All right, y’all. Real quick before we get into today’s story. In the last video, I asked y’all to drop some names, people you wanted me to cover next. Man, I’m not even going to lie, I wasn’t expecting that many suggestions. Y’all really showed up in the comments. I appreciate that more than you know, for real.
I’m going to do my best to get through as many of those requests as I can, so keep dropping them. I see them, and seriously, thank y’all for rocking with the channel like this. The support means a lot to me, but today, we’re getting into the story of Angelo Roberts. So, let’s get into it. January 1995, Chicago’s West Side, a brown Chevy sits on a frozen street.
Nobody calls it in right away. This is the West Side, people learn not to look. When they finally open the trunk, the body is frozen stiff. A wound to the throat, hands bound. He was 24 years old, and 7 months as a free man, this man had allegedly ordered the assassination of his own gang’s founder. He had planned a military weapons deal from inside a prison cell.
He had declared all-out war on the Chicago Police Department. The FBI wanted him, the ATF wanted him. America’s Most Wanted put his face on television. Nobody caught him, someone else got there first. His name was Angelo Roberts. The streets called him Low. No one was ever charged with his murder. The case is cold to this day.
This is his story. This story don’t actually start with Angelo Roberts. No, it starts with a building, Henry Horner Homes, West Side of Chicago. Eight blocks of concrete towers they threw up back in 1957, built on the cheapest budget the city could get away with. Cinder block walls, steel elevators sitting wide open to the elements.
No doors, no lobby, no buzzer system, just a tunnel running straight through the building. Anybody could come through there. In and out just like the wind. They built it as a solution to urban poverty. What they actually built was a cage. Now, let me paint the picture for you real quick. You’re 9 years old living on the seventh floor.
Elevator been broken for 3 weeks. So, every day you climbing them same stairs and the stairwell smell like piss. Blood still dried up on the landing from a shooting that happened the week before. And the crazy part, that ain’t some terrible week. That’s just Tuesday. That is Henry Horner Homes. By the early 1990s, the federal government made it official.
Henry Horner was declared the most distressed public housing property in the entire United States. Not one of the worst, the worst full stop. And the gangs didn’t just operate inside those buildings, they owned them. Floor by floor, building by building. The Gangster Disciples controlled certain towers, the Traveling Vice Lords held others, the Gangster Stones claimed their turf around 150 Lake Street, and the Four Corner Hustlers, the gang at the center of this story, they were embedded in there, too, fighting for every block. Drug wars weren’t fought in the streets, they were fought in stairwells, in elevators, in hallways where children slept on the floor to avoid stray bullets coming through the windows. The journalist Alex Kotlowitz spent years living inside Henry Horner documenting two brothers trying to survive it. His book, published 1991, became one of
the most important pieces of American journalism of the 20th century. The title came from a mother who lived there. She said of her own children, “There are no children here. They’ve seen too much to be children.” That line stuck with me. Cuz somewhere in those same towers, in that same world, during those same years, there’s a young dude named Angelo Roberts out there moving through those streets.
He ran with the gang the Stones. That much we know. No journalist followed him. No book documented his childhood. The record of who Angelo Roberts was before the streets claimed him is almost completely silent. What we have is the world, and the world tells you everything. Because in 1987, a man named Monroe Banks walked out of prison with a plan that would change everything on Chicago’s West Side.
And Angelo Roberts, young, hungry, and living in the most dangerous housing project in America, was exactly the kind of person Monroe Banks was looking for. Before Angelo Roberts, there was Walter Wheat. And before Walter Wheat, there was a playground, West Garfield Park, 1968. Two young men, Walter Wheat and Freddy Gage, break away from the Unknown Vice Lords and start something of their own.
They call it the Four Corner Hustlers. Colors, black and brown. Territory, four corners. Six square blocks on Chicago’s West Side. Six blocks. That’s it. That’s where this whole story begins. And the Chicago Tribune would write something later on, and this line always stuck with me. There was a time when the Four Corner Hustlers really meant four corners.
