pharisees. Today the word Pharisee
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functions as a synonym for a hypocrite or a villain.
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We picture them as these cartoon antagonist, you know.
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Yeah, the bad guys in the story. Right, but the general populace
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in the 1st century viewed them entirely differently.
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They were the good guys. They were the defenders of
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orthodoxy. The common people absolutely
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Revere them, and to understand why, you have to trace their
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spiritual lineage back to the intertestamental period, back to
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a group called the Hasidim. The pious ones.
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Yes, the pious ones. During the reign of the Selustan
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Empire, there was this tyrant named Antiochus Epiphanes, and
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he attempted to force Hellenization on the Jewish
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people. He outlawed circumcision.
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He burned copies of the Torah it.
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Was brutal suppression. Very brutal.
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And he infamously sacrificed a pig on the altar in Jerusalem.
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Which is just the ultimate desecration for a Jewish person.
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Unthinkable now, many within the nation capitulated to save their
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own lives. But the Hasidim?
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They were the heroes who resisted.
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They held the line. They were willing to be tortured
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rather than violate the law of. God, so they possessed this
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incredible historical pedigree. They were the uncompromising
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stalwarts of the faith who survived the fire.
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And that historical pedigree granted them massive cultural
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capital. By the time of Christ, the
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descendants of that movement had evolved into the Pharisees, this
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powerful sect defined by rigorous microscopic adherence
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to the Law. The people view them as the
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anchor holding the nation together.
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OK, so setting that scene makes Christ's words hit so much
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harder. It does so when Jesus stands in
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the terrible courtyard and publicly calls these respected,
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beloved leaders hypocrites and Vipers.
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The shock value is well, it's difficult for us to comprehend
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today. It was a socially scandalous,
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religiously explosive indictment.
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It reminds me of politicians or wealthy donors today who fund
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massive bronze statues of civil rights leaders or historical
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reformers. They cut the ribbon, they stand
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in front of the cameras, and they bask in the applause.
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They are virtue signaling with marble.
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That is a great comparison. They use the monument to project
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an image of righteousness to the public, but the physical action
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of building a beautiful tomb is a brilliantly crafted cover for
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a sinister internal reality. The outward display is a mask.
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And the vocabulary Jesus uses strips that mask away
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completely. He begins the sentence with the
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word whoa. Just a single word, but it
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carries so much weight. It does.
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The commentaries provide a strict linguistic breakdown of
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the Greek word used here, which is why it is an onomatopoic
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prophetic formula. Wait.
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Unpack that for us Onomatopoic. It sounds like what it means.
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It is not an exclamation of sorrow like someone sighing.
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It is a formal declaration of impending doom and divine
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judgment. Because we often read it like a
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sigh, like Jesus is just disappointed in them woe is me
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kind of thing. Yeah, that's a common
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misconception, but he is drawing this directly from the Old
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Testament prophets. Isaiah and Jeremiah use similar
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language to pronounce covenantal curses upon a rebellious nation.
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When Jesus says why, he's operating as the divine judge,
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bringing a gavel down on the bench.
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He is pronouncing a sentence. Yes, and he follows that
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judicial strike by identifying them as hypocrites.
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That is another word that has lost its edge.
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In modern English, we call someone a hypocrite if they tell
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us to limit our screen time while they scroll on their
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phone. The Greek concept carries far
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more weight, doesn't it? Much more, the term is
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hippocrati. Its origin lies in the Greco
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Roman Theatre. A hypocrites was a play actor in
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classical drama. These actors wore large
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exaggerated masks to conceal their true identity and project
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a different character to the audience.
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So they were literally wearing masks?
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Literally. And the mask had a small
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megaphone built into the mouthpiece to project the voice.
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Jesus is identifying the Pharisees as spiritual play
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actors. They wear the mask of pristine
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piety, covering themselves in the phylacteries of the law,
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performing all the correct rituals.
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Yet underneath that mask, their hearts remain entirely
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unregenerate. The specific scene they're
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acting out is this grand public display of honoring dead
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prophets. But the sources point out the
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glaring, grotesque contradiction here.
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These leaders are painstakingly decorating the monuments of dead
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prophets in the valley, while at the exact same moment they are
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actively conspiring to murder the of God in the city.
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It's staggering. And that contradiction exposes
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the core psychology of their religion.
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They love the dead prophets because, well, dead prophets are
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safely silenced. They can't talk back, right?
