WEBVTT

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Imagine a man sitting in a maximum security prison

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cell. Okay. He is currently serving four consecutive

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life sentences, plus an additional 110 years.

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Which is just a mathematically staggering amount

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of time. Right. The federal government's basically

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done everything in its power to permanently erase

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this guy from society. Yeah. Legally speaking,

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he's a ghost. Exactly. But now I want you to

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imagine that this same man is simultaneously

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charting on Spotify algorithms. Oh. Wow. His

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voice is touring the globe right now, reaching

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millions of listeners on a 2024 hip hop album.

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It really defies all logic. It totally does.

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Welcome to today's Deam Dive. We are taking the

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source material on a man named Donald Green,

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though he's much better known to the streets

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and the culture as Sly Green. Right, Sly Green.

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And we're unpacking a story of massive ambition.

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wild hubris, and a modern day cultural afterlife

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that completely breaks the standard biographical

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mold. It's the absolute definition of a history

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that, you know, just refuses to stay in the past.

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We're looking at a highly ambitious American

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drug trafficker, a gangster, and the founder

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of the notorious L .A. Boys Gang in Buffalo,

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New York. Right out of Buffalo. Yeah. And the

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sheer scale of this story, both financially and

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psychologically, is what makes it such a compelling

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case study. So our mission today is to figure

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out exactly how a local Buffalo kingpin built

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an empire. with a $50 million vision. A massive

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vision. Yeah. And then we'll look at the unbelievable

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audacity that led to his downfall and somehow

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how he managed to remain this prominent voice

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in culture decades after the cell door locked.

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It's a wild ride. It really is. OK, let's unpack

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this because we have to start with the sheer

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geographical audacity of this entire operation.

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We really do. We're talking about the 1980s and

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the 90s here. Sly Green, born in Buffalo, founds

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this crew and they call themselves the LA Boys.

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Right. And they didn't get that name because

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they were wearing Lakers jerseys or something.

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No, definitely not. The name came directly from

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their logistics. They were sourcing their supply

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of narcotics all the way from Los Angeles. All

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the way across the country. Exactly. Think about

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the physical distance there. You are moving illegal

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product from the Pacific coast all the way across

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the entire country to upstate New York. Right.

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What's fascinating here is the staggering level

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of organizational capability that actually requires.

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Yeah, I mean, setting up an LA to Buffalo pipeline

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in that era is like trying to run an Amazon distribution

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network. Yeah, exactly. But, you know, your delivery

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trucks are constantly at risk of being hijacked,

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the product carries a mandatory minimum prison

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sentence, and you're coordinating your whole

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logistics department on public pay phones. And

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you're doing it with untraceable cash that physically

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weighs more than the product itself. Oh, wow.

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I didn't even think about the weight of the cash.

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Yeah, it's massive. And popular culture often

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conditions us to think of a gang as this hyperlocal

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neighborhood crew fighting over just a few blocks.

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Right, like turf wars. Exactly. But organizations

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operating on the transcontinental scale of the

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LA boys, these are complex, corporate -level

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enterprises. Maintaining a supply chain across

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2 ,500 miles in the 80s meant managing couriers,

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bribing the right people across multiple state

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lines. Right, the logistics are insane. Yeah,

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and anticipating law enforcement, maintaining

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strict operational security without any encrypted

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digital communications. No signal or WhatsApp

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back then. None at all. Well, the sources show

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it paid off astronomically for them. They were

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making millions. Millions. But Sly Green... wasn't

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just coasting on being a millionaire. Court evidence

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later revealed he was actively plotting to make

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50 million dollars off these deals. It's hard

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to even fathom. 50 million? in the 80s and 90s.

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If you adjust that for inflation, you're looking

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at well over $120 million today. That is a mid

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-sized, legitimate corporation. It really is.

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And conceptualizing an illicit enterprise of

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that magnitude requires a deeply visionary, albeit

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destructive mind. To scale to a $50 million target,

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you're no longer just selling on the street.

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You are managing macroeconomic forces. Wow, macroeconom

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- Yeah, you have to understand shifting market

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demand, manage massive operational overhead,

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and ruthlessly eliminate any local competition

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that threatens those profit margins. And he built

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this corporate structure using these deeply entrenched

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familial and neighborhood networks. Right. Trust

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is everything. Exactly. Sly's brother Clayton

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Green who went by the legendary moniker iceberg

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iceberg, right? Yeah He was a core member of

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the LA boys and what really stands out in the

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sources is the resilience of these networks How

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do you mean well the LA boys golden era was the

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80s and 90s, right? But the records note that

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iceberg was actually arrested in a police raid

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in 2006 where cocaine was found. Oh, wow. 2006.

