“Robin Hood” Teddy Roe was a gangster who ran gambling on Chicago’s Southside from the 1940s until his death in 1952. He was known for giving back to his community—particularly the poor—at the height of his power. An attitude of bucking against the larger power in Chicago’s underworld would lead to his downfall.
Legit Career and Bootlegging
Hailing from Louisiana in August 1898, Teddy Roe was the son of sharecroppers based in Little Rock, Arkansas. He developed a skill for sewing after apprenticing under a local tailor and entered the criminal world via bootlegging. Roe was able to progress in different circles since he was white passing.
After bootlegging ended, he moved on to Detroit and worked in the car industry. He later took a chance and move to Chicago to work as a tailor. It was in working as a tailor for Edward P. Jones that he became involved in the numbers game.
Teddy Roe entered the numbers game as a runner, trying to sell people on the neighborhood lottery. At this time Black people didn’t have open access to financial institutions such as the bank and numbers operators often served that role.
Throughout the 1930s, Edward and his brother managed to reel in a great chunk of cash in operating numbers. They also benefited from the protection of Chicago politicians who managed to wet their beaks as well. Roe, for his role in the operation, managed to enrich himself and also progressed to being a decision maker in the operation.
With his wealth, Roe would give money to poor Southside natives. He also made sure that people shortchanged by other operators got their money.
The success of the Jones brothers’ operation drew the attention of Paul Ricca’s Chicago Outfit. They wanted the business in its entirety and wanted Jones and Roe out. This was for good reason as by the 1940s, the operation was reeling in over $1 million a year.
Teddy Roe’s determination to hold on to the business would result in unwanted trouble for everyone involved.