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A prophet from a bygone era cannot look you in the eye and
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rebuke your current act of sins. Their fiery sermons can be
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domesticated, managed, and turned into safe, comfortable
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traditions. Human nature always prefers the
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silent framed quotes of historical figures over a living
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authority demanding submission. Right now, a dead prophet asks
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nothing of you. A living 1 demands repentance.
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That is so true. We love to take a false,
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uncompromising historical figure, put their quote on a
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coffee mug and pretend we would have marched right beside them.
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Meanwhile, if that person were standing in our living room
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calling out our actual behavior, we would throw them out of the
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house. We want the aesthetic of the
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prophet without the conviction of the prophecy.
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And that psychological reality leads the Pharisees to make a
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highly specific arrogant boast in verse 30.
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They claim if we had lived in the days of our fathers, we
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would not have taken part with them in shedding the blood of
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the prophets. On the surface, it sounds like a
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noble disavowal of past atrocities.
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They are condemning the sins of their ancestors.
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It sounds like the right thing to say, doesn't it?
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They are distancing themselves from the murderers, but the
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grammatical structure betrays them.
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In the original Greek, this is a second class conditional
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sentence. OK, take us back to grammar
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class. What does a second class
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conditional sentence mean here? That specific syntax implies a
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condition contrary to fact. They are creating a hypothetical
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historical scenario where they insert themselves into the
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narrative and they assume they possess the inherent moral
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fortitude to make a righteous choice.
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They are saying we are structurally different from our
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ancestors. We are better.
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Yes, that boast reveals a massive theological error.
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By claiming they would have inherently chosen the righteous
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path, they are denying the doctrine of total depravity.
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Oh wow, so this goes right to the core of human nature.
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It does. They are operating on the
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assumption that human beings possess a core of inherent
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goodness and untainted free will, capable of choosing
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righteousness if just given the right circumstances.
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The commentaries know this is the seed of Pelegian thought,
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trusting in human moral capability rather than
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recognizing that the human heart is fundamentally corrupted by
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original sin. It is the ultimate form of
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historical Monday morning quarterbacking.
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Yes, that's a perfect way to describe.
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It it is so easy to sit in a comfortable chair, read a
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history book about massive societal atrocities, and assume
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you would be the lone dissenter hiding the refugees or standing
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up to the tyrant. You look at the past and say I
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would never have done that. Jesus identifies this historical
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hindsight as a symptom of total moral blindness.
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You think you are superior, but you share the exact same corrupt
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nature. And Jesus hears this boast and
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weaponizes their own words against them in the courtroom of
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God. He turns their defense into the
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evidence that will secure their conviction.
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I noticed a specific hinge in the Greek text that shifts the
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focus from their boast to their condemnation.
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It is a subtle pivot in the language.
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The pivot rests on a single word in verse 31.
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It is the Greek resultative conjunction host which
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translates as therefore or so that the commentators identify
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this as the structural hinge of the entire passage.
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Up until this word, Jesus has been describing their actions
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and quoting their hypothetical boast.
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Setting up the scene right. But with the arrival of HOST,
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the atmosphere transforms into a formal legal proceeding.
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He is submitting their statement into the official court record.
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Jesus says, therefore you witness against yourselves that
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you are sons of those who murdered the prophets.
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By claiming if we had lived in the days of our fathers, they
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voluntarily admit biological descent.
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They claim the Father's physically to elevate their own
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status, even while attempting to distance themselves morally.
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But Jesus supplies a completely different meaning to the word
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sons. He is not talking about their
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DNA. In biblical literature, being a
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son of someone frequently implies characterological
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likeness. You share the nature, the
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desires, and the behavioral patterns of your father.
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The commentaries refer to this as spiritual cloning.
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Spiritual cloning. I like that phrase.
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The Pharisees are spiritual clones of the murderers they
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claim to despise. They share the identical
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hostility toward the divine message, the Father's murdered
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Isaiah. The sons are currently plotting
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to murder Jesus. The outward religious expression
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has changed, but the internal unregenerate nature remains
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untouched. God does not just judge actions,
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He judges speech. The words we use to justify our
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own righteousness become the transcript at our own trial.
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Consider how this applies to our current cultural climate.
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The loudest critics of historical atrocities are
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frequently the ones most blind to their own identical hostile
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impulses today. That is a very sobering thought.
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We loudly condemn the intolerance of previous
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generations, completely unaware of the ruthless, venomous
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intolerance we display toward anyone who disagrees with us in
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the present. We use our condemnation of the
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past to mask our complicity in the present.
