Theodore Roe

Teddy Roe (August 26, 1898 - August 4, 1952) was an African-American mob boss who built an illegal gambling empire in South Side, Chicago during the 1940s and 1950s. Roe earned the nickname "Robinhood" because of his philanthropy among the neighborhood poor. After refusing to pay, "street tax," to the Chicago Outfit, Roe fatally shot a made man who had been ordered to assassinate him. In retaliation, Teddy Roe was murdered by an Outfit crew commanded by Sam Giancana on August 4, 1952.

Early life and career
Theodore L. Roe was born in Galliano, Louisiana to an African American sharecropper, and raised in Little Rock, Arkansas. As a child, he received no formal education, and when he was of age, he did odd jobs for a tailor and learned how to sew. Some time after that, he got involved in bootlegging and gained a notorious reputation as a colorful racketeer who could pass for white. His career as a bootlegger ended after a few years and he moved to Detroit, where he worked in an automobile plant. When he was 31 years old, he took what he learned working for the tailor in Arkansas, and moved from Detroit to Chicago and began working for an African American tailor named Edward P. Jones. Shortly after Roe began working for Jones, Jones decided to get involved in policy and he made Roe his first “runner”, or salesman of lottery chances. Under the protection of politicians Edward Joseph Kelly and Patrick Nash, the Kelly-Nash Machine, Jones was making $2000 a day by 1930. By 1938 he had increased his earnings to $10,000 per day and Roe was pulling down nice cuts from the profits. They soon caught the attention of Al Capone and his syndicate, and they set out to take over the numbers racket in Chicago. The Jones-Roe wheels were netting over $1.2 million annually, by 1946 and the mob, seeking to move in on the Jones brothers and Roe, kidnapped Ed Jones and held him for a ransom that included $100,000 and a promise to relinquish his policy business. Ted Roe paid the $100,000 ransom but after Jones was released, he decided not to give up his share of the business. However, the Jones brothers fled to Mexico, leaving the entire business to Ted.

The Caifano killing and trial
Chicago Outfit capo, Sam Giancana, who was attempting to take over the Southside gambling operations, ordered an attempt to kidnap Ted Roe. On June 19, 1951, Ted ended up killing one of the kidnappers, Fat Lenny Caifano, who was not only a made man, but also the brother of capo Marshall Joseph Caifano.

The Chicago Police Department arrested Roe and charged him with murder. The following day, Chicago Police Detectives Ed Landis and Richard Barrett transported Roe to a court appearance. According to Detective Barrett's son, DEA agent Rick Barrett, "My Dad said the people of the neighborhood loved Roe. He was like a Robin Hood to them. Dad always said Roe was 'respected' because he refused to give in to the Italians, the Outfit. You know how they say, 'a crook with honor'? I guess that describes Roe. He was not a loudmouthed flambuoyant jerk and definitely not a murdering thug like the drug lords who took over that same neighborhood years later."

To prevent the Outfit from murdering him, Roe was placed under heavy guard at the Cook County Jail. To prevent poisoning, Roe's meals were specially prepared outside prison walls. On June 25, 1951, Roe was further charged with conspiracy to violate the Illinois State anti-gambling statute.

Roe pleaded self-defense and his defense team was also able to link prosecutors to the mob causing key evidence against Roe to be thrown out. Roe eventually beat the case, but not before being denied bail six times before and during the trial proceedings. Upon beating the case, Roe thumped his chest and exclaimed to reporters, "They'll have to kill me to take me."

Roe's "Robinhood" effect
In their heyday, policy kings were the black community's banks and employers in Chicago. In the early part of the 20th century, segregation and economic discrimination had a devastating effect on African American communities throughout the United States, and at least in Chicago and some of the other major cities in the north, the policy industry generated a lot of cash money to poor cash-starved black neighborhoods. Policy kings put a lot of their earnings into legitimate businesses such as car dealerships and even churches. Aside from running a smooth operation, Ted Roe is remembered for paying hospital bills for newborns, and funeral tabs for the deceased. On one occasion, an elderly woman who had hit the number with one of the shady gangster wheels in town, came to Roe to complain that the gang had not paid her her money for the hit. Ted and some of his boys went over to the men and persuaded them to give her her winnings. He has also been known to walk the streets of poor black neighborhoods passing out fifty dollar bills like they were bus transfers to needy people.

Personal life
Theodore L. Roe lived in Chicago with wife Carrie until his death. He also had several relatives who lived in Dermott, Arkansas in Chicot County including a brother and a sister.

Death
After Fat Lenny's murder, Sam Giancana masterminded a month long shakedown campaign against the Black bookmakers of Chicago. Dozens were shot at or blackjacked and others simply fled the city for ever. Meanwhile, Theodore Roe was holed up in his mansion on South Michigan Avenue, protected by a small army of bodyguards.

On August 1, 1952, Roe was told by doctors that he had stomach cancer and that it was inoperable. As a result, Roe stopped hiding and dismissed his bodyguards. On August 4, 1952, he dressed in a three-piece suit and hat and strolled down South Michigan Avenue. At around 10:00 p.m., as he was unlocking his car on the street outside his apartment, a voice called, "Roe!" He turned and was cut down by several shotgun blasts. He died slumped against a tree which still stands outside his former apartment at 5239 S. Michigan Ave.

Theodore Roe was laid out in a $3,500-$5,000 casket and received the biggest funeral of any Chicago African American since Jack Johnson in 1946. Thousands lined the streets to catch a glimpse of Roe's 81-car funeral procession. At Roe's funeral, Minister Clarence H. Cobb said: "He was a friend of man, and he had a pure heart."

The Outfit seized control of his policy wheels, and many felt that Theodore Roe had pushed his luck too far. That is, until his widow revealed a secret. Lucky Ted had terminal cancer, and had been given only months to live.

Over an FBI wiretap during the early 1970s, Giancana said of Roe, "I'll say this. Nigger or no nigger, that bastard went out like a man. He had balls. It was a fuckin' shame to kill him."