The Rise and Fall of Chicago Numbers Boss Teddy Roe Pt. 2

0 Posted by - November 26, 2020 - Black History, BLACK MEN, LATEST POSTS

It’s the 1940s and Teddy Roe is running the numbers game in Chicago’s Southside with the Jones brothers. He has been at it for over a decade now and was becoming a known figure among the poor of the city. Unfortunately, a larger force would muscle in with an intent on steamrolling all of the active numbers operations.


Roe vs. The Chicago Outfit

In 1946, Paul “The Waiter” Ricca and the Chicago Outfit started to sniff about the numbers scene on the Southside. To get their point across, the Outfit kidnapped Ed Jones and attempted to squeeze a $100,000 ransom out of Teddy Roe and Jones’ brother. The Outfit also wanted the policy business to be handed over.

Roe would pay off the ransom but refused to hand over his part of the operation. Freed, Ed Jones and his brother left Chicago entirely and Roe took over the operation. The brothers would flee to Mexico and weren’t heard from afterward.

Some years later in 1951, the Chicago Outfit made another attempt at taking the operation from Roe. At the time, the boss was Anthony “Joe Batters” Accardo. He ordered underboss Salvatore “Mooney Sam” Giancana to have Roe kidnapped.

June 19, 1951, proved to be a date that sealed Roe’s fate. During the kidnapping attempt, Teddy Roe would kill Lenny Caifano, a made man, and brother to one of the Outfit’s capos. He was arrested by the Chicago Police Department for murder and placed under heavy guard. Since he was in captivity, the police charged him with conspiracy to violate the state’s anti-gambling laws.


End of the Road for Roe

During the murder trial, Roe went the self-defense route and his team managed to show a definite connection between the Outfit and the prosecutors. With important evidence tossed out, Roe’s team was able to get him off the murder charge. In talking to the press afterward, Roe is said to have pounded his chest and declare “They’ll have to kill me to take me!”

Following the trial, Giancana targeted the Black operators, taking over businesses and trying to draw Teddy Roe out. Meanwhile, Robinhood was safe and protected in his South Michigan Avenue mansion. It would be August 1, 1952, that he found out that he had inoperable stomach cancer. With this news, Roe came out of hiding and sent his guards away.

On August 4, he was dressed to kill and walking down South Michigan Avenue. At 10 PM, while getting into his car, someone called his name. When he turned to answer the voice, he was met with shotgun fire and died as a result of his wounds.



He was buried in a pricey $3,500-$5,000 casket and his funeral—featuring an 81-car funeral procession—was the largest in Chicago, dwarfing Jack Johnson’s from years earlier.

As for the Chicago Outfit, it took over all of the numbers operations. In an FBI wiretap, Sam Giancana—at this time, several years removed as the boss of Chicago Outfit—said “I’ll say this. Nigger or no nigger, that bastard went out like a man. He had balls. It was a f***in’ shame to kill him.” Giancana was later assassinated in 1975 some days before he was to appear before the Church Committee and speak on a supposed CIA-Mafia plot to kill President John F. Kennedy.



  • Harold Lee Rush February 19, 2018 - 10:25 am

    KINGS The True Story of Chicago’s Policy Kings and Numbers Racketeers
    An Informal History by Nathan Thompson

  • Linda Tart November 27, 2020 - 12:15 pm

    Please, read the book, Kings, to get a more accurate account of what really happened. I noticed some false information. One, Ted, did not live in a mansion, he lived in a 6 unit building, on Michigan, which still stands. Two, Ted, almost killed, Accardo, but Ed Jones stopped him. Three, the gangsters tried to take over policy once before, but the Blacks fought them off. This was during the 20’s. If you are interested in the history of policy in Chicago, read the book. It is WELL RESEARCHED.