Charleston was the son of Tom Charleston, a Sioux Indian and construction worker, and the former Mary Jeannette Thomas.  He was raised in Indianapolis and served as a batboy for the powerful independent ABCs team, owned then by “Ran” Butler.  In 1910, at the age of fourteen, he joined the U.S. Army.

Discharged from the service in 1915, he realized his boyhood dream and joined the hometown Indianapolis ABCs, now owned by the renown C.I. Taylor and Tom Bowser.  His speed allowed him to play shallow and command outfield play.  Once teammate Dave Malarcher claimed, “Some people ask me, ‘Why are you playing so close to the right field foul line?’  What they didn’t know was that Charleston covered all three fields and my responsibility was to make sure of balls hit down the line and those in foul territory.”

Charleston’s rookie season did not pass without discord.  On a barnstorming tour in Cuba, teammate Elwood “Bingo” DeMoss and Charleston attacked umpire James Scanlon during a heated discussion on October 24.  Charleston and DeMoss were held under $1,000 bon on charges of assault and battery.  When the volatile Charleston failed to show for the court appearance, owner Tom Bowser promptly suspended him.

Charleston responded with an apologetic letter to the public, stating in part:  “the fact is that i could not overcome my temper as often times ball players can not...I consider the incident highly unwise...I am aware of the fact that some one has said they presume I am actuated by mania, but my mind teaches me to judge not, for fear you may be judged.”

Charleston was an explosively aggressive player, who ignited his peers to a higher level of play.  With an occasional stop with the Lincoln Stars of New York City, Charleston stayed with the ABCs until the middle of 1918, before joining the Chicago American Giants.  The Giants were owned by the eminent Andrew “Rube” Foster, who started the first league to survive a full season in 1920.  Foster’s Giants were loaded with quality players, so the benevolent Foster traded Charleston back to the ABCs to balance the power with the league.  The next season, Foster moved Charleston to Charley Mills’ St. Louis Giants, before returning him to the ABCs for the 1922 season.

After the season, on November 27, 1922, Charleston married the lovely Jane B. Howard from Harrisburg, Pennsylvania.  When the Giants joined the one-year-old Eastern Colored League in 1924, the Charlestons relocated to her home town.  The following year, 1925, records show that Charleston lead the Eastern Colored League with a monstrous .45 batting average.  As a player-manager, he spent four seasons with Harrisburg.  After a dismal second division finish in the first year, he lead the Giants to three consecutive second place finishes.

Economic conditions caused the Eastern Colored League to collapse.  Charleston joined the Philadelphia Hilldale Club out to Darby, Pennsylvania.  The next year, he joined the newly organized American Negro League and hit .396.

In 1930, he joined Cumberland Posey’s independent Homestead Grays in Pittsburgh.  There, he teamed with such legendary stars as Smokey Joe Williams, Vic Harris, George Scales, Josh Gibson and Judy Johnson.  This powerhouse won a grueling 10-game World Series with the Lincoln Giants, claiming rights to the eastern seaboard championship.  Charleston’s combustive energy was the power behind many championship teams.

In 1932, financier and numbers runner Gus Greenlee raided the Grays team of its top stars, grabbing Charleston, Ted page, Ted “Double Duty” Radcliffe, and Josh Gibson.  His Pittsburgh Crawfords team would eventually be stocked with five future Hall of Famers:  Charleston, Gibson, Judy Johnson, Cool Papa Bell and Satchel Paige.  Although, now advanced in age, Charleston appeared in the first three East-West All-Star classics:  1933 through 1935.  In League title over the tough New York Cubans, lead by Charleston rallied his team, smashing out three home runs in the seven-game series for the league title.

Dominican Republic dictator, Rafael Trujillo, played Greenlee’s own game by raiding Gus’s club for its prime-time players.  In 1937, he snatched up the Satchel Paige and Josh Gibson battery, eventually breaking up the team.  In 1939 the Pittsburgh team with Charleston, reorganized as the Toledo Crawfords before moving on to Indianapolis the following season.

From 1941 to 1950, Charleston managed Ed Bolden’s Philadelphia Stars team.  There, he was influential in the development of future stars like Frank Austin, Gene Benson, Bill Cash, Mahlon Duckett, James “Bus” Clarkson, and Harry “Suitcase” Simpson.

In the sunset of his career, Charleston scouted for the Brooklyn Brown Dodgers of the United States League.  This was an experimental circuit of six teams formed by Branch Rickey to indoctrinate black players for possible moves into the major leagues.  The league failed and Charleston completed his managerial career with the Indianapolis Clowns.  In 1954, his final year in pro ball, he led them to a league championship.

Charleston’s career spanned five decades.  He is among only a few who played both before the Negro leagues started and after the major leagues entertained an interest in black players.  In 1949, the Philadelphia Evening Bulletin asked the great Oscar to pick his all-time all-star team.  He chose:  Ben Taylor (1b), Bingo DeMoss (2b), John Henry “Pop” Lloyd (ss), Oliver Marcelle (3b), Cristobal Torriente (1f), Rap Dixon (cf), Martin Dihigo (rf), with Josh Gibson and Louis Santop catching.  His pitchers were Julio LeBlanc, Satchel Paige, Wilber “Bullet” Rogan, Pat Dougherty and William “Dizzy” Dismukes.

In October of 1954, Charleston suffered a stroke and lost his balance walking down a flight of stairs.  He died a few days later.  He was survived by his wife, Jane; they had no children.  He was buried in Floral Park in Indianapolis.

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