Just a small set about six square blocks out on the West Side. Six blocks. That’s it. That article came out in 1994 and by that point, those same six blocks had turned into something so big, it took federal indictments just to try to contain it. But in the beginning, Walter Wheat ran a tight ship. Original code protect the neighborhood.
No praying on your own people. No drugs. Wheat was firm on that. The Four Corner Hustlers in their earliest form were, by the standards of Chicago’s West Side, almost disciplined. Through the 1970s, they allied with the Vice Lords and folded into the People Nation, one of Chicago’s two great gang alliances.
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They adopted the symbols that would define them. The top hat, the cane, the glove. Small gang, loyal. Wheat’s word was law. Then the 1980s arrived and the crack epidemic hit Chicago like a freight train. Monroe Banks, known on the streets as Money, got out of prison in 1987 with a vision so ambitious, it immediately put him at odds with the man who built the organization.
Banks wanted to pivot the entire gang to crack cocaine distribution. He wanted to sever ties with the Vice Lords completely. He wanted independence. Wheat said no. Banks didn’t care. He had the momentum, he had the muscle, and he had a symbol, the black diamond. Sleek, hard, unbreakable. A declaration that the Four Corner Hustlers were no longer a Vice Lord faction. They were their own nation now.
Wheat was overruled in his own organization. The man who started it all, pushed aside by the new money and the new era. This right here, this is the moment the Four Corner Hustlers stopped being just a neighborhood gang and started turning into a real criminal operation. And if you’re looking for the turning point, the one decision that set everything else in motion, this is it.
Now, here comes Angelo Roberts. He walks away from the Gangster Stones at Henry Horner. He meets Walter Wheat’s daughter. He marries her. Overnight, he is Wheat’s son-in-law, family by blood and by bond. Wheat, perhaps seeing in this young man the loyalty and the fire he valued, begins grooming him for leadership.
And Roberts gets to work immediately. He helps Banks flood the Henry Horner projects with crack cocaine, personally flipping Gangster Stones, his former crew, into Four Corner Hustlers, recruiting from the inside, expanding the territory, building the empire. Walter Wheat was investing in his son-in-law, preparing him to one day run the nation.
He had no idea what he was building toward. In 1992, with Wheat’s blessing, Roberts officially took over the Four Corner Hustlers. He was 22 years old, the youngest chief the organization had ever seen. By 1991, the Four Corner Hustlers were eating themselves alive. Monroe Banks, the man who built the crack empire, the man who pushed Walt Wheat aside and planted the Black Diamond flag, was dead.
Shot in the street sometime in the early ’90s. According to accounts later documented on the History Channel’s Gangland, Banks was killed by a Black Souls member while standing outside watching someone try to get a cat down from a tree. A cat in a tree? Honestly, I don’t even know whether that detail is tragic or just straight-up absurd.
Probably a little bit of both. But that’s Chicago gang history for you. Little moments, almost random, almost cinematic. And somehow they end up changing everything. Walter Wheat stepped back in to steady the ship. Now, remember, Roberts had already been given the keys in ’92, but keys can be taken back. With Roberts behind bars, Wheat was reasserting himself.
The old king was not finished. But here’s the problem. The streets had moved. The organization Banks built, the crack money, the black diamond independents, the new school hunger, that wasn’t going back in the bottle. A new generation of Four Corner Hustlers had tasted what the game could produce. They weren’t interested in Wheat’s original code anymore.
And then there was Angelo Roberts. Spring of 1994. Roberts catches a state conviction and gets shipped to Illinois River Correctional Center in central Illinois. Most people, when they catch a prison sentence, especially the third time, they slow down, lay low, just do their time and wait it out. But Roberts, man was built different.
