Ollie Pickering

A speedy outfielder, Ollie Pickering had three separate stints in the major leagues (1896-1897, 1901-1904, and 1907-1908) during which he fashioned a .272 batting average over nearly 900 games. A baseball “lifer,” Pickering was managing, and still sometimes playing, in the minor leagues well into his fifties.

Ollie developed a reputation for somewhat eccentric behavior. He lost $700 on a failed theatrical show1 and once had several of his prized hunting dogs living at League Park when he was playing for Cleveland.2 In addition to other baseball “firsts” credited to Pickering (which will be discussed later in the story), Ollie may have been one of the first players to use a steam bath.3

Oliver Daniel Pickering was born April 9, 1870, at Olney, a small town in Southeastern Illinois, to Emma (née Cochenour) and Joseph Pickering. His father served with the 115th Illinois Infantry during the Civil War and worked as a cooper (barrel maker). Ollie, sometimes known as Dan, grew up with a younger sister, Josephine, and a younger brother, Harry. By the time of the 1880 US Census the family had moved about 40 miles east to Vincennes, Indiana, where he would make his home for most of his life.

Nothing is known about Pickering’s childhood, but by his late teens he was playing with the Athletic Baseball Club of Vincennes.4 One report said that he signed with a team in Wheeling, West Virginia in 18905, but no evidence could be found that he ever played there. In 1891 he played with the Hack & Simon Baseball Club, a team sponsored by a local brewery.6 His entry into professional baseball happened, at least according to a story he related several years later, in this way. After writing to several managers of minor-league teams and getting no response, in the spring of 1892 Pickering hopped a freight train and rode from his Indiana home to San Antonio, Texas. Once there he tried one more inquiry, asking manager John McCloskey of the Houston club of the Texas League for advance money and a tryout. When no money was forthcoming, Pickering rode the rails to Houston, looked up McCloskey, and, after an impromptu tryout, made the team.7

On May 21 Pickering got seven singles in seven times at bat in a 20-10 Houston win over Fort Worth.8 Each hit was a bloop over the infield too shallow for the outfielders to catch. Although not acknowledged at the time, subsequently several sources have asserted that Pickering’s performance was the origin of the term “Texas Leaguer,”9  a descriptor that remains in use today.10

Later in 1892 Pickering played briefly for Fort Worth, also of the Texas League, but left the team in mid-July. The circumstances were not reported, but he returned home and played on a local team for the rest of the summer. Pickering was out of Organized Baseball for the following two seasons, 1893 and 1894. In 1894 he formed “Pickering’s Colts” in Vincennes and in June they defeated the National League’s St. Louis Browns Reserve Team.11

He was back in Texas in 1895 and again with Houston, this time a member of the Class B Texas Southern League. No records are available in Baseball-Reference, but two sources12 reported that he was batting .372 in 56 games when he left the team in July and returned to Indiana due to the illness of his wife.

Pickering married Sarah Robbins (she went by her middle name, Eleanor, for most of her life) on November 24, 1892. The couple had two children: son Joseph, born in 1893, and daughter Emma, born in 1895. When Emma married in 1912, she was recognized as the “champion girl roller skater of Indiana.”13 The previous year, 1911, Ollie’s son Joseph accidentally shot himself in the chest while out hunting rabbits near the family’s home in Vincennes. Several sources reported the young man died14 but he eventually recovered from his wounds. In fact, later he joined his sister to form a skating team that performed in vaudeville.15

Ollie signed up with the Lynchburg Hill Climbers of the Class B Virginia League in 1896 where he continued his hot hitting batting .345. One of the league’s umpires tipped off Bill McGunnigle, manager of the National League’s Louisville Colonels. In August Pickering and Lynchburg teammate Joe Dolan were sold to Louisville for a reported $1,000. The report of the transaction provided an early glimpse of his skill set noting, “Pickering is a very fast man. He is tall, strong, and raw-boned, and has the reputation of being one of the fastest baserunners in the business.” 16

He made his major-league debut on August 9 against the Reds in Cincinnati and tripled, scored a run, and stole a base in a 5-4 loss.17 Pickering was the Colonels’ regular center fielder for the rest of the 1896 season and batted .303 in 45 games.

