How did this woman, a Caribbean immigrant, become so successful in the numbers racket that the most notorious gangsters in New York City wanted to see her dead? For most Black women of that era, menial work was the only option. Obviously, St. Clair’s aspirations and attitude made a career as a servant an impossibility. Not much is known about her early life or even where in the Caribbean she was from, but the lasting legend of Madam Stephanie St. Clair says a lot about her time on Planet Harlem, where she controlled a large part of the uptown numbers action. And like many Black folk, regardless of their “profession,” St. Clair had clear political positions on the struggles for equality, and, frequently, wrote letters decrying oppression and police brutality. Through her pluck, savvy, and entrepreneurial genius, she became a millionaire and lived among the elite class of Harlem, some of whom were housed at 409 Edgecombe Avenue.