By then, he’d already done time for hiding a homicide, then again for unlawful use of a weapon. Twice the system tried to shut him down, and twice it didn’t stick. So, what did Roberts do? The exact opposite. From inside his prison cell, using a phone monitored by Illinois correctional authorities, which, and I cannot stress this enough, means every single word was being recorded, Roberts reached out to a man named Darren Stacy Hardaway, his old gun supplier, a man he trusted.
What Roberts did not know was that Hardaway had already been arrested by the Bureau of Alcohol, Tobacco, and Firearms and flipped. Hardaway was now working for the ATF and every call Roberts made was being handed directly to federal agents. Roberts, completely unaware, placed his order. He wanted fully automatic M-16 rifles, two machine guns fitted with silencers, and one law anti-tank rocket, the same weapon used in Vietnam, designed to pierce armored vehicles.
ATF special agent in charge, Richard Rawlings, described it plainly to reporters. It would easily go through doors or brick walls. The target Roberts had in mind for that rocket, District 11 police station, 3151 West Harrison Street, the building he blamed, personally, obsessively, for dismantling his drug operations on the West Side.
He wasn’t talking about a warning shot. He was talking about demolition. He got out of prison in June 1994. Within a week, according to Chicago police, Tony Davis, the man running drug sales at Henry Horner in Roberts’ absence, was shot dead. A power struggle, police said. Roberts was back and he was collecting what was his.
He picked up exactly where he left off. July 14th, 1994. The exchange happens. Roberts’ crew shows up and hands over cocaine and $4,000 to men they believe are black market arms dealers. They are ATF undercover agents. The weapons are never delivered. Somewhere in the transaction, something feels wrong to Roberts. He vanishes before the arrest can be made.
Four of his associates are not so lucky. Then, 11 days later, July 25th, 1994, Walter Wheat, 43 years old, founder of the Four Corner Hustlers, sitting in his 1982 Oldsmobile Regency, parked outside a clothing store at 3815 West Chicago Avenue, waiting for friends. A 17-year-old named Bobby Cooley rides up on a bicycle, shirtless. He pulls a 9-mm pistol and fires twice.
Wheat never sees it coming. Walter Wheat, the man who built the Four Corner Hustlers from six square blocks on a West Garfield Park playground, killed by a teenager on a bicycle, killed by his own organization. Chicago Police Commander Donald Hillbring did not mince words when speaking to the press.
He said, “Roberts is trying to gain control of the Four Corner Hustlers. Apparently, Walter Wheat was standing in his way, so he had him eliminated.” It didn’t stop there. August 18th, 1994, Richard Goodwin, 40 years old, high-ranking Four Corner Hustler, old guard, shot dead on the street by Cooley. By October 20th, the federal indictments are unsealed.
Roberts and four co-conspirators charged, four arrested. Roberts gone. The FBI, the ATF, and the Chicago Police Department are now all hunting the same 24-year-old from the West Side. America’s Most Wanted puts his face on television. Commander Hillbring tells reporters, “The key guy is Angelo Roberts. He’s still out there.
He’ll still have people who will do what he tells them to do.” He was right about that. Let’s take stock of where we are. October 1994. Angelo Roberts is 24 years old. He’s wanted by the Chicago Police Department. He’s wanted by the Bureau of Alcohol, Tobacco, and Firearms. He’s wanted by the Federal Bureau of Investigation.
His face is on America’s Most Wanted. A federal grand jury has indicted him on weapons charges that carry decades in prison. And Walter Wheat, the founder of the Four Corner Hustlers, the man who was his father-in-law, the man who groomed him for leadership, is 3 months in the ground.
Most people in this situation disappear, leave the city, leave the state, start over somewhere quiet under a different name. Roberts does not disappear quietly. His crew on the West Side holds. Business continues. The drug spots keep running. The money keeps moving. Commander Hillbring, watching from the outside, tells reporters exactly what he thinks that means.