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Yeah, that is decades after the initial rise

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of the gang. If a legitimate tech startup loses

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its CEO, the whole thing solds in a month. But

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here, the infrastructure survives. It perfectly

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illustrates how deeply rooted illicit economies

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become within a community. When the leadership

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of a legitimate business is removed, the corporation

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dissolves. But in the underworld, the demand

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remains completely constant. People still want

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the product. Exactly. The trade routes, the clandestine

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connections, the methods of evasion, they're

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passed down or absorbed by the next generation.

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The infrastructure simply adapts. But, you know,

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an organization moving $50 million of product

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across state lines faces a massive vulnerability.

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Yeah. Enforcement. Right. You don't have corporate

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lawyers to enforce your contracts. You don't

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have an HR department for disputes. No, you definitely

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don't. So when a rival tries to undercut your

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supply chain, how do you protect your market

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share without a legal system? You resort to the

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streets. Exactly. Which brings us to the day

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-to -day reality in Buffalo. The LA boys were

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notorious for their extreme violence. Very notorious.

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They became one of the most powerful gangs in

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the area. And there is this one specific incident

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in the sources that reads like an absolute hallucination.

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Oh, the car chase. Yes. Sly Green is involved

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in this high -speed vehicle pursuit. He's chasing

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down a rival dealer known as Fat Richard. Right,

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Fat Richard. And during this chase, at high speeds,

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Sly Green literally attempts to jump out of his

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car and into Fat Richard's moving vehicle. It's

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just, it's unbelievable. He is trying to board

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a rival's car, like a pirate boarding a galleon

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on the interstate. Yeah. I mean, I have to push

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back on the mastermind label here for a second.

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OK, go ahead. If you are the CEO of a $50 million

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enterprise, Why are you doing pirate boardings

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on the highway? It sounds counterintuitive. It

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seems incredibly reckless. Doesn't this completely

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contradict the image of a strategic corporate

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operator? I mean, it looks completely absurd

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to a civilian, sure. It looks like an action

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movie stunt rather than a boardroom strategy.

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But in the illicit economy, the rules of leadership

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and market dominance are entirely inverted. Inverted

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how? Extreme violence and audacious displays

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of fearlessness. They act as both your marketing

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department and your primary deterrent. Wait,

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marketing? Yeah. Are you saying the violence

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isn't just a loss of temper, but like an actual

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calculated deterrent? Exactly. Like hanging a

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trespassers will be shot sign on a 50 million

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dollar bank vault. That is exactly the mechanism

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at play. Sly Green cannot sue Fat Richard in

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civil court for encroaching on his territory,

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right? Right, obviously not. So in a world completely

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devoid of legal protection, your reputation for

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being unhinged, for being willing to cross lines

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that other people are simply too terrified to

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approach that, is your ultimate armor. Oh, wow.

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I see. The game theory of the streets dictates

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that your rational behavior is actually a strategic

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asset. Because it makes you unpredictable. Exactly.

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When the story circulates through Buffalo, that

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sly green will literally launch his body into

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your moving car during a high -speed chase just

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to get his hands on you. The calculus for his

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rivals changes. Yeah, nobody wants to deal with

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that. Right. Who's going to want to steal from

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a man who seemingly has no instinct for self

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-preservation? So the sheer recklessness is actually

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this deeply calculated asset. It is. You're broadcasting

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a message to the entire city. Do not mess with

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my supply lines, because I am not bound by the

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normal laws of human survival. It's terrifying,

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but the internal logic is actually completely

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sound. It secures absolute loyalty from subordinates

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and forced compliance from rivals. Right. The

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danger, however, is that the mindset required

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to launch yourself between moving cars doesn't

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simply switch off when the environment changes.

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Ah, yeah. The environment definitely changed.

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The very audacity that builds the empire is almost

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universally the exact trait that brings it crashing

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down. And that transition from the streets to

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the cell is jarring because that audacity didn't

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just follow him. It handed the authorities the

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exact tools they needed to destroy him. It really

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did. Here's where it gets really interesting.

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In 1991, green. is arrested on murder charges.

