Ollie Pickering told The Cleveland Plain Dealer in 1902 the lengths he went to get “discovered” and signed to his first professional contract 10 years earlier:
“I went bankrupt buying postage stamps. I wrote to all the managers I ever heard of asking for a job and enclosing stamps for reply. None of them answered, so I pigged it from my home in Olney, Illinois to San Antonio.”
By “pigged it” Pickering meant he jumped a freight train loaded with pigs.
“Sixteen Hundred miles hanging to the brake rods.”
Pickering said he arrived in San Antonio with one stamp left. He sent a letter to John McCloskey who was managing the Houston Mudcats. McCloskey invited him to Houston for a tryout.
Pickering “lived under a sidewalk” in San Antonio and couldn’t raise the money for a ticket, so hopped another freight train.
“These days a player won’t report without advance money, transportation and Pullmans, but the pig train was good enough for me.”
Upon arrival in Houston—Pickering said it was the first day of the season.
“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.”
Pickering said McCloskey gave him 50 cents and told him to return in the afternoon for his tryout.
“I blew 10 cents at a barber shop and the rest for grub.”
He headed to the ballpark:
“With a meal inside of me and rigged up in a new uniform I felt like a horse. Nothing could stop me.”
Pickering claimed to get seven hits, “In seven times at bat,” in the game in which he was tried out.
“When the excitement cooled down, I strolled around near McCloskey and wondered out loud if I would do. ‘Come here,’ he said. ‘He hustled me downtown, bought me a trunk, suitcase, suit of clothes, shoes, underwear, shirts, collars; in fact, a whole dude outfit and stabled me at a hotel with real beds in it.”
Pickering estimated his manager spent $25 on him.
“I was stuck on being a ballplayer, and that was how I broke into the game. And you know, it was weeks before I could ride in a Pullman car without holding on with both hands.”
How accurate Pickering’s story was is unknown, but Pickering was referred to by The Galveston Daily News within weeks of his arrival in Houston as, “Pickering, the box car artist.” Although The San Antonio Light said years later that Pickering had, “played several games,” with teams in San Antonio before meeting McCloskey in Houston—suggesting he wasn’t as down and out as related in the story.
Pickering bounced around the Southwest before making the major leagues with Louisville Colonels in 1896. He played part of eight major league seasons for six teams. He was th first batter in the American League’s inaugural game; on April 24, 1901, he led off for the Cleveland Blues against Roy Patterson and the White Sox. The Chicago Tribune said:
“Pickering was the first to face him and the first ball of the season was a ‘ball,’ but it was closely followed by a ‘strike’—an American League strike, and not the National League brand…The Pickering raised a high fly which gave (Bill ‘Dummy’) Hoy the first putout of the season.”
Baseball History Daily 
Cool story. Enjoyed it!
Thank you.