I originally developed this chronology for Oscar Charleston. But in the end, we decided not to lengthen that book further by including it, so I am happy to place it here. If anyone sees any errors, please let me know. I’m confident in saying the information given below is far more accurate than what you will (currently) find on Wikipedia.

Primary teams played for or managed in each regular season are in bold. Primary teams played for in winter leagues are in bold italics.

 

1896: Oscar McKinley Charleston born on October 14 in Indianapolis to Thomas and Mary Charleston.

1910(?): Completes the eighth grade at Indianapolis’s Public School No. 23, marking the end of his formal schooling.

1912: Enlists in the Army on March 7, claiming to be three years older than he really is. Assigned to 24th Infantry, Company B. Arrives in Philippines on May 4.

1914: Plays in first professional baseball game on February 28 as a member of the all-black 24th Infantry team, one of four clubs in Manila League. Pitches two-hit, eleven-strikeout shutout versus All-Army team on April 18. In July, pitches one-hit, ten-strikeout shutout for Cablenews-American team in integrated all-star game.

1915: Leaves Philippines on February 13. Honorably discharged from Army in March. Makes U.S. professional baseball debut on April 11 with the Indianapolis ABCs. Punches umpire Jimmy Scanlon in game against white Donie Bush All-Stars on October 24, sparking huge brawl and leading to arrest. Travels to Cuba with ABCs to play in American Series from October 30 through December 2. Fined ten dollars on December 7 for assault on Scanlon.

1916: Plays briefly for rival ABCs outfit, Jewell’s ABCs, before joining Harlem-based Lincoln Stars in May. Returns to Taylor’s ABCs on August 20. Helps ABCs win championship series–clinching victory versus Chicago American Giants on October 29. Takes job as grocery clerk after season’s end.

1917: Marries Hazel M. Grubbs on January 9. Plays for Royal Poinciana in Palm Beach, Florida, Hotel League. Registers for military draft on June 5. Plays regular season with Indianapolis ABCs. Thirteen members of former regiment hanged on December 11 for their role in Houston race riot.

1918: Separates from Hazel. Plays with Indianapolis ABCs and is present when plane crashes on Washington Park diamond prior to game on June 2. Files for divorce from Hazel on June 26. Hits two home runs in one inning in July. Drafted into Army on August 22. Sent to Camp Dodge in Johnston, Iowa, with rank of corporal. Divorce case dismissed on October 8. Selected for Colored Students Infantry Officers Training School at Camp Pike in Arkansas on October 23. Honorably discharged on December 3.

1919: Works as porter prior to start of season. Joins Rube Foster’s Chicago American Giants and establishes himself as one of sport’s superstars. Chicago Defender labels him the “greatest player in the world.” Loaned to Detroit Stars for several games. Also plays for Jewell’s ABCs in one or two postseason games. Father, Thomas, dies.

1920: Works as chauffeur in Indianapolis. Negro National League (NNL) formed on February 12. Returns to Indianapolis ABCs, with whom he tours south for spring training. Plays in inaugural NNL game on May 2 in Indianapolis. Benched by owner/manager C. I. Taylor on May 22 for “indifferent playing.” Plays for St. Louis Giants in two games versus St. Louis Cardinals in early October. Later quits ABCs, leading to public argument with Taylor. Departs Key West for Cuba on November 16 to play with Bacharach Giants in island’s American Series and Cuban League. Arrives back in Key West on December 24.

1921: Rights sold to St. Louis Giants prior to 1921 season. Files again for divorce from Hazel in March. Spends spring training touring south with Giants. Surge in power leads to his being referred to frequently as the “colored Babe Ruth.” Sister Clarissa, twenty, dies in August. Divorce from Hazel granted on September 15. Finishes season having compiled one of the best years ever seen in a major league. Doubles and triples off St. Louis Cardinals eighteen-game-winner Jesse Haines in postseason exhibition game. Arrives in Los Angeles on November 6 to play for and manage Colored All-Stars in California Winter League.