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Okay. He is sitting in a holding facility. Put

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yourself in that environment for a second. You

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are facing life behind bars. Right, the stakes

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couldn't be higher. The smart play is absolute

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silence. Speak to no one. But what does Sly Green

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do? He talks. He shows another inmate a collection

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of newspaper clippings about the LA boys. It's

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just wild. He is literally pointing at the articles,

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bragging, saying, these are my guys. This is

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what they're doing. Why? I mean, it's like bringing

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a heavily researched portfolio of your own felonies

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to a networking event. Ha! Yeah, that's exactly

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what it is. I'm really trying to deduce the logic

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here. He's already in custody for murder, and

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he is essentially providing a masterclass on

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his ongoing active criminal enterprise to the

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guy in the bunk next to him. This raises an important

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question about the psychology of criminal hubris.

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Yeah, explain that to me. Well, at a certain

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point in the life cycle of a gangster of this

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magnitude, the bland overtakes the biological

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instinct for survival. The brand. Yeah. Sly Green

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spent years meticulously cultivating this mythical,

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untouchable status in Buffalo. Right, jumping

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between cars and all that. Exactly. The LA boys

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weren't just a business. They were his entire

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identity. Wow, yeah. To sit in a concrete cell

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and be reduced to just an inmate number that

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was likely a psychological impossibility for

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him. He couldn't handle being a nobody. Right.

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Those newspaper clippings were his proof of existence.

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They were tangible evidence that he mattered,

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that he manipulated the world outside those walls.

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Even if that proof was literally handing federal

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prosecutors the exact narrative they needed to

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dismantle his life's work. Exactly. It's a fatal

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blind spot. His desperate need for recognition

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completely eclipsed his strategic intelligence.

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Yeah. And the justice system, which had been

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tracking the chaos of the LA boys for years,

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was perfectly positioned to capitalize on that

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ego. Oh, they didn't just capitalize. They dropped

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a nuclear bomb on the organization. They really

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did. Let's talk about the sweep that followed,

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because it was structural and just. Devastating.

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On March 30th, 1994, after a grueling seven -week

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trial presided over by Judge John Thomas Curtin,

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27 members of the gang were found guilty. 27

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at once. Yeah. And the charges were heavy. Racketeering,

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conspiracy, obstruction of justice. Very serious

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charges. For anyone not familiar with how these

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specific laws work, a seven -week trial with

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27 co -defendants isn't just a standard prosecution.

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Not at all. How does a law like racketeering

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actually function to take down a whole empire

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all at once? Well, it's a phenomenal legal tool,

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and it's specifically designed to pierce the

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corporate veil of a street gang. Normally, a

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boss like Sly Green insulates himself, right?

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He gives an order, but the foot soldiers commit

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the actual crimes. So his hands are clean, technically.

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Exactly. If you arrest the foot soldier for selling

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drugs, the boss remains untouched. But racketeering

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laws like ICO allow prosecutors to draw a massive

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legal circle around the entire group. They prove

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that the organization itself is a corrupt enterprise.

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Once they establish that the LA boys exist as

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a racketeering enterprise, the leadership can

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be held directly responsible for the murders,

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the drug trafficking, and the extortion committed

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by anyone within that circle. That's incredibly

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powerful. It is. They aren't prosecuting 27 isolated

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incidents, they're prosecuting the organism itself.

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Which explains the sheer scale of the convictions.

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They essentially cut off the head and the limbs

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simultaneously. Exactly. And we really have to

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highlight the prosecution side of this war. Attorney

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William J. Hochul Jr. was a frequent formidable

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adversary to Green and his associates. He was

00:13:07.570 --> 00:13:10.250
relentless. He really was. He was the one who

00:13:10.250 --> 00:13:13.169
argued those massive 1994 convictions. Right.

00:13:13.450 --> 00:13:16.090
And his campaign didn't end there either. He

00:13:16.090 --> 00:13:19.409
later argued the 1996 murder trial of another

00:13:19.409 --> 00:13:22.690
core L .A. boys member, George Powell, known

00:13:22.690 --> 00:13:25.789
as Dog. Dog Powell, yeah. Hochul seemed to treat

00:13:25.789 --> 00:13:28.909
the L .A. boys not just as criminals, but as

00:13:28.909 --> 00:13:31.330
a systemic virus that needed to be aggressively

00:13:31.330 --> 00:13:34.309
eradicated from Buffalo's bloodstream. It was

00:13:34.309 --> 00:13:37.289
a highly coordinated campaign of judicial eradication.

