Established as a boys team in 1910, the Hilldales were developed by their early manager, then owner Ed Bolden to be one of the powerhouse Negro league baseball teams. They won the first three Eastern Colored League pennants beginning in 1923 and in 1925 won the second Colored World Series. Hall of Fame player Judy Johnson was a Hilldale regular for most its professional era with 12 seasons in 15 years (1918–1932). Pitcher Phil Cockrell played for Hilldale throughout those years. Oscar Charleston, Biz Mackey, Louis Santop, Chaney White, and Jesse "Nip" Winters were also important Hilldale players in the 1920s.