Pickering was the Colonels’ center fielder over the first half of the 1897 season. A rookie named Honus Wagner joined the team in July and Pickering may have directly, or at least indirectly, played a role in launching the career of the Hall of Famer. In 1917 several papers ran a story asserting that in a July 19 game against Washington Pickering was ejected for “sassing” an umpire. Louisville manager Fred Clarke reportedly said, “Now I ain’t got anybody to jam into that outfield but that clumsy bow-legged rookie we just got from Paterson, N. J.”18

No evidence could be found that Pickering was ejected from the July 19 game. Wagner made his major-league debut in center field the following day, July 20, but the more plausible reason for the switch was that Pickering was mired in a season-long batting slump. A week later it was announced that Louisville had sold Pickering to Syracuse of the Eastern League. Another reason for Pickering’s departure was because he “…does not like some of the officials in the Louisville Club,”19 a possible reference to Colonel owner Barney Dreyfuss.

Patsy Tebeau, manager of the Cleveland Spiders, refused to waive the claim on Pickering, so when the sale to Syracuse was nullified, Louisville released him outright and he was signed by Cleveland. Tebeau was in dire need of an outfielder as he had recently suspended Louis Sockalexis for drunken behavior. Pickering was the Spiders’ regular right fielder for the rest of the 1897 season and batted .352 in 46 games.

Cleveland outfielders Harry Blake and Jimmy McAleer missed most of the 1897 season. When both returned in 1898 along with incumbent left fielder Jesse Burkett, there was no room for Pickering in a crowded Spider outfield. In May Cleveland optioned him to Omaha (the franchise relocated to St. Joseph, Missouri, in July) of the Western League.20 After the season Buffalo replaced Omaha/St. Joseph in the Western League, and Pickering was one of the players awarded to Buffalo.

Pickering, however, claimed that Buffalo did not send him a contract by the March 1, 1899, deadline, and so was free to sign elsewhere.21 He then signed with another Western League team, Indianapolis. When Buffalo manager Billy Nash produced evidence that Pickering’s contract had been mailed February 27, National League President Nick Young awarded Pickering to Buffalo.22 His tenure with the Bisons was short, however; the club soon traded him to Columbus for Jack Crooks.23

He played one season in Columbus and was drafted by the Cleveland Lake Shores of the American League (then still a minor circuit) in March 1900. Pickering had a strong season, batting .324 in 140 games. He was being counted on as one of the core members of the team in 1901 when the Cleveland franchise was renamed the Blues. He was the Cleveland’s starting center fielder and leadoff man on Opening Day, April 24, 1901, at South Side Park in Chicago. Facing the White Stockings Roy Patterson, Pickering lifted an easy fly ball to center fielder William “Dummy” Hoy. Pickering’s first inning at bat in an eventual 8-2 Chicago win, made him the first batter in major American League history.24  In 1951, 81-year-old Pickering flew to Boston to commemorate the American League’s 50th anniversary.

Used primarily in center field (he also played 25 games in right field) in 1901, Pickering batted .309 and stole 36 bases for Cleveland. Possessing great speed and a strong throwing arm, he led all AL outfielders in putouts (315) and double plays turned (9). After the season he was invited to be a part of an All-American team of AL and NL stars organized by Joe Cantillon that toured the West Coast.

Pickering returned to the Cleveland club, this year named the Bronchos, in 1902. He was leading the American League with 22 stolen bases when he sustained an ankle injury in mid-July. He was slow to heal and return to the lineup and was limited to 69 games in the injury-plagued season.

He and Cleveland could not agree on contract terms for 1903. During the war between the upstart American League and established National League, Pickering was one of many players who listened to competing offers from both leagues. He reportedly turned down an offer by James Hart of the Chicago Nationals25 and decided to stay in the American League, signing with Connie Mack’s Philadelphia Athletics for 1903.