00:13:37.370 --> 00:13:39.750
Yeah. The state recognized the 50 million dollar

00:13:39.750 --> 00:13:42.149
ambition. They recognized the transcontinental

00:13:42.149 --> 00:13:44.789
logistics and they responded with overwhelming

00:13:44.789 --> 00:13:47.269
legal force. And they didn't hold back. No, they

00:13:47.269 --> 00:13:49.669
needed to make an absolute undeniable example

00:13:49.669 --> 00:13:51.929
out of Sly Green. And the numbers definitely

00:13:51.929 --> 00:13:55.269
reflect that. Green tried to fight it. He appealed,

00:13:55.269 --> 00:13:58.230
but he was found guilty again on March 27th,

00:13:58.309 --> 00:14:01.919
1997. Right. Interestingly, He had actually filed

00:14:01.919 --> 00:14:04.720
a request for his trial to be extended, but that

00:14:04.720 --> 00:14:07.159
was firmly denied in December of that year. The

00:14:07.159 --> 00:14:10.500
courts were done humoring him. Exactly. Then

00:14:10.500 --> 00:14:13.600
the hammer finally falls. The sentence handed

00:14:13.600 --> 00:14:16.419
down to Donald Slygreen was just staggering.

00:14:16.559 --> 00:14:19.700
It's unbelievable. Four consecutive life sentences

00:14:19.700 --> 00:14:24.240
plus 110 years. Yeah. Four life sentences plus

00:14:24.240 --> 00:14:27.720
a century is obviously a mathematical impossibility

00:14:27.720 --> 00:14:29.980
for a human lifespan. Unless it's a vampire or

00:14:29.980 --> 00:14:32.940
something. Exactly. But it serves a profound

00:14:32.940 --> 00:14:35.879
symbolic function. Right. The justice system

00:14:35.879 --> 00:14:38.360
is using that number to communicate a message

00:14:38.360 --> 00:14:41.879
to the public and specifically to any rival gangs

00:14:41.879 --> 00:14:45.279
watching the outcome. Send a message. Yeah. They're

00:14:45.279 --> 00:14:47.940
stating unequivocally that this individual is

00:14:47.940 --> 00:14:50.340
being conceptually erased from human society.

00:14:50.639 --> 00:14:53.139
Erased. It's the ultimate period at the end of

00:14:53.139 --> 00:14:54.940
the sentence. And logically that should be the

00:14:54.940 --> 00:14:57.299
end of the tape, right? You would think so. You

00:14:57.299 --> 00:14:59.460
lock someone in a box for multiple lifetimes,

00:14:59.600 --> 00:15:02.500
you throw away the key, and public memory naturally

00:15:02.500 --> 00:15:06.509
moves on. Neighborhoods change, streets get repaved,

00:15:06.649 --> 00:15:09.470
new names pop up, and the old kingpins just sort

00:15:09.470 --> 00:15:12.429
of fade into obscure cautionary tales. They become

00:15:12.429 --> 00:15:15.370
ghosts. Right, he should be a ghost. So what

00:15:15.370 --> 00:15:18.090
does this all mean? We are back to our initial

00:15:18.090 --> 00:15:22.129
paradox. Yes. How do we reconcile a man who is

00:15:22.129 --> 00:15:25.679
physically exiled from society? permanently entombed

00:15:25.679 --> 00:15:28.639
in the federal prison system, but who is currently

00:15:28.639 --> 00:15:31.860
touring the globe via Spotify algorithms. If

00:15:31.860 --> 00:15:34.019
we connect this to the bigger picture, it really

00:15:34.019 --> 00:15:36.820
requires a pivot from examining criminal justice

00:15:36.820 --> 00:15:39.519
to examining the mechanics of cultural preservation.

00:15:39.659 --> 00:15:41.720
Cultural preservation, okay. Yeah. The state

00:15:41.720 --> 00:15:44.659
mandated erasure, but the culture issued a reprieve.

00:15:44.740 --> 00:15:46.960
Oh, that's a great way to put it. Because decades

00:15:46.960 --> 00:15:49.159
after Judge Curtin handed down that mathematically

00:15:49.159 --> 00:15:52.049
impossible sentence, Sly Green's name is thriving.

