Born in Indianapolis, Indiana, Charleston joined the Army at 15 and served in the Philippines. Returning to America, Charleston immediately began his baseball career with the Indianapolis ABC's in 1915. He served as a player and/or manager for the ABCs, the Chicago American Giants, Lincoln Stars, St. Louis Giants, Harrisburg Giants, Philadelphia Hilldales, Homestead Greys, and Pittsburgh Crawfords.
An intense, focused, intelligent man, Charleston was among the most reknowned players of his time, a tremendous power and contact hitter and one of the finest defensive center fielders of all time. His career batting average was .353 and he regularly finished among league leaders in both home runs and stolen bases. He was also known for his combative nature, getting into many brawls, including at least one memorable fight with an array of Cuban soldiers.
In 1932, Charleston became player-manager of the Pittsburgh Crawfords and presided over perhaps the best Negro League team of all time. His roster included Hall of Famers Josh Gibson, Satchel Paige, and Judy Johnson. The team went 99-36 and Charleston himself batted .363.
In addition to his tremendous play in the Negro Leagues, Charleston excelled in exhibition play against all-white Major League teams, batting .318 with 11 home runs in 53 games. Contemporary observers compared his play to that of Tris Speaker and Babe Ruth. Baseball historians generally consider him one of the greatest players in history.
Charleston was elected to the National Baseball Hall of Fame in 1976.