Mighty Casey Baseball Bio: Ollie Pickering

You may have heard of the term “Texas Leaguer” – a little flair or bloop single that falls just beyond the infielders and just in front of the outfielders – but you might not know where that term came from.

It’s tied to one of the early nomads of baseball history, outfielder Ollie Pickering.

Oliver Daniel Pickering was born on April 9, 1870 in Olney, Illinois to Joseph McKendree Pickering and Emma Jane (Cochenour) Pickering.  His dad was a cooper, building barrels for local wheat and grain mills.  Ollie was one of two kids – he had a sister, Josephine Elijah, who was seven years younger than he.  A fan of baseball from the first time he came in contact with the game, one thing was certain and that was he didn’t want to build barrels.  Ollie had a more adventurous and daring streak – so in 1892 he saved up all his money and used it to buy postage.  He wrote to every baseball manager he could find in the United States, included an envelope with return postage, and hoped that someone would give him a chance to try out for the team – certain that if given a chance, he’d stick.

Nobody gave him a chance, except a manager for the Houston entry in the Texas League, John J. McCloskey.

Meanwhile, Pickering learned that rival baseball clubs in San Antonio, Texas were looking for fresh talent to help resolve a local baseball rivalry.  Without a penny to his name, Pickering raced out and caught a train heading south (well, west and then south) to Texas.  He would race up alongside a slow moving train jump up along a cattle car, and then hang on for dear life.  As Ollie once told The Sporting News, “I pigged it from my home at Olney, Ill., to San Antonio, Tex., a distance of 1,600 miles, hanging to the brake rods.  They couldn’t come too fast for me in those days, and I’ve caught a train going 20 miles an hour.”

Landing in San Antonio, he once again reached out to McCloskey, using the last stamps he had.  McCloskey said he was interested – but never sent a train ticket so Pickering could get to Houston.  While waiting, Pickering played with a couple of local semi-pro teams but didn’t have enough to cover room and board, so he lived “… under a high sidewalk at San Antonio a couple of weeks waiting for a ticket.”  The season was about to start and he still hadn’t heard from the manager, so Pickering took to the rails again.  ‘McCloskey forgot to send the ticket, and two days before the season opened, I pigged it over to Houston.  These days a player won’t report without advance money, transportation, and Pullmans, but the pig train was good enough for me.”

Let’s let Ollie finish the story.

On the morning of the day the season opened, I fell off a slow freight at Houston, hunted up McCloskey and said, “I’m here.”  

He looked me over and said: “Who are you?”

I told him and he sort of gasped.  I had a crop of whiskers with clinkers in them, one shoe, and what clothes I wore were tied on with ropes and wire.  “How did you get here?”  McCloskey asked.  

“Pigged it,” I said. “Tickets don’t cut no ice with me.  I’ve come 1,800 miles looking for a job.”  

“Have you any money?” the manager wanted to know.  

“Couldn’t make the first payment on a clay pipe,” I said.  

McCloskey said he guessed I’d do.  He gave me 50 cents and told me to come out that afternoon for a trial.  He said there might be something in me, and there was.  I blew 10 cents against a barber shop and the rest for grub, and maybe I didn’t throw in a (beverage) that did me good.  With a meal inside of me and rigged up in a new uniform I felt like a horse.  Nothing could stop me.  In seven times at bat I made seven hits with men on bases, and they couldn’t put anything past me in the field.  Houston beat Galveston 30 to 1, and the town went crazy.  

When the excitement cooled down I strolled round near McCloskey and wondered out loud if I would do.  “Come here,” hs said.  He hustled me downtown, bought me a trunk, suit case, suit of clothes, shoes, underwear, shirts, collars; in fact, a whole dude outfit, and stabled me at a hotel with real beds in it.  McClosky must have spent all of $25 togging me out, and I was the white-haired boy at Houston.  I was stuck on being a ball player, and that was how I broke into the game.  And, do you know, it was weeks before I could ride in a Pullman car without holding on with both hands?