00:15:52.190 --> 00:15:55.049
It really is. He is frequently and prominently

00:15:55.049 --> 00:15:57.590
mentioned by acclaimed Buffalo rappers like Westside

00:15:57.590 --> 00:16:00.309
Gunn and Benny the Butcher. Very prominent figures

00:16:00.309 --> 00:16:03.649
in hip hop right now. Huge figures and the context

00:16:03.649 --> 00:16:06.769
here is vital. Both of these artists have been

00:16:06.769 --> 00:16:09.610
very open about being drug dealers themselves

00:16:09.610 --> 00:16:13.700
in Buffalo during the 90s and 2000s. Right. They

00:16:13.700 --> 00:16:16.679
share the exact same geography, the exact same

00:16:16.679 --> 00:16:19.500
concrete as the LA Boys. And that's the key.

00:16:19.639 --> 00:16:22.159
They aren't researching him in a municipal archive.

00:16:22.379 --> 00:16:25.019
No, definitely not. They lived in the geopolitical

00:16:25.019 --> 00:16:28.240
environment that Sly Green's $50 million ambition

00:16:28.240 --> 00:16:31.720
violently shaped. The blast radius of the LA

00:16:31.720 --> 00:16:34.059
Boys literally formed the conditions of their

00:16:34.059 --> 00:16:36.600
youth. Exactly. And it bleeds directly into the

00:16:36.600 --> 00:16:39.740
art. Like, Benny the Butcher has a track. literally

00:16:39.740 --> 00:16:42.500
titled Sly Green on his critically acclaimed

00:16:42.500 --> 00:16:45.840
2020 album, Burdened of Proof. Great album. Yeah.

00:16:46.279 --> 00:16:48.779
And West Side Gun featured Green on the Sly Green

00:16:48.779 --> 00:16:51.519
skit all the way back on his 2016 album, Fly

00:16:51.519 --> 00:16:53.980
God. Right. But then it escalates to a surreal

00:16:53.980 --> 00:16:57.259
level in 2024. On West Side Gun's EP, titled

00:16:57.259 --> 00:16:59.779
11, Sly Green is featured on every single song.

00:16:59.919 --> 00:17:02.480
Think about the mechanics of that. You have a

00:17:02.480 --> 00:17:04.920
man calling from a federal penitentiary, likely

00:17:04.920 --> 00:17:07.420
using a heavily monitored prison phone system,

00:17:07.980 --> 00:17:11.240
and his voice is being layered over premium studio

00:17:11.240 --> 00:17:14.029
production. seamlessly integrated into modern

00:17:14.029 --> 00:17:17.410
hip hop and pushed to millions of listeners worldwide.

00:17:17.690 --> 00:17:21.190
It's wild. And it clearly shows how hip hop functions

00:17:21.190 --> 00:17:24.509
as an alternative, deeply vital oral history

00:17:24.509 --> 00:17:27.049
for cities like Buffalo. Right. The mainstream

00:17:27.049 --> 00:17:29.829
historical record, you know, the court transcripts,

00:17:29.890 --> 00:17:32.329
the newspaper clippings, Sly Green kept in his

00:17:32.329 --> 00:17:34.869
cell that tells the state's version of the city's

00:17:34.869 --> 00:17:36.910
story. Right, the official record. But hip hop

00:17:36.910 --> 00:17:39.309
acts as the unredacted archive for the streets.

00:17:39.529 --> 00:17:41.910
I love that. Artists like West Side Gun and Benny

00:17:41.910 --> 00:17:44.910
the Butcher, they invoke figures like Sly Green,

00:17:45.269 --> 00:17:48.230
not as moral role models to emulate, but as foundational

00:17:48.230 --> 00:17:50.809
cultural touchstones. They use them the way a

00:17:50.809 --> 00:17:53.009
historian might use a landmark. Right. To prove

00:17:53.009 --> 00:17:55.650
they were actually there. Precisely. To understand

00:17:55.650 --> 00:17:58.509
the grit, the paranoia, and the survival instincts

00:17:58.509 --> 00:18:00.769
embedded in their music, the listener has to

00:18:00.769 --> 00:18:03.410
understand the titans that roamed those specific

00:18:03.410 --> 00:18:05.509
Buffalo neighborhoods when these artists were

00:18:05.509 --> 00:18:07.809
coming of age. That makes a lot of sense. By

00:18:07.809 --> 00:18:12.180
putting Sly Green's act - voice on an EP in 2024,

00:18:13.099 --> 00:18:16.079
they're authenticating their own lived experiences.