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And because they share this murderous nature, Jesus issues a
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command to them in verse 32 that is incredibly difficult to
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process. He says fill up then the measure
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of your Father's. I really struggle with that
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verse. Fill up the measure.
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At first glance that sounds like Jesus is commanding them to sin,
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like he is actively pushing them to commit murder.
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How do the sources reconcile that with a God who does not
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tempt anyone to evil? The sources provide a rigorous
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grammatical and theological defense.
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Here the command to fill up translates from the Greek
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heiress imperative pleurisate. The commentators clarify that
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this is not an enticement to evil, it is a decree of judicial
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hardening. Judicial hardening.
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Right. The imagery involves a measuring
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cup of accumulated generational guilt.
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God is exceptionally patient, but his patience has a wholly
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fixed limit. He has watched generations of
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Israel reject the prophets, beat the messengers, and shed
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righteous blood with every single act of rebellion.
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Drops of guilt fell into this measuring cup.
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God allowed space for repentance, but that space is
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not infinite. So the cup is practically
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overflowing by this point. The climax of national rebellion
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has arrived. The nation is preparing to top
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off the cup of iniquity by crucifying the Incarnate
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Messiah. The Father's killed the
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servants. The sons are preparing to kill
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the Son. When Jesus issues the
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imperative, fill up the measure. He is enacting A judicial
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handing over. He is saying you are hardened in
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your rebellion. You refuse to repent.
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So complete the wicked work your ancestor started.
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Let the fullness of your guilt be realized.
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It functions like a generational credit card with a massive
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limit. They have been charging acts of
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rebellion against God for centuries.
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Every murdered prophet, every ignored warning, every act of
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idolatry gets added to the balance.
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God has deferred the payment, but Jesus is standing in the
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temple effectively saying run the card one last time, Max it
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out on me. The bill is due today.
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That is exactly what is happening.
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Then the completion of that generational guilt triggers a
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terrifying eternal sentence. The bill coming due means the
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judgement has fallen, and the language Jesus uses to deliver
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this sentence represents some of the most aggressive, unvarnished
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vocabulary in all the Scripture. We see the tension peak in verse
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33. Jesus looks at these esteemed,
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respectable men, at theological conservatives of the nation and
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says, you serpents, you brood of Vipers, how are you to escape
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being sentenced to hell? The sources examine the Greek
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terms ophis meaning serpents, and Ginamata kidnan meaning
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brood of Vipers. This is not a sudden loss of
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temper. Jesus is not simply throwing
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insults. Right.
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He is not just calling them names, no.
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This is a highly calculated theological indictment.
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It is a direct invocation of Genesis 3.15, the proto
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evangelium, where God declares perpetual war between the seed
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of the woman and the seed of the serpent.
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The Pharisees based their entire identity and security on being
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the children of Abraham. That was their ultimate boast,
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yet Christ identifies them as the spiritual seed of the devil.
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They are venomous, deceptive, and fundamentally opposed to
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God's redemptive plan. After identifying their true
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spiritual lineage, Jesus brings up the sentence of hell.
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The Greek word used here is jina.
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The sources provide a critical historical breakdown of this
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term deriving from the Valley of Hinnom, a ravine located just
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South of Jerusalem. The historical reality of that
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valley is incredibly dark. It was not just a geographic
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location. Far from it.
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It was the site of the most grotesque idolatry in Israel's
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history. During the reigns of apostate
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kings like Ahaz and Manasseh, Israelites participated in
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Canaanite child sacrifices in this valley.
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Child sacrifices right outside the Holy City.
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Yes, they built high places to the false God Molech and burned
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their own children in the fire. Decades later, King Josiah
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enacted sweeping, righteous reforms to stop the idolatry.
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He intentionally desecrated the valley.
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He smashed the altars to file the ground and turn the entire
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ravine into a smoldering, perpetually burning garbage dump
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for the city of Jerusalem. So it became a literal
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wasteland. Dead animals refuse and the
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unburied bodies of criminals were thrown into the fires there
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so. The fires are literally always
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burning to consume the waste. By the 1st century, this
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gruesome, visceral imagery had become the standard Jewish idiom
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for the place of final, eternal, conscious punishment for the
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wicked. When Jesus asks how are you to
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escape being sentenced to hell, he's invoking the most
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terrifying image of judgement available in their cultural
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vocabulary. The syntax of his question
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expects a specific answer, doesn't it?
