He played for the Knoxville Giants, Memphis Red Sox, Indianapolis ABCs/Detroit Stars, Birmingham Black Barons, Homestead Grays, Newark Eagles, and New York Cubans.

[1] Benjamin was part of the famous Grays that won nine pennants in eleven years, for which Benjamin was part of eight Negro National League pennant teams along with two Negro World Series championships in four Series appearances.

He led the league in a variety of categories over his sixteen season career.

In 1937, he led the league in walks (thirty), stolen bases (thirteen), games (52).

Benjamin was born in Montgomery, Alabama, and died in Detroit, Michigan.