Showing no ill effects from the previous season’s injury, Pickering had a strong season for the Athletics. On June 12, facing his former Cleveland team, Pickering homered in the bottom of the 16th inning off of Addie Joss to give Rube Waddell a 2-1 win.26 His 40 stolen bases were second in the league to Cleveland’s Harry Bay and his 93 runs scored was sixth in the league. Pickering’s .969 fielding percentage was third-best among AL center fielders.

Pickering was back as Athletics’ regular center fielder in 1904. On May 5, with Philadelphia playing in Boston, he nearly spoiled Cy Young’s perfect game – twice. In the fourth inning he looped a shallow pop fly behind second base, but the Americans’ center fielder, Chick Stahl, raced in to make a running catch. In his next at-bat in the top of the sixth, Pickering hit a slow roller to shortstop Freddy Parent, whose throw nipped the speedy Pickering by a half-step at first base.27

That season, he slipped to a .226 batting average and had also begun to slow down in the field. One report noted that “…major league company had progressed while he [Pickering] had reached the limit of his speed,”28 a polite way of saying he had lost a step. Philadelphia had a younger replacement ready to take over in center field in Danny Hoffman, so that December Mack sold Pickering to the Columbus (Ohio) Senators of the Class A minor American Association.29 Pickering had two strong seasons (1905-1906) in Columbus, batting over .300 twice.

His resurgence led to a return to the major leagues. In August 1906 Pickering was purchased by the St. Louis Browns (he had played with current Browns manager Jimmy McAleer in Cleveland).30 Pickering was pleased with his second chance, saying “In St. Louis I will get a new start and I am convinced that I am better today than I ever was. Furthermore, I am older and know more about taking care of myself.”31 With Charlie Hemphill the regular center fielder in St. Louis, Pickering moved to right and got off to a hot start to the 1907 season. He was leading the American League in batting by late May32 before cooling off to .276 by season’s end.

That winter St. Louis traded him to the Washington Nationals (his fourth American League team) for outfielder Charlie Jones.33 Pickering got off to a hot start with this new team, but during an April 18 game against New York he was beaned by the Highlanders left-hander Doc Newton.34 Diagnosed with a concussion, he returned to the lineup within a week, but managed just a .225 average for the season, playing both right and center field for the Nationals.

That winter Washington sold Pickering to Minneapolis of the American Association,35 finally concluding, at age 38, his major-league career. In 886 games with five teams, Pickering batted .272 (910-for-3,352) with 500 runs scored and 194 stolen bases. His career defensive statistics are incomplete, but Pickering played more than 800 games in the field, most of them (468) in center field. He recorded 109 outfield assists and 49 errors for a career .949 fielding percentage. Applying modern metrics, his fielding percentage and range factor were slightly higher than league average.

Pickering remained at the Class A level with Minneapolis, Jersey City, Louisville, and Omaha over the next three seasons (1909-1911). Clearly hanging on, the only press coverage that he received was when he was recognized as the Western Association’s oldest player when he turned 41 while playing for Omaha in 1911.

Pickering was released by Omaha in May 1911, but in June he signed with his hometown Vincennes Hosiers of the Class D KITTY (Kentucky-Illinois-Tennessee) League. An injury cut his season short and effectively ended his career as an everyday player. Pickering then turned his attention to managing (while still playing when healthy enough). In August, he signed on with Paducah, Kentucky, also of the KITTY League.36 In last place when he took over, the Indians won 26 of their last 35 games to finish in third in the league.37

Unable to agree on contract terms with Paducah management, Pickering played briefly with Terre Haute (Indiana) club of the Central League early in 1912. The following year, however, he was back in the KITTY League as a player-manager. No records are available, but when he left Vincennes to take the job at Henderson (Kentucky), he was batting .377.38 In 1914, while with Owensboro (Kentucky) the 45-year-old Pickering, by then a grandfather of two, batted .273 with 37 stolen bases. The following year, 1915, Pickering managed, and still at times played for, Winnipeg and St. Boniface (Manitoba) of the Class C Northern League.