1922: Leads Colored All-Stars to 25–15–1 finish in California Winter League, impressing white press as “without a doubt the second greatest living baseball performer in the entire universe, the great Babe Ruth being his only peer.” Team defeats Bob and Irish Meusel All-Stars in seven out of eleven games in January and February. C. I. Taylor dies on February 23. Rejoins Indianapolis ABCs in spring. Hits .425 during twenty-eight-game hitting streak from June 10 through July 25. ABCs finish league year at 50–34–1, percentage points out of first. Joins St. Louis Stars for three-game October set versus barnstorming Detroit Tigers, helping Stars win series. Marries twenty-seven-year-old widow Jane Howard on November 24 in St. Louis. Leaves with Jane immediately for Cuba, joining Santa Clara club in Cuban League.

1923: Santa Clara withdraws from league in mid-January. Oscar and Janie return to Key West on January 19. Plays for Breakers in Florida Hotel League. Returns to Indianapolis ABCs at salary of $325 per month and leads depleted team to fourth-place finish. Called “the greatest all-around player in organized baseball” by the Pittsburgh Courier. Goes 5-for-10 with three home runs while playing for Detroit Stars in three-game postseason series versus St. Louis Browns. Also plays with Chicago American Giants in postseason sets versus white semipros and Detroit Tigers barnstormers. Returns to Cuba in late October to again play for Santa Clara in Cuban League.

1924: With record of 36–11, Santa Clara awarded Cuban League championship on January 13. Involved in controversial on-field fight with opposing player and soldier on January 19. Leads Santa Clara to Gran Premio Invernal championship in February. Travels back to Florida on March 1 on same ship as John McGraw. Accepts offer to play for and manage Harrisburg Giants in Eastern Colored League for 1924 season. Receives $500 as gift from fans on July 23, proclaimed as Charleston Day at Giants’ home park. Ejected from game on September 20 for attempting to punch umpire. Compiles best statistical season of career, and one of the best of all time, by slashing .405/.476/.780 and adding twenty stolen bases in fifty-four league games. Leads Giants to sweep of best-of-seven postseason series versus minor league Harrisburg Senators. Returns to Cuba to play with Almendares in Cuban League.

1925: Almendares wins Cuban League championship with 33–16 record. Plays with All-Yankees in post-league series, including February 8 game in front of Kennesaw Mountain Landis. Returns to Key West from Cuba on February 10. Plays for and manages the Harrisburg Giants. Sends uproar-causing letter to Pittsburgh Courier on June 15 challenging legitimacy of Eastern Colored League. Leads Harrisburg to 37–19 league record, second to Hilldale’s 52–15. Wins official league batting (.430) and home run (14) crowns. As member of New York Lincoln Giants, plays postseason games versus white teams in New York, including one against team featuring Lou Gehrig. Receives most votes in fan submissions for 1925 Eastern all-star team. Posts unofficial OPS+ of 232 against top competition. Completes seven-year span during which he posts an OPS+ above 200 five times, including four of the top five offensive seasons in Negro Leagues history. Returns to Cuba to play for Habana in 1925–26 Cuban League. Mother, Mary, dies on December 4.

1926: Returns to Key West from Cuba on February 17. Plays for and manages the Harrisburg Giants, now entered in both the Eastern Colored League and the integrated Interstate League, finishing fourth and third, respectively. Homers off Lefty Grove in postseason exhibition play while playing with barnstorming Hilldale Club. Also barnstorms against major leaguers with Homestead Grays. Plays winter ball for Havana Reds in Cuba in independent Triangular League, batting .404 and leading the league in hits. Also plays for Preston sugarmill team in Cuba.

1927: Returns with Janie to Key West on February 13. Flirts with jumping to Homestead Grays and Baltimore Black Sox before returning to Harrisburg Giants. Hits longest home run—465 feet—in Harrisburg’s Island Park history on June 21. Helps Baltimore Black Sox overwhelm white all-stars in postseason series. Then returns to Cuba to play with team called Cuba in 1927–28 Cuban League. Is subject of glowing profile in El Pais claiming he is better than Ty Cobb.