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He is not asking for their escape plan.
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The Greek phrasing post Fugan expects a negative answer.
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Evasion is impossible. You cannot escape the justice of
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God by building tombs, by quoting dead prophets, or by
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accumulating external moral achievements.
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That raises a massive question about the modern theological
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landscape. There is a strong, pervasive
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aversion to the concept of hell today.
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Many want a version of Jesus who functions as a harmless moral
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philosopher, someone who offers peace but never threatens
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judgement. If Jesus spoke so aggressively
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and clearly about Gehenna, why does modern theology try to
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erase it? The commentaries address this
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directly. When you remove the wrath of
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God, you get the gospel. The biblical Jesus strips away
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all of our self righteousness and exposes our desperate,
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corrupt condition. The severe judgement we see in
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Matthew 23 is not an isolated incident.
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The sources highlight that this passage marks a massive
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dispensational shift to the redemptive historical storyline
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of the Bible. Let us unpack that literary
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context. Where does the specific woe fit
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into the larger narrative architecture of Matthew's
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Gospel? This is the 7th and final woe.
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It marks the tragic, definitive end of Christ's public appeal to
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national Israel. He is permanently closing the
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door on His public ministry to the religious leaders.
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It's the end of an era. It truly is.
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Immediately following this row, Jesus utters his famous lament
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over Jerusalem, declaring their house desolate.
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He then physically departs from the temple complex.
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He walks away and that action sets up the events of the next
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chapter. His departure sets the stage for
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the Olivet Discourse in Matthew 24, where he outlines the future
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destruction of the Temple and the end of the age.
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Israel's leaders are apostate, the offer of the Kingdom has
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been rejected, and a new era in God's redemptive plan is
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beginning. The commentary spend significant
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time dealing with the theological harmony between
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divine sovereignty and human responsibility.
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In this moment, the religious leaders are making real choices,
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but God is not reacting to a sudden change of plans.
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The commentators laid out a robust defense of compatibilism.
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The crucifixion is approaching. It represents the ultimate crime
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of human depravity. The Pharisees are acting freely,
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maliciously, and wickedly. They are fully responsible for
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their venomous hatred of the Messiah.
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They aren't robots. Right.
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They are choosing this, yet simultaneously their wicked
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actions are unfolding perfectly within God's sovereign, eternal
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decree to secure redemption for His elect.
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They are filling up the measure of their Father's guilt by their
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own volition, but God is utilizing their rebellion to
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accomplish the atonement. The sources offer a sharp
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critique of liberal theological frameworks.
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They argue that any theology attempting to domesticate Jesus,
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removing the concept of divine wrath to make him palatable to
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modern sensibilities, fundamentally distorts the text.
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And we're reporting this objectively to show how these
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rigorous commentaries view the landscape, They insist you
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cannot separate the loving, healing Jesus from the
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terrifying judging Jesus. The tension is baked into the
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inspired narrative. The text refuses to allow us to
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soften the blow. There is a, well, a very dark
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irony in the narrative. The religious leaders operate
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under the delusion that they are in control.
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They believe they are eliminating a political nuisance
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to protect their establishment, but in reality they're playing
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the exact roles written for them in a divine script they refuse
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to read. They think they are the
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directors of the play, but they are just characters fulfilling A
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prophecy they claim to understand.
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If this severe, unvarnished judgement fell upon the most
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respected scripturally literate religious elite of the 1st
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century, it forces us to ask a difficult question.
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What are the implications for the Church today?
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We have to hold this text up as a mirror.
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We cannot leave this conflict safely locked away in the 1st
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century. The commentaries provide some
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very direct piercing applications to expose modern
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hypocrisy. They start by critiquing
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external institutional systems. The text acts as a polemic
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against any religious framework relying on outward works
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righteousness. For instance, the sources draw a
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direct parallel between the Pharisees decorating the tombs
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of the prophets and the Roman Catholic veneration of relics.
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That makes a lot of sense. The physical acts of devotion,
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the ornate cathedrals, the preservation of Saints bones,
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these practices mask a fundamental reliance on human
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effort rather than the finished sufficient work of Christ.
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It is easy for Protestants to nod along with that critique,
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but the commentators do not let evangelicalism off the hook, do
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they? Not at all.