Pickering then announced one of his many “retirements” and worked an offseason job as a bartender in Vincennes. However, simply stating “I couldn’t stay away,”39 Ollie managed independent teams in Minnesota in 1916, and the following year organized and managed a semipro team in his hometown. He was back in Organized Baseball with a stint with Redfield of the Class D South Dakota League in 1921 and wound up his professional career back in Paducah in 1922. Signed exclusively as a manager, his name still occasionally appeared in box scores as a pinch runner and center fielder. Pickering was let go in mid-June when the club needed a full-time player manager. Pickering explained, “The club officers wanted me to play regularly,” and after more than 30 years in professional baseball he finally admitted, “I am too old to play.”40

The restless Pickering continued with independent teams in Vincennes. In the early 1930 he organized and ran the “All American Baseball School,”41 a training academy for youths age 16 and older. Active into his sixties, Pickering once played in old-timers game at age 77.

He loved to entertain visitors and reminisce about his playing days, one of whom was Baseball Commissioner Happy Chandler, who remembered watching Pickering play in his home state of Kentucky. Interviewed in 1942 at the age of 72, Pickering was asked what pitchers he faced that threw the fastest balls. He replied, “Amos Rusie, Rube Waddell, Walter Johnson, and this kid playing in Cleveland – what’s his name – [Bob] Feller.”42

When Ollie and his wife Eleanor celebrated their 50th wedding anniversary in 1942, he received a congratulatory telegram from his old manager Connie Mack. Eleanor passed away two years later, and Ollie died of a heart attack on January 20, 1952, at Vincennes at the age of 81. He was buried alongside his wife at Fairview Cemetery in his hometown. Ollie was survived by a brother, a sister, his two children, four grandchildren, and 10 great-grandchildren. One of Pickering’s great-grandchildren is current (as of 2025) National Football League official Jimmy Russell.

Acknowledgments

This biography was reviewed by Bill Lamb and Kim Juhase and fact-checked by Dan Schoenholz.

Photo credit: Ollie Pickering, SABR-Rucker Archive.

Sources

Unless otherwise noted, statistics from Pickering’s playing career are taken from Baseball-Reference.com and genealogical and family history was obtained from Ancestry.com. The author also used information from clippings in Pickering’s file at the National Baseball Hall of Fame.

Notes

1 “Ollie Pickering Lost $700 In Effort to Elevate the Stage,” Louisville Courier, July 5, 1908: 30.

2 “These Are Pickering’s Treasures,” Cleveland Press, June 3, 1903: 6.

3 “Ollie Pickering Starts the Vapor Bath Craze,” Omaha Daily News, April 2, 1911: 25.

4 “Amusements,” Vincennes (Indiana) Sun-Commercial, February 11, 1890: 3.

5 “City Intelligence,” Vincennes Sun-Commercial, July 26, 1890: 3.

6 “Hack & Simon B. B. C.,” Vincennes Sun-Commercial, April 27, 1891: 3.

7 “Gossip of the Sporting World,” Detroit Free Press, October 6, 1901: 17.

8 “In Hard Luck,” Galveston Daily News, May 22, 1892: 4.

9 Texas Leaguer: Glossary. https://www.mlb.com/glossary/idioms/texas-leaguer, Paul Dickson, The Dickson Baseball Dictionary (New York: W. W. Norton & Company, 2009), 863-864. The term was first associated with Pickering in 1906, but its use even predates Pickering’s batting feat. The San Francisco Examiner (“Some More Lurid Ball,” April 18, 1892: 8) described “Texas League” hits in a game between San Jose and San Francisco a month before Pickering’s 7-7 day in Houston.

10 Several contemporary and subsequent sources cite the term “Texas Leaguer” from Pickering’s game in Houston in 1892. See “Baseball By-Plays,” The Sporting News, October 24, 1924: 4. Incidentally, Pickering kept a clipping of the box score from that game in a scrapbook which he produced for a sportswriter some sixty years later.

