Buck O'Neil once described him as "Ty Cobb, Babe Ruth, and Tris Speaker rolled into one". Among experts, he is regarded as the best player in Negro Leagues history. During his prime, he became a legend in Cuba and one of Black America's most popular figures. Yet even among serious sports fans, Oscar Charleston is virtually unknown today.

In a long career spanning from 1915 to 1954, Charleston played against, managed, befriended, and occasionally fought men such as Lou Gehrig, Jimmie Foxx, Lefty Grove, Satchel Paige, Josh Gibson, Jesse Owens, Roy Campanella, and Branch Rickey. He displayed tremendous power, speed, and defensive instincts along with a fierce intelligence and commitment to his craft. Charleston's competitive fire sometimes brought him trouble, but more often it led to victories, championships, and profound respect.

While Charleston never played in the Major Leagues, he was a trailblazer who became the first Black man to work as a scout for a Major League team. From the mid-1920s on, he was a player manager for several clubs. In 1932, he joined the Pittsburgh Crawfords and would manage the club many consider the finest Negro League team of all time, featuring five future Hall of Famers, including himself, Cool Papa Bell, Josh Gibson, Judy Johnson, and Satchel Paige.