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Theodore L. Roe
Born August 26, 1898
Died August 4, 1952 (aged 53)
Occupation bootlegger, policy king, gangster
Spouse(s) Carrie Roe

Theodore L. "Teddy" Roe (born August 26, 1898 – died August 4, 1952) was an African-American figure in Chicago who led a large illegal gambling business. He was active in the South Side of Chicago during the 1940s and early 1950s. People called Roe "Robin Hood" because he often helped poor people in his neighborhood. He gave money and support to those in need.

Roe refused to pay "street tax" or give his business to a powerful group called the Chicago Outfit. This group was trying to take over all illegal businesses in Chicago. Roe even shot and killed a man who was sent to kill him.

Early Life and Business Beginnings

Theodore Roe was born in Galliano, Louisiana. His family were African American farmers. He grew up in Little Rock, Arkansas. As a child, he did not go to school. He learned how to sew by doing odd jobs for a tailor.

Later, he got involved in selling alcohol illegally. This was during a time when alcohol was forbidden. He became known as a clever person who could get things done. After a few years, he stopped this work. He moved to Detroit and worked in a car factory.

When he was 31, Roe moved to Chicago. He used his sewing skills to work for a tailor named Edward P. Jones. Soon after, Jones started a lottery-like game called "policy." Roe became his first "runner," which meant he sold chances to play the game.

With protection from powerful politicians, Jones's business grew very quickly. By 1930, he was making a lot of money every day. By 1938, his earnings were even higher. Roe also earned good money from the profits.

The Chicago Outfit noticed Jones and Roe's success. This group wanted to control all the illegal lottery games in Chicago. By 1946, the Jones-Roe businesses were making millions of dollars each year. The Outfit tried to take over. They kidnapped Edward Jones. They demanded a large sum of money and that Jones give up his business. Roe paid the money to get Jones back. But after Jones was freed, he decided not to give up his business. The Jones brothers then left Chicago for Mexico. This left the entire business to Teddy Roe.

The Caifano Incident and Trial

Sam Giancana, a leader in the Chicago Outfit, wanted to take over Roe's gambling operations. He ordered men to kidnap Roe. On June 19, 1951, Roe ended up killing one of the kidnappers, Fat Lenny Caifano. Caifano was a member of the Outfit and the brother of another important leader, Marshall Joseph Caifano.

The Chicago Police Department arrested Roe. They charged him with murder. The next day, detectives took Roe to court. A detective's son later said that people in the neighborhood loved Roe. They saw him as a "Robin Hood." He was respected because he would not give in to the Italian Outfit.

To keep Roe safe from the Outfit, he was heavily guarded in jail. His meals were even prepared outside the prison to prevent poisoning. On June 25, 1951, Roe faced more charges. He was accused of planning to break Illinois's anti-gambling laws.

Roe said he acted in self-defense. His lawyers also showed that the people trying to put him in jail had ties to the Outfit. This caused important evidence against Roe to be removed. Roe eventually won the case. However, he was denied bail six times before and during the trial. After winning, Roe proudly told reporters, "They'll have to kill me to take me."

Roe's "Robin Hood" Actions

In the early 1900s, "policy kings" like Roe were very important in the African American community in Chicago. They acted like banks and employers. At this time, unfair rules and money problems greatly affected African American communities across the United States. In Chicago and other big cities, the policy business brought a lot of money into poor Black neighborhoods.

Policy kings often invested their earnings into legal businesses. These included car dealerships and churches. Roe was known for running his business well. He also helped people in many ways. He paid hospital bills for new babies and funeral costs for those who had died.

Once, an older woman won money from a different, less honest gambling group. They refused to pay her. Roe and some of his men went to the group. They convinced them to give the woman her winnings. Roe was also known to walk through poor neighborhoods. He would hand out fifty-dollar bills to people who needed help.

Personal Life

Theodore L. Roe lived in Chicago with his wife, Carrie. He had family members in Dermott, Arkansas, including a brother and a sister.

Death

After Fat Lenny Caifano's death, Sam Giancana planned a month-long campaign against African American bookmakers in Chicago. Many were shot or beaten. Others left the city forever. Roe stayed in his large home on South Michigan Avenue.

On August 1, 1947, doctors told Roe he had stomach cancer. On August 4, 1952, he dressed in a suit and hat. He sat outside his home on South Michigan Avenue. Around 10:00 p.m., as he sat on his porch, he was shot. He died outside his home.

Roe had a very large funeral. His casket cost a lot of money. It was the biggest funeral for an African American in Chicago since Jack Johnson in 1946. Thousands of people lined the streets to see Roe's funeral procession, which had 81 cars. At his funeral, Minister Clarence H. Cobb said, "He was a friend of man, and he had a pure heart."

Years later, in the early 1970s, Giancana was heard on an FBI wiretap talking about Roe. He said, "I'll say this. Black or no black, that bastard went out like a man. He had balls. ....."

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