The oldest player who ever hit in a game

Little-known Charley O'Leary had a fascinating career

September 30th, 2022
Photo via Ed Wheatley, Art by Tom Forget

Charley O'Leary had a -- at the very, extremely best -- mediocre playing career. His career slash line was .226/.270/.272 and he hit just three homers in 3,232 at-bats.

But like many early-20th-century ballplayers, the Chicago native had some ridiculous things happen during his long life in the game -- including one major highlight that should make him a baseball trivia answer for all eternity. Here's his story.

An inauspicious start

Let us begin Charley O'Leary's tale with the first game of his pro career: It was with the Minor League White Stockings in 1900. Weirdly, though, O'Leary wasn't even on the team -- he was a young messenger boy who just happened to be at Chicago's stadium.

The starting shortstop, Frank Shugart, had come down with an injury and, desperate to find a quick substitute, someone pointed to Charley and said: "There is a kid who can play the infield; give him a chance." (Something that could only happen in 1900.)

O'Leary impressed in his spot start and likely would've continued on with the team, but shortly thereafter a fastball from the alligator-wrestling Rube Waddell broke his arm. O'Leary would eventually catch on in the Majors with Detroit in 1904.

As previously mentioned, the rest of O'Leary's MLB playing career wasn't too productive. His three homers were all inside-the-parkers, which is interesting, but not totally rare for the era in which he played. In the field, though, he was an early master of the hidden-ball trick -- apparently pulling off the play on numerous occasions while playing infield for the Tigers. So adept and sneaky, in fact, that one time when he did it, the Detroit Journal referred to him as "consummating a diabolical plot."

A vaudeville star?

Off the field, O'Leary paired up with teammate and "Crown Prince of Baseball" Germany Schaeffer to do vaudeville acts. They dressed as leprechauns, did stand-up skits at bars and made some terribly bad Ty Cobb jokes -- so bad that the audience threw eggs, turnips and other vegetables at them until the two were dragged off stage.

But their act was popular enough that it's said to have inspired two Metro-Goldwyn musicals, including "Take Me Out to the Ballgame," starring Gene Kelly and Frank Sinatra.

Coach O'Leary's wild time with the Yankees

After his last year playing in the Majors in 1913, O'Leary became a player-coach in the Minors and various semi-pro leagues around the country. Then he got the call of all calls: His friend Miller Huggins asked him to come coach for the New York Yankees in 1920. O'Leary served from 1920-30, overseeing three World Series titles and one of the best teams ever assembled in 1927.

At one point during his Yanks tenure, he also avoided near death with Babe Ruth: The slugger was driving O'Leary around in Philadelphia and lost control of his car. The coach was apparently ejected from his seat onto the street, but somehow only came away with minor injuries. Ruth and his group abandoned the automobile and took a train back to New York. “Sell it if you want to,” Ruth allegedly told an employee of the garage where the car was towed. “I’ll get another one when I arrive in New York.”

Years later, while still coaching for the Yankees, O'Leary -- perhaps harkening back to his hidden-ball-trick days -- pulled off an incredible prank to give his team an advantage. While coaching first, with a runner at first, the wily veteran told a young Phillies pitcher to toss the baseball over because he wanted to take a look at it. The pitcher didn't want to disobey an experienced coach, even one on the other team, so he tossed it his way. And then, well, just read the full story from the Detroit Free Press.

One final swing in 1934

There's not much written about it, unfortunately, but later in his life, while coaching for the St. Louis Browns, O'Leary came in to take an at-bat in the final game of the 1934 season ... at nearly 59 years of age. Here's more from St. Louis Browns Historical Society & Fan Club President Ed Wheatley:

"The last time Charley had stepped to the plate in a MLB game was with the St. Louis Cardinals back in 1913," Wheatley, creator of the film "A Baseball Legacy: Fans Remember the Browns," told me. "But in the sixth inning of that September 30th game, he came up as a pinch-hitter for pitcher George Blaeholder and slapped a single. It was his only hit in his only at-bat in the last 20 years and 360 days."

Nobody was or has been (or likely ever will be) older while standing in a big league batter's box. It's also the longest gap between at-bats in Major League history. Only Satchel Paige was older in a big league appearance when he pitched for the A's at the age of 59.

And not only did O'Leary get a hit, but he also hustled around the bases to score a run. What would've been a ridiculous sight in today's game -- tweeted and written about countless times -- was nothing more than a line on a box score. Wheatley surmised the reason as best he could:

"I think it was just a situation of get the season over and let the Tigers get to the World Series with the Cardinals," he said. "All beliefs were on the Tigers winning it all and who cares about the second game of a doubleheader on the last day of the season? In the end, did anyone care? And that’s why the old coach came up to bat."

Don't worry, Charley -- we care. We care.

Photo via Ed Wheatley