Born in Indianapolis, Indiana, Charleston joined the Army at 15 and served in the Philippines. After returning to the United States, he immediately began his baseball career with the Indianapolis ABC's in 1915. He served as a player and/or manager for the ABCs, Chicago American Giants, Lincoln Stars, St. Louis Giants, Harrisburg Giants, Philadelphia Hilldales, Homestead Grays, and Pittsburgh Crawfords.
An intense, focused, and intelligent man, Charleston was among the most renowned 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 .348, 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 what some baseball historians consider the best Negro League team ever. 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.  Some baseball historians consider him one of the greatest players in history. He died at age 57 in Philadelphia, Pennsylvania.
Charleston was selected to the Baseball Hall of Fame posthumously in 1976. He was the 7th player chosen of the 9 men picked by the original Negro League Committee, which initially chose Satchel Paige in 1971. In 1999, he was ranked #67 on The Sporting News list of the 100 Greatest Baseball Players, one of five players so honored who played all or most of their careers in pre-1947 black leagues. He was also nominated as a finalist for the Major League Baseball All-Century Team. Baseball writer Bill James, in his The New Bill James Historical Baseball Abstract, ranked Charleston as the fourth-best player of all-time.
- baseballhalloffame.org – Hall of Fame biography page