— (“Gossip of the Players”, The Sporting News, 2/15/1902: 2. and “A Ball Player’s Start – Ollie Pickering Relates His Early Experiences”, San Antonio Daily Light, 2/18/1902: 4.)

Pickering wound up hitting ,300 in the Texas League, and he must have hung around there for a while as Baseball-Reference has a record of his playing for Houston in the South Texas League in 1895, but no records for Pickering playing in organized ball between 1892 and 1895.  In 1896, he was playing closer to home – Cairo, Illinois – before being sent east to Lynchburg in the Virginia League.  There, he was signed by a scout for the Louisville Colonels and given a chance with a major league team.  In his first game, facing Cy Young, he had three hits – all little flairs into the outfield.

Between those two events – his seven-hit game for Houston consisting of little flairs just beyond the first or third baseman or his three-hit game for Louisville consisting of several short flairs to the outfield – is the tale of the term Texas Leaguer.  Having read the stories tying the term to his first game in Houston only makes sense if his hits off of Cy Young were similar – as the term itself is rather derogatory.  A real hit is a line drive or a well placed shot.  A Texas Leaguer is the type of flair or accidental bloop single a lucky minor leaguer got in a big league game.  Either way – all the stories say it started with Ollie Pickering.

With Louisville, Pickering hit .303 and stole 13 bases in 45 games.  He didn’t hit nearly as well in 1897, so Louisville replaced him with Texas League star William Nance and sent Pickering to Cleveland.  There, Pickering found his batting stroke – he hit .352 in 46 games there.  Pickering was also fast – he could run down long flies in the outfield and stole 38 bases in 1897.  At the same time, he had his own struggles.  Pickering occasionally misplayed grounders hit to him in the outfield, and was once referred to as a “Blind Bull” on the bases – reckless and not always paying attention.

Cleveland optioned Pickering back to the Western League despite hitting .352 – he played with Omaha in 1898, Columbus/Grand Rapids and Buffalo in 1899 and the new Cleveland entry in American League when Ban Johnson and his friends started the process of converting the Western League into a major league – first by changing the league’s name.  So, when the American League declared itself a major league for the 1901 season, Pickering stayed with Cleveland – where he hit .309, scored 102 runs, and stole 36 bases for the Blues.  When his batting fell back to .256 in 1902 – a season full of injuries – Cleveland shipped Pickering to Philadelphia and Connie Mack’s Athletics.  Pickering would have a fine season for Mack in 1903 – he hit .281, stole a career high 40 bases, and scored 93 runs.  A year later, Pickering struggled, he would hit just .226 for Mack, and so he was let go.

Pickering signed with Columbus in the American Association where he was a star outfielder.  In 1905 and 1906, he hit .327 and .313 with 398 combined hits in the two seasons.  After two solid seasons, he was drafted back into the major leagues by the St Louis Browns.  In 1907, Pickering hit .276 – not a horrible season considering he was now a 37-year-old outfielder.  However, he wouldn’t stay – he was traded to Washington for Charley Jones.  The New York Times suggested that Pickering fell out of favor with Browns manager Jimmy McAleer because he occasionally enjoyed a beer and was putting on weight.  “Ollie Pickering, cast off by Connie Mack of Philadelphia, and Jimmy McAleer at St. Louis because he liked pie and beer for breakfast, has at last found his way to Washington – the baseball graveyard.”  More likely, Washington manager Joe Cantillon, who knew Pickering from his westward exhibition tours, wanted a better outfielder than Charley Jones, who complained about being in Washington.

It’s hard to believe that Pickering was trouble for anyone.  From what can be gleaned from various articles, people generally liked Pickering.  He had his limitations – he liked his pitches low but struggled against left-handed pitchers, especially those who could keep pitches higher in the zone.  There’s a story Joe Cantillon used to tell about sending Pickering to scout a young lefty pitcher.  “Bring a bat,” Cantillon told Pickering.  “If you get a few good foul balls off him, leave him in the minors.”  Articles talked about his speed afield and on the bases, as well as his occasional miscues – but he was usually referred to as being a well-known and famous outfielder, almost always in a positive light.