00:18:16.339 --> 00:18:19.859
They're essentially telling the audience, I survived

00:18:19.859 --> 00:18:23.200
the era of the LA boys. I am a product of the

00:18:23.200 --> 00:18:25.799
pressure cooker that he built. It really reframes

00:18:25.799 --> 00:18:27.599
the entire narrative we just walked through.

00:18:27.599 --> 00:18:30.319
It does. The state utilized millions of taxpayer

00:18:30.319 --> 00:18:33.519
dollars, a seven week trial, racketeering laws,

00:18:33.579 --> 00:18:36.160
and a sentence of four lifetimes to erase him.

00:18:36.680 --> 00:18:40.819
But the culture utilized a microphone and an

00:18:40.819 --> 00:18:44.059
algorithm to immortalize him. It's wild to step

00:18:44.059 --> 00:18:46.759
back and look at the trajectory here. We started

00:18:46.759 --> 00:18:48.900
with a local Buffalo kid who looked at a map,

00:18:49.359 --> 00:18:52.099
pointed 2 ,500 miles away to Los Angeles, and

00:18:52.099 --> 00:18:54.720
built a massive logistical drug pipeline fueled

00:18:54.720 --> 00:18:57.940
by a $50 million dream. And we saw him enforce

00:18:57.940 --> 00:19:00.319
that dream by completely inverting the rules

00:19:00.319 --> 00:19:03.019
of self -preservation, jumping into the moving

00:19:03.019 --> 00:19:05.900
vehicle of arrival just to market his own terrifying

00:19:05.900 --> 00:19:08.859
unpredictability. Then we watched that same unyielding

00:19:08.859 --> 00:19:11.759
hubris flashing newspaper clippings in a holding

00:19:11.759 --> 00:19:13.980
cell to maintain his brand and did the federal

00:19:13.980 --> 00:19:16.480
government the exact blueprint they needed to

00:19:16.480 --> 00:19:19.359
legally bury him under a mountain of centuries.

00:19:19.920 --> 00:19:21.980
Only for him to orchestrate his own resurrection

00:19:21.980 --> 00:19:25.460
decades later, bypassing the prison walls entirely

00:19:25.460 --> 00:19:28.779
to become a recurring vocal presence in the machinery

00:19:28.779 --> 00:19:31.079
of modern music. It's unbelievable. I want you

00:19:31.079 --> 00:19:33.720
to consider how the media, the music and the

00:19:33.720 --> 00:19:36.779
art you passively consume on your daily commute

00:19:36.779 --> 00:19:41.410
are so often built on the very real very dark

00:19:41.410 --> 00:19:43.690
histories of local neighborhoods. Absolutely.

00:19:43.809 --> 00:19:45.930
The entertainment we stream is frequently echoing

00:19:45.930 --> 00:19:48.609
the most dangerous eras of cities we might never

00:19:48.609 --> 00:19:51.529
even visit. Right. The ghosts of these underworld

00:19:51.529 --> 00:19:54.490
empires are quite literally speaking to us through

00:19:54.490 --> 00:19:57.349
our headphones. It's a profound reminder that

00:19:57.349 --> 00:19:59.930
history isn't just locked away in court vaults

00:19:59.930 --> 00:20:02.809
or textbooks. No, it's not. It's actively encoded

00:20:02.809 --> 00:20:04.750
and transmitted through the art that survives

00:20:04.750 --> 00:20:07.309
the era. And it leaves you with a really strange

00:20:07.309 --> 00:20:10.069
philosophical question for the digital age. What's

00:20:10.069 --> 00:20:12.289
that? If an inmate serving four consecutive life

00:20:12.289 --> 00:20:15.009
sentences can literally be a featured artist

00:20:15.009 --> 00:20:18.940
on an entire music EP Where exactly is the line

00:20:18.940 --> 00:20:21.279
between incarceration and influence? That's a

00:20:21.279 --> 00:20:23.559
great question. As technology and algorithms

00:20:23.559 --> 00:20:26.079
make it easier to broadcast a voice from absolutely

00:20:26.079 --> 00:20:29.180
anywhere, even a federal supermax, will the justice

00:20:29.180 --> 00:20:32.680
system's ability to erase a kingpin from society

00:20:32.680 --> 00:20:35.900
become completely obsolete? It might. Could you

00:20:35.900 --> 00:20:38.619
truly lock a man away if his voice is on a million

00:20:38.619 --> 00:20:40.720
smartphones? It's fascinating to think about.
