As the son of a Negro sharecropper in Gallion, La., light-skinned Theodore Roe got no schooling and was pushed into the world without a nickel. But Ted was luckier than a gallon of Fast Dice Oil. Fate led him to Little Rock, Ark., where he did odd jobs for a tailor and learned to sew. With this education, he pushed on to Chicago and went to work for a Negro tailor named Edward P. Jones. And that put Lucky Ted on the express escalator to Easy Street.

Tailor Jones switched from pantsmaking to the policy racket and made Ted Roe...