Position players taking the mound always is an adventure.

Sometimes it works out (Red Sox fans likely remember Baltimore Orioles slugger Chris Davis mowing down Boston batters in 2012). More often than not, it doesn’t.

The latter was the case Wednesday night, when the Chicago White Sox were forced to hand the ball to utility infielder Leury Garcia in the 14th inning of a 6-4 loss to the Red Sox. Garcia walked two batters, gave up a go-ahead double and took the loss — not an unexpected consequence when you bring in a guy who literally has never pitched before.

But few pitching performances by position players have been more disastrous — or more memorable — than when Jose Canseco took the hill at Fenway Park on May 29, 1993.

In what ended up being a 15-1 Red Sox win, Texas Rangers manager Kevin Kennedy sent out Canseco, a former high school pitcher, to toss an inning against his former team. It didn’t turn out well. The slugger managed to record the three outs but allowed two hits, three walks and three runs in the process, saddling him with a 27.00 ERA that stuck with him for the rest of his career.

That isn’t the worst part, though. The 33 pitches Canseco threw against the Sox did such damage to his arm that he was forced to undergo Tommy John surgery less than two months later.

“I don’t feel good about it,” Kennedy later said about the decision to let one of baseball’s best hitters pitch. “I’ll take any heat you want to throw my way.”

It wouldn’t be Canseco throwing that heat, though. He played another eight seasons in the majors but never tossed another pitch.

Check out Canseco’s one day on the mound in the video below.