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They point their critique at prosperity gospel movements and
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seeker sensitive mega churches. These organizations build
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massive physical empires based on carnal success, emotional
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metrics and crowd appeal. They construct beautiful modern
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tombs with state-of-the-art lighting and sound while
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completely ignoring the biblical demands for repentance, the
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reality of total depravity, and the terrifying truth of God's
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wrath. But I want to push this even
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closer to home. It is incredibly easy for
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someone with a robust reformed theological framework to throw
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stones at the flashy mega church down the street and spot all
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their superficial flaws. Very true.
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But what about the person sitting in a confessional,
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conservative church? The person who possesses the
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most pristine, accurate, systematic theology on paper
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they can call Calvin. They have read all of Spurgeon,
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they hold all the correct doctrines, yet they treat their
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family with cruelty, they slander their Co workers, and
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they exhibit total contempt for anyone who lacks their
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intellectual rigor. Isn't dead cold orthodoxy just a
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very well painted, highly intellectual tomb?
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That is the most devastating application of the text.
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Intellectual assent to correct doctrine does not equal a
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circumcised heart. The Pharisees possess the most
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precise scriptural knowledge of anyone in Jerusalem.
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They memorized the Porah, yet Jesus looked at them and called
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them a brood of Vipers. Because the knowledge didn't
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change the heart. Right.
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You can possess A flawless theological pedigree, but if
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there is no fruit of the Spirit, no genuine humility, no love for
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the brethren, your theology is just a different genre of play
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acting. We have walked through an
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intensely heavy condemning text today.
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The hypocrisy of the human heart has been exposed, the arrogant
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boast of moral superiority dismantled and the inescapable
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judgement of Gehenna pronounced. If the deep dive stops here, it
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feels incredibly bleak. It does, but the commentators
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insist we cannot leave the text in despair.
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The very passage that condemns the hypocrite also points toward
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the only avenue of escape. The Gospel provides the
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resolution to the terror of Matthew 23.
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Let us look into that resolution.
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How does Christ offer an escape from the very wrath he just
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proclaimed? This is the glorious theological
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connection found in the sources. Jesus is the final ultimate
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prophet that the religious leaders killed.
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He is the culmination of all the righteous bloodshed on the
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earth. But he is not just another
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victim of human depravity. He is the righteous substitute.
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Walk us through the mechanics of that substitution.
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The text warns of the inescapable sentence of Gehenna.
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Total depravity means every single human being inherently
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deserves that exact sentence. How does the cross solve the
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problem of divine justice? On Calvary, the spotless Lamb of
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God stepped into the courtroom and voluntarily stood in the
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place of hypocrites, liars, and Vipers.
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God did not simply sweep our guilt under the rug.
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That would compromise His justice.
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He had to deal with the sin. Yes, instead Jesus absorbed the
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infinite, unmitigated wrath of Gehenna upon himself.
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He drank the cup of God's fury down to the absolute dregs,
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exhausting the penalties so that his elect might drink the cup of
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blessing. He took the punishment for the
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very hypocrisy he condemned in Matthew 23.
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The Pharisees spent their wealth building and decorating tombs
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for dead prophets. A few days after the speech,
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they put Jesus in a tomb, expecting him to stay there
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permanently. But the empty tomb of Christ
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stands in permanent, eternal victory over the decorated tombs
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of the dead prophets in the Kidron Valley.
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He conquered the death that they memorialized.
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That reality changes our entire standing before God.
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It moves us from the terror of imminent judgment to the relief
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of unmerited grace. As we wrap up this session, I
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want to leave you with a final thought to Mull over.
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We spent a lot of time talking about the Pharisees building
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marble monuments in the 1st century.
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But consider the monuments we build today.
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We live in a digital age where we construct highly curated
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online avatars. We build digital tombs on social
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media. We post quotes from revered dead
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theologians to signal our own virtue and theological precision
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to our followers. Yet in the comment sections, we
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bite and devour living believers with venomous hostility.
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We use the words of dead Saints to mask our own unregenerate
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behavior in the present. If Jesus Christ were to evaluate
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the digital monuments you have built in your own life, your
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online reputation, your theological persona, your
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carefully crafted image would keep him.
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Here he find a living, breathing faith marked by humility and
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repentance. Or just a beautifully decorated
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digital tomb. Stop trusting the monuments you
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build and start trusting the Messiah who was crucified for
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your hypocrisy. A vital piercing question for
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anyone who claimed to know the truth.
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Thank you for joining this deep dive into the text.
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Open up Matthew Chapter 23, read it with fresh eyes, and let the
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text drive you to the cross. Until next time.