As a guy willing to take risks and hit the road, Pickering took a chance in the 1907-1908 off-season by investing in a local theatre troupe and touring around the Midwest with them.  Performing the act “Humpty Dumpty”, the show didn’t last long – having disbanded with just enough money to pay for tickets home for the cast and crew.  Pickering said that when the show got to his birth town of Olney, he was in trouble.  “I thought,” said Pick, “that when my own folks wouldn’t come to see a show it must be pretty punk, so I gave them all carfare home.  I don’t see why it wasn’t a winner.  Had a fine show.  I got a newspaper man to write me some bills, and they were surely swell.  Here is one of them:  ‘Pickering’s Polluted Pollywogs – Picturesque, Pestilential Posers, the Perihelion Pinks of Piccadilly.’  And yet the people wouldn’t come to see my show!”

Pickering lost about $1,000 on the venture.  His son and daughter, Joe and Ozeta, easily took to the stage, though.  They did a traveling skating show and she was an actress for a number of years before returning to Vincennes, Indiana and starting a family there.

Pickering struggled on a poor Washington team in 1908 – he hit .225 with little else to show for his season.  Released at the end of the year, Ollie threatened to retire rather than get shipped back to the minors – but that wasn’t Ollie Pickering.  He was a baseball player.  For most of 1909 he played with the Minneapolis Millers – his friend and former manager, Joe Cantillon, was happy to have Pickering in the outfield.  However, he struggled with illness and injuries.  In 1910, he was traded from Minneapolis to Louisville.  Not good enough to play in the American Association – then known for being a home for fading major leaguers, he went to Omaha in the Western League for 1911, then returned to play for his hometown Vincennes, Indiana team.  As that season ended, he suffered an even greater loss – his son, Joe, was killed while hunting when his gun accidentally discharged and fired a bullet into his chest.

Over the next decade, Pickering continued to play for low level teams in Terre Haute, Henderson, Owensboro, Owatonna, St. Boniface, and even Manitoba (Canada) – where he lied about his age and told his Canadian-based ownership he was 41 (instead of 45).  Joe Cantillon said that “he looked great for fifty…”  For several years, Vincennes tried maintaining a minor league team and Pickering would be called on to manage and occasionally play.  When not managing, he played semi-professional ball, or took time out to manage a firing range and gun club.  When Indianapolis got a team in the Federal League, there were stories that Pickering was interested in being involved – even as a player if possible.  In 1920, at 50, he was playing for Redfield in the South Dakota League, and a year later he would play for the Fort Branch Studebakers.  After managing in Paducah in 1922, he finally called it good and returned home to work in the grain mills.

But baseball never left him – we’re talking about a guy who played into his 50s.  So, he opened up a baseball school in Vincennes and tried to teach the finer points of the game to kids who wanted to make a run at being a professional baseball player.  After years of chasing dreams and fly balls, his heart finally gave out on January 20, 1952, and his restless body was buried in his adopted hometown.  One assumes his soul is still looking to play a ballgame somewhere.

In addition to adding to the lexicon of baseball, Pickering left a legacy in Vincennes – a street there is named after him.  His grandson, Oliver John Russell, like Ollie – a free spirit willing to travel anywhere to follow his dream – would eventually purchase roller coasters and other kiddie rides, bringing them home and setting up a very successful Kiddieland Park in Vincennes.

Web Sources:

Ollie Pickering Page on Retrosheet.org

Ollie Pickering Pages on Baseball-Reference.com



Newspaper Articles:

Centralia Daily Sentinel, 2/17/1896 Page 2.

“Sporting Notes”, Fort Wayne News, 9/21/1900, Pg. 3

“A Ball Player’s Start – Ollie Pickering Relates His Early Experiences”, San Antonio Daily Light, 2/18/1902 Pg. 4.