11 “Browns Beaten,” Vincennes Sun-Commercial, June 26, 1894: 1.

12 “Baseball Averages,” Galveston Daily News, September 22, 1892: 4, and “Players’ Averages,” Fort Worth Gazette, July 7, 1895: 3

13 “Miss Pickering, Champ Skater, A Bride Now,” Evansville (Indiana) Press, September 26, 1912: 8.

14 Cited in several sources including “Pickering Bereaved,” Sporting Life, December 16, 1911: 15.

15 “Joe Pickering Dies Tuesday in Minnesota,” Vincennes Sun-Commercial, May 13, 1964: 23.

16 “New Players Signed,” Louisville Courier-Journal, August 9, 1896: 9.

17 Play-by-play game logs are not available.

18 “John Henry Wagner Forty-Three Today,” Bucyrus (Ohio) Evening Telegraph, February 24, 1917: 6. The same story was reprinted in several other papers at the same time.  See also Ronald T. Waldo, Honus Wagner and His Pittsburgh Pirates (Jefferson, North Carolina: McFarland, 2015), 31.

19 “Outfielder Pickering Sold,” Louisville Courier-Journal, July 31, 1897: 3.

20 “Loaned Pickering to Omaha,” Cleveland Plain Dealer, May 27, 1898: 5.

21 “Here Is a Big Row,” St. Paul Globe, April 6, 1899: 6.

22 “Manager Nash Was Excited,” Buffalo Courier, April 6, 1899: 9.

23 “Plays and Players,” Pittsburgh Press, May 15, 1899: 5.

24 “Champions Win Opening Game,” Chicago Tribune, April 25, 1901: 6.

25 “Chicago After Pickering,” Cleveland Plain Dealer, July 2, 1902: 10.

26 “Blues Lost a Heart Breaker, Cleveland Plain Dealer, June 13, 1903: 6.

27 James Buckley, Perfect: The Inside Story of Baseball’s Twenty Perfect Games (Chicago: Triumph Books, 2012); “Pitcher Young a Wonder,” Boston Evening Transcript, May 6, 1904: 10, and “Cy Young Does Not Let One of the Athletics Reach First,” Philadelphia Inquirer, May 6, 1904: 10.

28 “Sporting Notes,” St. Joseph (Missouri) News-Press, February 27, 1905: 8.

29 “Columbus Buys Ollie Pickering,” Cleveland Plain Dealer, December 11, 1904: 29.

30 “Pickering To Join Browns,” St. Louis Post-Dispatch, August 19, 1906: 14.

31 “Pickering Pays St. Louis Visit, St. Louis Globe-Democrat, January 15, 1907: 13.

32 “American League Batters,” Toronto Star, May 30, 1907: 12

33 “Meeting Echoes”, Sporting Life, December 21, 1907: 5.

34 “Yankees Pull Out in Eleventh Inning,” New York Times, April 19, 1908: 33.

35 Washington manager Joe Cantillon’s brother Mike ran the Minneapolis franchise. The two brothers regularly shuffled players back and forth.

36 “New Manager for the Indians,” Paducah (Kentucky) Sun, August 18, 1911: 2.

37 “In Third Place with Henderson,” Paducah Sun, September 23, 1911: 2.

38 “Pickering Hitting Sphere .377 Clip,” Henderson (Kentucky) Morning Gleaner, June 29, 1913: 8.

39 “Lure of the Diamond Too Strong for Ollie Pickering ‘Retired,’” Princeton (Indiana) Clarion, August 8, 1921: 3.

40 “Pickering Is Given Release,” Paducah Sun, June 21, 1922: 9.

41 “Ball School to Be Held Here,” Vincennes Sun-Commercial, March 14, 1930: 1.

42 George F. Byers, “Playing the Field,” Vincennes Sun-Commercial, December 17, 1942: 13.