Considered by many the greatest Negro League player of all, multi-talented Oscar Charleston was often compared with three great white contemporaries: his hitting and speedy, aggressive baserunning (and hard-sliding style) brought favorable comparison to Ty Cobb; his physique (he was barrel-chested, with spindly legs), power, and popularity, particularly with youngsters, were reminiscent of Babe Ruth; and his defensive style and skills, playing a shallow, far-ranging centerfield with a strong, accurate arm and excellent fly ball judgment, brought visions of Tris Speaker. The New York Giants‘ John McGraw, familiar with the untapped black talent available, considered the 6′ 190-lb Charleston the best and coveted him.
A native of Indianapolis, Charleston grew up serving as a batboy for the local ABC’s. At age 15, he joined the army and was stationed in the Philippines. The military gave the underage runaway the opportunity to display his abilities in track and baseball; he ran the 220-yard dash in 23 seconds and played in the otherwise all-white Manila League. Entering big-time black baseball with the ABC’s, he was a vital cog in their 1916 Black World Series triumph over the Chicago American Giants, batting .360 in seven of the 10 games played. After stints with the American Giants and New York Lincoln Stars, he rejoined Indianapolis when the Negro National League was organized in 1920.
Through 1923, the lefthanded-hitting and throwing Charleston posted a .370 batting average with the NNL ABC’s and St. Louis Giants, and in 1921 led the league in hitting (.446), triples (10), HR (14), total bases (137), slugging (.774), and stolen bases (28), finishing second with 79 hits in 50 games. From 1922 to 1925, he was player-manager for the Eastern Colored League Harrisburg Giants, and, after a second-division finish in 1924, he led them to three consecutive second-place finishes. In 1925, he batted .424. From 1928 to 1931, he hit .347 in two-year stints with the Hilldale club and the Homestead Grays. The Grays won a 10-game Eastern Championship Series from the New York Lincoln Giants in 1930.
In 1932 Gus Greenlee persuaded Charleston to manage his Pittsburgh Crawfords. Josh Gibson, Judy Johnson, and Satchel Paige joined him to give the club four future Hall of Famers. Operating independently, they went 99-36 as their 36-year-old manager batted .363, second on the club to Gibson. Often considered black baseball’s greatest team, the Crawfords became the dominant member of the tough National Negro Association, which operated from 1933 to 1936. Pittsburgh claimed the 1933 pennant, as did the Chicago American Giants, without resolution. In 1935 the Crawfords won the first NNL’s only undisputed title. In 1936 they posted the best overall record, winning the second half of the split season. A title series with the first-half champion Washington Elite Giants was never completed, though the Giants won the only game played, 2-0.
Charleston remained with the Crawfords through 1940, following them in moves to Toledo and Indianapolis. He became manager of the NNL Philadelphia Stars in 1941 and the Brooklyn Brown Dodgers when Branch Rickey formed the United States League in 1945. He was thus put in a position to scout and evaluate players for organized baseball’s integration. He managed through 1954, leading the Indianapolis Clowns to the ’54 Negro American League title, but died after the season.
Statistics so far compiled show that Charleston batted .353 lifetime. He twice led the Cuban Winter League in SB, and had 31 during the 1923-24 campaign, setting a record that stood for more than 20 years. In 53 exhibition games against white major leaguers, he hit .318 with 11 HR.
Charleston had a famous temper, and enjoyed brawling, resulting in legendary encounters with umpires, opponents, agents raiding his teams, a Ku Klux Klansman, and, on one occasion, several Cuban soldiers. As his legs gave out, he moved from centerfield to first base, yet as long as he played, he never lost his home run power, nor his meanness on the basepaths. He was sympathetic toward young players, and was protective of rookie teammates. A demanding manager who expected his players to perform as well as he did, his strength as a pilot lay in his understanding of the intricacies of the game. He was elected to the Hall of Fame by the Committee on Negro Baseball Leagues in 1976.