1928: Posts .350 average in Cuban League. Returns to Key West from Cuba on March 13. With Harrisburg Giants folding, signs with Hilldale Club. Hits game-winning three-run home run with two outs in the ninth versus Bacharach Giants on July 26. Poses in publicity photos with black heavyweight boxing champion George Godfrey. Slashes .346/.449/.605 for Hilldale, helping lead team to 35–27–1 record. Steals four bases for Baltimore Black Sox in October 14 postseason contest versus white all-star team featuring Lefty Grove on mound. Called a “legend” by columnist Rollo Wilson. Signs three-year contract to play for and manage Hilldale. Returns to Cuba on November 1 to play for Cuba club again.

1929: Hits .333 for Cuba, but club withdraws from league on January 3. Returns to Key West with Janie on January 5. Signs Martin Dihigo for Hilldale Club, generating sky-high expectations for team’s performance. Slow start leads to Bolden firing him as manager on May 16. Punches Grays owner Cum Posey in on-field fight on May 17. Brother Berl dies on May 31. Plays in postseason exhibitions with Homestead Grays. Does not go to Cuba to play winter ball for first time since the winter of 1921–22.

1930: Signs with Homestead Grays, for whom he would play first base, in February. Brother Ben gets tryout with team and plays with Grays briefly in spring before being released. Involved in scary auto accident in South during spring training. Plays in first night game to occur on a major-league diamond on July 18 versus Kansas City Monarchs. Eighteen-year-old Josh Gibson joins team a week later. Grays win ten-game series versus New York Lincoln Giants to lay claim to Negro Leagues championship. Travels to Chicago to help American Giants win three out of four postseason games versus major league all-stars. Goes with Janie to Cuba to play for Marianao in Cuban League, but civil unrest ends season early. Charlestons return to Key West on December 31. Never plays in Cuba again, ending career on island with .339 average.

1931: Plays again with the Homestead Grays. Gives Grays season-series victory over Hilldale Club rivals with game-winning two-run home run. Plays against Satchel Paige for first time on August 1. Posey calls him “the greatest first baseman of all time,” and Grover Alexander proclaims him “the best ever.” Grays report 33–18 record against major black teams and again claim championship of black baseball.

1932: Named new manager of Pittsburgh Crawfords on January 28. Helps recruit Gibson and Paige to club. Plays in official opening of Greenlee Field on April 28. Is feted by hometown fans when Crawfords play in Indianapolis on May 15. Team reports after season that he has posted .363 batting average, .457 on-base percentage, and .551 slugging percentage. Gibson, however, becomes most dangerous hitter on team.

1933: Returns to play for and manage Pittsburgh Crawfords, who play in new Negro National League formed by Greenlee. Cool Papa Bell and Judy Johnson join team. Goes 5-for-7 with three home runs in opening day doubleheader sweep of Nashville Elite Giants on April 30. Is leading vote-getter for first East-West all-star game held at Comiskey Park on September 10. Does live interview on WGN Radio on September 9. Helps Craws win league’s second-half pennant. Crawfords win league championship after American Giants forfeit championship series by not showing up for scheduled third game.

1934: Resumes post as Pittsburgh Crawfords player-manager. Manages East to 1–0 victory in East-West game on August 26. Plays in front of large crowds at Yankee Stadium on September 9 and September 30 in games that help Paige become full-fledged superstar. In latter contest, Paige strikes out eighteen and Charleston scores from third by tagging on a pop fly to the catcher. Manages Craws to three-game postseason series sweep of Dizzy Dean’s barnstorming team. Last game, on October 23, includes nasty brawl. Tells journalist he wants “more than anything else in life to help build up colored baseball.”

1935: Paige leaves Pittsburgh Crawfords to play in North Dakota. Charleston again plays first base for and manages team. Crawfords clinch first-half pennant by winning both ends of doubleheader versus Grays on July 4. Barely holds off Buck Leonard to be leading vote-getter at first base for East-West game on August 11, in which he manages West to 11–8 victory. Crawfords play New York Cubans in seven-game league championship series. Down 3–2 in series and facing three-run deficit with two outs in bottom of ninth of game six, Charleston hits three-run home run off Martin Dihigo. Craws go on to win that game and next, on September 20, to become 1935 NNL champions.