He said, “He’ll get another shooter.” Now, look. Hillbring wasn’t wrong about that. He was describing a man who, even as a federal fugitive, still had people ready to move the moment he said the word. That is a very specific kind of power, and a very dangerous kind, too. But, here is the thing about that kind of power on the streets.
It also makes you a target. Because the same people who fear you, some of them are also calculating, watching, waiting for the moment your exposure makes you vulnerable. Roberts is moving. He’s hiding. He’s surviving. Weeks pass, then months. Winter comes to Chicago the way it always does, hard and without apology.
January 1995, a brown Chevy sits on a West Side street. When someone finally checks the trunk, the body inside is frozen stiff. A wound to the throat, hands bound. The Chicago Tribune reports it on January 17th, 1995. Reporter Andrew Martin, a few paragraphs, then silence. No arrest, no suspect named publicly.
The investigation goes nowhere fast. Street accounts, and I want to be clear, these are street accounts, not court records, say Roberts did not go easily. That his killers had time with him before the end. And that through all of it, staring death straight in the face, Angelo Roberts died with the smile.
Refused to beg, refused to break, refused to give whoever killed him the satisfaction of seeing him suffer. That story’s been floating around Chicago’s West Side for almost 30 years. When something sticks that long, then it tells you something about how people chose to remember him. Now, who killed Angelo Roberts? The case is cold.
No one was ever charged. But two theories have circulated on those streets ever since. Theory one, it was internal. Older Four Corner hustlers, men who had been loyal to Walt Wheat since the beginning, men who watched their king get shot off a bicycle by a teenager Roberts allegedly sent, finally settled the debt. Blood for blood. Old school justice.
Theory two, the police. Roberts had declared all-out war on District 11. He had tried to purchase a military rocket to demolish their headquarters. Some on the West Side have always believed the Chicago Police Department, or someone connected to them, decided not to wait for the courts. Both theories remain exactly that.
Theories. What the federal courts confirmed in United States versus Haney, decided by the 7th Circuit in 1999, is this single precise line. Roberts was murdered before he could be arrested. The government had the case built, the calls were recorded, the evidence was assembled, and someone got to Angelo Roberts before the federal government could put him in front of a judge.
Bobby Cooley, the 17-year-old on the bicycle, the trigger man Roberts allegedly used to clear the board, was convicted of two murders in March of 1997 and sentenced to life in prison without parole. He was 20 years old at sentencing. Assistant State’s Attorney Kathy Cavanaugh said of him, “This guy is just a cold-blooded killer.
He was the kind of guy who celebrated death, not life.” Bobby Cooley got life. Angelo Roberts was never charged with a single murder. The man who built the empire, went to war with the police, stayed one step ahead of federal agents, and according to the streets, even had his own gang’s founder taken out.
That man ended up dead in the trunk of a car. Cold night in January. 24 years old. Case went cold. Killer still unknown. Angelo Roberts was dead. The Four Corner Hustlers were not. This is the part of the story that I think gets overlooked because Roberts burned so bright in the telling that it’s easy to assume the organization died with him. It didn’t.
If anything, what came next proved that the Four Corner Hustlers were bigger than any one man, even Lowe. Ray Longstreet stepped in, and here is where this story takes a turn that I genuinely did not see coming when I first started digging into it. Because Ray Longstreet was not just any street level successor.
Ray Longstreet was the younger brother, so much younger he was practically a generation removed of Ernest Laverne Larod Longstreet. Let me tell you who Laverne Longstreet was. 1963 Englewood, Southside of Chicago. Laverne Longstreet clears out the basement of his family home at 66th and Eggleston and convenes a meeting of the top disciples.
In that basement on that day, he creates the Disciple Nation, a federation that united the Disciple gangs of the Southside under one banner. David Barksdale would take over that federation by 1965. What he built from it would eventually split and become the Gangster Disciples and the Black Disciples, two of the most powerful and feared street gangs in American history.
