Roe was born in
Galliano,
Lafourche Parish,
Louisiana to a Black 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 a Black 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 the
Chicago Outfit after Jones shared a cell with
caporegime Sam Giancana in federal prison. During their incarceration together, Giancana pumped Jones for information and was amazed by how extremely profitable
illegal gambling in poor Black American neighborhoods was for the Jones brothers. After Giancana's release he received the blessing of acting boss
Tony Accardo to
extort street tax from every numbers racketeer on the South Side of Chicago. The Jones-Roe wheels were already netting over $25 million annually, by 1946 and Giancana's crew, seeking to move in, kidnapped Ed Jones and held him for a ransom that included $100,000 and a promise to hand over control of his gambling business. Roe paid the $100,000 ransom but after Jones was released, he refused to surrender his own share of the policy business. Meanwhile, the Jones brothers fled to Mexico, leaving the entire business to Roe. ==The Caifano killing and trial==