1936: Satchel Paige returns to Pittsburgh Crawfords on April 21. Charleston continues to manage team but at thirty-nine years old for first time in career is not an everyday player. Manages East to 10–2 win in East-West game on August 23, but does not play in contest. Lends name to Daily Worker initiative to end Jim Crow in major leagues. Plays for and manages Negro National League All-Stars that barnstorms in Midwest and West during and after regular season. Crawfords win second-half flag but postseason championship series is cancelled when Oscar and other players choose to barnstorm instead. NNL All-Stars play Rogers Hornsby–led team of major league barnstormers in five-game series in October. Team wins four out of five, Oscar going 4-for-10 at the plate.

1937: Pittsburgh Crawfords trade Josh Gibson to Grays in spring. Team further weakened when prior to season nine members jump to Dominican Republic to play for dictator Rafael Trujillo’s club. For first time, is not selected either to play or manage in East-West game. Posts OPS+ of just 82 as Crawfords finish in fifth place.

1938: Wrecks car carrying Greenlee on March 5, and is fortunate to walk away with minor injuries. Convinces Greenlee to traide Paige’s rights for Schoolboy Johnny Taylor. Holds open tryouts for Pittsburgh Crawfords in April. Acts as mentor to Taylor and new finds Gene Benson and Bus Clarkson. Young Craws overachieve with official 24–16 league record. Returns to East-West game as manager of East club, which loses 5–4. Planned four-team postseason playoff series fails to materialize, depriving Crawfords of chance at another championship. Finishes run as 1932–38 Pittsburgh Crawfords manager with .324 batting average and 265–197–13 record against top competition. Works in Monroe, Louisiana, over winter.

1939: Greenlee withdraws from NNL in mid-April. Crawfords franchise given to group of Toledo businessmen that includes Jesse Owens. Named manager of the new Toledo Crawfords. Still occasionally plays first base and pinch-hits. Team travels country, with games often featuring Owens racing men, motorcyles, and horses. Pretends to be much older for publicity purposes. Crawfords withdraw from NNL after first half and enter Negro American League, posting sub-.500 records in both leagues. Praised by St. Louis Cardinals manager Ray Blades as “one of the best ball players I have ever seen.”

1940: Is separated from Janie, who is listed in Harrisburg city directory without mention of her husband. Moves to Indianapolis, with intention of bringing major Negro Leagues baseball back to hometown. Buys share in Toledo Crawfords, which he continues to manage, and persuades other owners to split home games between Toledo and Indianapolis. Announces he will no longer play in league games. Barnstorms through South on tour promoted by Syd Pollock and again featuring Owens as part of festivities. Wins first home game in Indianapolis on May 26 behind pitching of young ace Johnny Wright. Called the “Negro John McCraw” by Chicago Tribune. Hank Greenberg tells black newspaperman Al Moses that Charleston could hit the ball as far and hard as anyone ever had. Team finishes in last place in NAL. Rejects offer from Effa Manley to become manager of Newark Eagles.

1941: Crawfords having folded, announces in January launch of new Indianapolis-based club called San Blas Indians. Spends spring in Florida, recruiting players. Abandons team in early June to become manager of NNL’s Philadelphia Stars. Given credit for Stars’ temporarily improved play. Files for divorce from Janie on July 24. Stars ultimately finish with 15–46 record. Dismissed from managerial post by owner Ed Bolden.

1942: Divorce case dismissed on March 31. Registers for draft on April 27. Takes job at Quartermaster Depot in south Philadelphia. Plays for and manages Depot’s integrated baseball team in city’s Industrial League.

1943: Named Industrial League’s player of the week in June. Featured in Philadelphia Tribune spread on Quartermaster Depot team in October. Attends league’s awards banquet on October 5.

1944: Begins baseball season still playing for and managing Quartermaster Depot club. Also plays for and manages team of ex–Negro Leaguers barnstorming as Cuban Yanks on weekends. Returns to Philadelphia Stars as first-base coach in late May.  Honored as one of ten best black athletes of all time in May at special banquet given at Philadelphia’s Christian Street YMCA.