“Gossip of the Players”, The Sporting News, 2/15/1902, Pg 2.

F. C. Richter. “Philadelphia Points”, Sporting Life, 10/25/ 1902, Pg. 4.

“Baseball Bunts”, Indianapolis Sun, 4/4/1904, Pg. 8.

“Baseball Notes”  Washington Post, 7/9/2014, Pg. 27.

“Milwaukee Players”, Washington Post, 8/12/1904, Pg. 27

“Gossip of the Diamond” Indianapolis Sun, 12/20/1904

“Ollie Pickering Goes Back to Minor League”, San Antonio Gazette, 3/1/1905, Pg. 3.

“Johndon Re-elected President of American League”, Sandusky Star Journal, 12/13/1907, Pg. 7.

“Baseball Gossip”, New York Times, 12/17/1907, Pg. 7.

Poseyville (IN) News, 1/10/1908, Pg 5.

“Show Was Disbanded”, Sullivan Daily Times, 1/21/1908, Pg. 1

“Pick’s Show”, Sporting Life, 2/22/1908, Pg. 7

“Baseball Notes”, Racine Daily Journal, 4/24/1908, Pg. 9.

“Short Sports”, Newark Advocate, 12/28/1908, Pg. 6.

Racine Daily Journal, 1/8/1909, Pg. 10.

“Ollie Pickering Has Unique Record”, Altanta Constitution, 1/17/1909, Pg. 27.

“When Pickering Lost a Toenail”, Des Moines Daily Register, 8/20/1909, Pg. 9.

“Omaha Signs Pickering”, Bessemer Herald, 2/4/1911, Pg. 7.

“Des Moines Gets New Outfielder”, Des Moines Daily News, 5/22/1911, Pg. 8.

“Boy Hunter Accidentally Shot”, Loogootee Sentinel, 12/8/1911, Pg. 7.

“Pickering Bereaved”, Sporting Life, 12/16/1911, Pg. 15.

“The Western League”, Sporting Life, June 10, 1911. Pg. 23.

“Texas Leaguers”, Sporting Life, April 21, 1906, Pg. 2.

“News Items Gathered From All Quarters”, Sporting Life, April 13, 1912, Pg. 5.

Huntington News Democrat, 3/22/1912, Pg. 6.

Muskogee Times Democrat, 3/29/1912, Pg. 9.

“Ball Tosser Heads Club”, Lebanon Patriot, 6/13/1912, Pg. 12.

“Baseball Notes”, Alton Evening Telegraph, 6/8/1914, Pg. 6.

“Pickering, at 41, Beats Kid Stars”, Massillon Evening Independent, 6/15/1915.

Janesville Daily Gazette, 9/13/1915, Pg. 8.

Chandler D. Richter. “Mack’s New View”, Sporting Life, 1/23/1915, Pg. 6.

“It’s Up to Albert Lea to Keep Up Reputation”, Albert Lea Evening Tribune, 9/1/1916, Pg. 6.

“Vincennes to Have Team”, Washington Democrat, 2/23/1917, Pg. 3.

“Sport Column”, Princeton Daily Democrat, 3/16/1917, Pg. 2.

“Former Big-League Star Gets New Job”, Elkhart Review, 8/5/1919, Pg. 8.

“Fort Branch to Play Haubstadt Next Sunday P.M.”, Princeton Daily Democrat, 6/24/1921, Pg. 5.

“Kitty League Rejuvenated”, Laurel Daily Leader, 4/14/1922, Pg. 1

“Sign Four Players for Vincennes New Ball Club”, Bicknell Daily News, 4/7/1923, Pg. 1.

“Caught on the Fly”, Sporting Life, 8/12/1911.  Page. 17

“Kiddieland Thrives In Town of 18,000”, The Billboard, 2/19/1955, Pg. 59, 71.


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