Yo what's good evil streets fam, y'all know the deal we back at it again with another one, major shoutout to all my members and subscribers for locking in on the daily, y'all really the backbone of this channel's grind and come-up. Anybody tryna push their music, brand, or hustle, hit me at evil streets media at gmail.com, we can make some moves happen. Real talk I'm grateful for all the cash app love too, and anybody trying to throw support to the channel can slide it through at evil streets tv on cash app, every dollar goes right back into building this thing up. Aight y'all let's dive into this gangster shit.
Sometimes you step into wars where the outcome already written, no matter how hard you go. Theodore Teddy Roe knew that reality all too well, being a Black man coming up in America during the early 1900s, the deck was stacked heavy against him from jump, but he ain't give a damn, he pushed all his chips to the center, and by the 1950s he became one of the biggest crime bosses Chicago ever seen, and also a man the mafia had marked for death. But Roe stood firm and stared right back at them.
To say it was guaranteed that Roe would reach such a major position in the game would be straight lies. Born August 26th, 1898 in Galeano, Louisiana to a tenant farmer, Roe's future wasn't looking too promising. America claimed to be the land of opportunity, but not for a light-skinned African-American born down south. Roe grew up in Little Rock, Arkansas. By the time he hit his twenties he was bouncing between gigs, even worked as a bootlegger during prohibition. Back then you could call that an honest hustle seeing how everybody hated prohibition across all walks of life. Still, the work came with major risks. The profits were crazy and gangsters stayed ready to squeeze the trigger to protect their cut of the pie.
When Roe married his true love Carrey in 1923, he decided to calm down and search for something more secure. The couple relocated to Detroit where Roe started grinding in the exploding car industry. Unfortunately, it fell apart, he lost his position. Unemployed and lost about what moves to make next, Roe did what mad African Americans, especially those coming from the broke and racially divided southern states did back then. He relocated to Chicago.
As tens of thousands of African Americans poured into the city of Chicago throughout the 1910s and 1920s, they discovered that opportunities weren't much better there than they were down south. Jobs were scarce and housing was garbage to keep it real. Racism ran wild and Blacks were separated from white residents as they settled on Chicago's south side. Due to the heavy concentration of African Americans and Black-owned businesses, homes and churches, it became known as the Black belt.
With so many African Americans searching for work and so few jobs available, it was survival of the fittest. Many African Americans decided to just do it themselves, white banks wouldn't accept their money, they launched their own banks. They get no or terrible insurance, Black insurance companies popped up immediately, and so on it went. Still not everybody managed to build such a successful life for themselves in what still was a poverty-stricken ghetto. One had to be creative, others had to gamble. Mix the two together and you got the policy game.
Policy is a lottery where you bought a ticket and picked a number. At a drawing, numbers were called out and if you had one of those numbers, you won. At a drawing, seventy-eight numbers, numbers one to seventy-eight were wrapped in a container and dropped in a drum shaped receptacle known as a wheel. Players picked a combination of numbers, usually three.
The policy game was a massive hit in the Black belt as it gave everyone from poor to rich the chance to play and make some real nice cash. The gamblers loved the odds and the winning amounts. But it was those that operated the policy games or wheels that made the serious bread. That's facts, that money circulated through the neighborhood, gamblers bet and won or lost, while operators won and expanded their business. They employed thousands of workers to handle bets, move money, keep account of everything, etc. Winning bettors spent their money in the Black belt, while the policy operators offered various new jobs as part of their lottery or the investments they made in the local business scene.
In the 1930s, the Jones Brothers, Edward, George, and McKissick who was simply called Mac, ran one of the most profitable policy games in the city. Led by Edward, the brothers were sharp and educated. They approached the policy game like the major business that it was, studying it from every angle and checking out how other operators ran their wheels. They ran their first game out of the family's tailor shop on 42nd Street. To make sure they had enough players, they promoted the event using handbills at barbershops and dances. It worked, and within a month they had one of the most successful games in the area, pushing competitors out of business.
When Roe arrived in Chicago, he ended up working for Ed Jones as a bookkeeper and began experimenting with running a policy game. Asked how one could place a bet, Roe answered, well some writers go from door to door and the people play on their book, and they have some place they turn their book in, and then there are stations where they go to play. Most stations started out very low key and simple, but the ones run by the Jones Brothers had turned into something straight out of Las Vegas before that city was even built. Ed Jones hired beautiful women to host the stations and offered other forms of gambling like crap games and blackjack at the same venue.
As the decade neared its end, the Jones Brothers were among the richest African Americans in the United States. Their gambling empire consisted of casinos and policy wheels and earned them an estimated two million dollars a year, which would be forty-five million in 2025. Roe was right there with them, watching and earning.