1945: Formation of new black-baseball circuit, United States League, announced in February. Named manager of league’s Hilldale entry. Invited to go on USO Camp Show trip overseas but must decline. Branch Rickey meets with league representatives on April 19–20, emerging as partner in Brown Dodgers franchise to be homed at Brooklyn’s Ebbetts Field. Instead of Hilldale, becomes manager of Brooklyn Brown Dodgers. Flanks Rickey at May 7 press conference announcing league’s launch to white reporters. Employed by Rickey to help scout black players for potential signing by major-league Dodgers, in process becoming first African American to be paid to scout for major league baseball team. Is dismissed from Brown Dodgers in late June or early July in wide-ranging reorganization. Advises Rickey and scout Clyde Sukeforth on Roy Campanella and other players. Rickey tells Campanella in October 8 meeting that Charleston has backgrounded him for club. Announcement that Jackie Robinson has signed with Brooklyn Dodgers made on October 23.

1946: Becomes umpire in Negro National League.

1947: Continues to umpire for NNL. Works NNL–NAL all-star game at Polo Grounds on July 29. Signs contract on December 19 to return to Philadelphia Stars as manager.

1948: Manages Philadelphia Stars. Team finishes in fourth place in NNL with 27–29 record. NNL disbands. Helps develop Harry “Suitcase” Simpson before his sale to Cleveland Indians.

1949: With folding of NNL, Philadelphia Stars enter reorganized Negro American League’s East division. Barnstorms through South in July with Birmingham Black Barons team featuring Willie Mays. Stars complete league season with 31–38, good for fourth place (out of five teams) in division. Takes offseason job as baggage handler for Pennsylvania Railroad.

1950: Manages Philadelphia Stars in first game between two black teams at Baltimore’s Memorial Stadium on May 7. Satchel Paige joins team in July and plays with them on and off into September. Team again finishes in fourth place in NAL East with 15–28–1 record. Ed Bolden dies on September 27. Serves as honorary pallbearer at Bolden’s October 3 funeral. Control of Bolden’s share of team passes to his daughter Dr. Hilda Bolden.

1951: Former Philadelphia Stars outfielder Harry Simpson debuts with Cleveland Indians. Willie Mays compared to Oscar in July 17 column by Al Moses. Sporting News article of July 18 reveals his role in scouting for Rickey’s Dodgers. “Oscar Charleston Night” held at Indianapolis’s Victory Field on August 25. Stars finish in third place in four-team NAL East.

1952: Included in Philadelphia Tribune Charities public panel discussion of “Sports and the Negro” on January 20. NAL reduced to six teams. Confesses to Philadelphia Tribune that he gets “his biggest thrill . . . from hearing others talk of his sensational feats on the diamond.” Best outfielder, Ben Littles, killed in fatal auto accident in Oklahoma in March. Gets good look at Indianapolis Clowns’ new slugging shortstop, Henry Aaron, thanks to Philadelphia Stars barnstorming with Clowns at beginning of season. Gus Greenlee dies on July 7. Serves as coach for East in August 17 East-West game. Stars finish last in NAL at 22–38.

1953: Eddie Gottlieb announces in March that Philadelphia Stars will not field team in 1953. Finishes managerial run with Stars having helped at least thirteen players get signed by or tryouts with teams in Organized Baseball; four former Stars from Charleston era will play in majors. Declines offer to manage team in South. Appears on Malcolm Poindexter Jr.’s WHAT Radio program on April 17. Spends season out of baseball. Comes to terms in December to manage Syd Pollock’s Indianapolis Clowns in 1954.

1954: Manages Indianapolis Clowns to NAL championship. Admitted to hospital in Joplin, Missouri, on September 11. Falls down flight of stairs soon after returning to Philadelphia home and is paralyzed from navel down. Dies at Philadelphia General Hospital on October 5, at the age of fifty-seven, due to multiple myeloma. Funeral held at Indianapolis’s Mt. Paran Baptist Church on October 11. Buried at Floral Park Cemetery.

1959: Death of brother Roy, seventy-one, on August 13.

1961: Death of brother Shedrick, sixty-nine, on November 8.

1976: Inducted into National Baseball Hall of Fame on August 9. Sister Katherine accepts honor on his behalf.

1980: Death of brother Casper, eighty-two, in December.

1985: Death of sister Katherine, seventy-nine, on April 18.

1988: Death of brother Benjamin, eighty, on February 29.

1993: Death of wife Jane Charleston on October 27.