Laverne Longstreet also created the pitchfork symbol. That upward pitchfork you still see in gang graffiti across Chicago today. That came from a man sitting in a basement on the Southside over 60 years ago. The man who built Chicago’s most powerful Southside gang dynasty had a little brother and that little brother took over Chicago’s most feared Westside gang.
Leadership it seems was simply in the blood. Under Ray Longstreet, the Four Corner Hustlers stopped operating like a street gang and started operating like a corporation. A 36 block empire anchored around Hamlin and Iowa on the Westside. Round the clock shifts, workers at every corner and street rent.
Long Street collected payment from every single dealer operating in his territory the way a landlord collects from tenants. You wanted to sell in his 36 blocks, you paid Ray Long Street first. The numbers the federal government documented were staggering. $50,000 per day. Federal investigators wiretapped between 3,000 and 5,000 of Longstreet’s phone calls over the course of their investigation.
3,000 to 5,000 calls. And in one of them, intercepted while Longstreet was complaining to a rival gang leader, he said simply, “The Chicago police won’t let me eat.” The man was running a $50,000 a day drug empire from a brick bungalow in Forest Park while wearing an ankle monitor. And his complaint was that the police were being unreasonable, which brings us to the ankle monitor.
Longstreet had been paroled from Stateville Correctional Center in May of 2004. He was placed under home confinement, electronic monitoring, the whole apparatus. What the federal government later documented was that Longstreet had found an opening in his parole agreement. He was permitted to leave his home between 5 and 10 p.m.
on Saturday evenings for what his agreement called recreation. Recreation every Saturday evening. That investigators discovered was when Ray Longstreet conducted business. May 25th, 2005. Operation Street Sweeper. Hundreds of federal agents and Chicago police moved simultaneously across the West Side. 34 defendants arrested, 12 search warrants executed.
Longstreet is taken from his Forest Park home that morning. The man had tattoos reading mob boss and wizard of death. He went quietly. His sentence, 456 months, 38 years in federal prison, but the Four Corner Hustlers kept going. 2017, a new federal racketeering indictment, nine members charged, six murders tied to the organization between 2000 and 2003.
Their leader, Labar Bro Man Span, convicted of racketeering conspiracy in November 2021, including four murders. That conviction was thrown out in January 2025 after it emerged a prosecutor had made an unauthorized promise to the government’s star witness. Span got a new trial. In December 2025, a second federal jury convicted him again.
He now faces a mandatory life sentence. The legal battles for Span appear to be over. The towers of Henry Horner Homes started coming down in August 1995, the same year Roberts was found frozen in that Chevy. The buildings that made him gone. His name still here. Think about what this story actually is.
A boy from the most dangerous housing project in America. No biography. No record of his childhood. Just the world that shaped him. Cinder block walls, stairwell blood stains, drug wars fought floor by floor. He married into a gang dynasty. He cleared the board. He declared war on the police.
He ran from everyone and no one caught him. Someone else did. Walter Wheat is dead. Bobby Cooley is serving life for killing him. Roberts was never charged with ordering any of it. The system that created him, the projects, the crack epidemic, the gang structure that was the only economy available to an entire generation of West Side men, kept producing the same story.
New chiefs, new operations, new federal indictments, new names. The Long Street family alone gave Chicago both the Disciple Nation and the most powerful post-Roberts era of the Four Corner Hustlers. One family, two dynasties, opposite sides of the city, decades apart. And somewhere on the West Side, on a wall, on a corner, spray-painted in the alley, it still reads, “Angelo Fours.
” Angelo Roberts ordered murders. He flooded a housing project with crack cocaine. He tried to blow up a police station. Not because he was innocent. He wasn’t. Not because he was a good man. The record suggests otherwise. But because he was 24 years old and absolutely fearless in a world that gave him nothing to lose from the moment he was born into it.
The body in the brown Chevy, the smile on his face, the case is cold, the questions remain.