He also saw how all that wealth attracted the attention of the IRS. The federal agency discovered that Ed Jones had personally spent over $1.6 million during a six-year period. It also found that between 1933 and 1938, the brothers had spent $2.7 million but only paid taxes on $1.3 million. Faced with the evidence against him and in return for dropping the case against his brothers, Ed Jones decided to plead guilty. He was sentenced to two years behind bars, the government got him like they got Al Capone, death and taxes baby.
In prison, Jones became close to Sam Giancana, a lowly member of the Chicago Outfit, the city's Cosa Nostra family once ruled by Capone. Giancana had a reputation for violence and being a little crazy, but Jones took a liking to him. Whether it was the boredom of being locked up or the genuine connection, Jones told Giancana all about the policy game, the money made, the men needed, all the intricacies of the racket. Jones trusted the mafia soldier, he shouldn't have.
Once released from prison, Giancana set about organizing a hostile takeover of the policy games in the Black belt. He saw it as his ticket to becoming a big power in the mob, rightly so. His bosses appreciated his keen eye for more riches and the way to go about it, and gave him their blessing and the full backing of the organization. Of course, he didn't tell Jones this. Giancana kept his prey close and put on a friendly smile as he lulled him asleep and swayed him with profitable investments and partnerships.
Roe watched the friendship between Jones and Giancana with suspicion. He warned his friend to steer clear of the mobster. By now, the mid-1940s, Roe had climbed up the ranks and become a policy king in his own right. He had a fondness for the finer things in life. He wore custom made suits, monograms, silk shirts, alligator shoes, painted ties, and wide brimmed hats. He even spent $50,000 to decorate his flat. It had a living room with a fireplace made completely of mirrors and a six-foot high television set, which was placed on a turntable so you could turn it any way you wanted when watching TV by pressing just one button. Pretty high tech for those days.
But don't let the flashy lifestyle fool you. Teddy Roe was a hard man and had no problem being violent. He had a hair trigger temper and was nice with his fists. If someone came at him, he came back at them tenfold. It was the only way to survive the volatile streets of Chicago in the 1930s and onward. Roe took no shit from anybody and he wasn't about to start bowing down to a guy like Giancana. Not that Giancana was asking him to. The mafia wasn't done with their slow play yet.
By the late 1940s, Giancana's grip on the policy racket was tightening. He muscled out the Jones Brothers and took control of their operations. He had the Outfit backing him, the most powerful criminal organization in the Midwest, so resistance seemed futile. But Teddy Roe wasn't most people. While other Black policy operators either folded or paid protection money to Giancana and the mob, Roe refused to bend the knee. He kept his operations running independently, kept his money flowing, and most importantly, he kept his pride intact.
This defiance made Roe a target. The Outfit didn't appreciate any Black man refusing their authority or their cut of the profits. They sent messages through violence and intimidation, but Roe stayed resolute. He had security around him at all times, moved unpredictably, and made sure his people were loyal. For years, a dangerous equilibrium existed between Roe and the Chicago Outfit. They wanted him dead, but he was too smart, too careful, and too well protected to give them an easy opportunity.
Roe's reputation grew in the Black belt. He wasn't just a gangster making money off gambling, he was a symbol of Black independence and resistance against the mafia's control. He employed thousands of people, invested in Black businesses, and became something of a folk hero to many in the community. When Roe walked down the street wearing one of his custom suits and alligator shoes, people knew they were looking at a man who had refused to bow.
But legends can't last forever in the streets. On November 1st, 1952, Teddy Roe was shot and killed in his Cadillac on South Cottage Grove Avenue. The hit was carried out by the Chicago Outfit, finally eliminating the one Black policy king who had dared to stand against them. His death sent shockwaves through the Black belt, signaling to every other operator that resistance would not be tolerated.
Theodore Roe's legacy, however, transcended the manner of his death. He represented something powerful and meaningful in the struggle of African Americans during the mid-twentieth century. In a time when Black people were systematically excluded from legitimate economic opportunities, Roe built an empire through sheer will, intelligence, and refusal to accept the subordinate position society had assigned to him. He didn't just survive in a rigged game, he thrived and accumulated wealth that rivaled that of the most powerful white businessmen of his era. And when faced with organized crime's attempt to steal what he had built, he chose dignity over capitulation. Teddy Roe died on his own terms, never submitting to the mob, never surrendering his independence, and never forgetting who and what he was. In the streets of Chicago, and in the hearts of those who knew his story, Theodore Roe remains immortal—a testament to the power of Black resilience, pride, and the audacity to dream big in a world designed to keep you small.