Derek Jeter: ‘I don’t miss playing the game’

Derek Jeter said goodbye to the field when he retired from playing Major League Baseball in 2014, and apparently, he never looked back.

Jeter joined Colin Cowherd’s FS1 and Fox Sports Radio show Tuesday afternoon to discuss the World Series after the Los Angeles Dodgers outlasted the Toronto Blue Jays in 18 innings to win Game 3 Monday night. During the interview, Cowherd referenced Jeter’s impressive .321 batting average in the World Series, prompting the former Yankees captain to say, “That’s what you dream of.” But one thing Jeter hasn’t dreamed about since retiring is regular-season games.

“I don’t miss playing the game. I don’t. There hasn’t been a day since I retired where I’ve missed playing the game.” – Derek Jeter pic.twitter.com/ydxUxQoC6N

— Awful Announcing (@awfulannouncing) October 28, 2025

“Look, I was fortunate, I played in a lot of World Series,” Jeter said. “I played in seven World Series, man. I’ve had a lot of at-bats, but I just love it. If there’s one thing I do miss — I don’t miss playing the game. I don’t. There hasn’t been a day since I retired where I’ve missed playing the game, but if I could wake up and play in a World Series, I’d do it.”

That can’t be true. Maybe he doesn’t miss the grind of a 162-game season and all the work that went into it. But there’s no way Jeter hasn’t missed playing the game at least once in the 11 years he’s been retired.

During his debut appearance for the NBA on NBC last week, Michael Jordan addressed this same topic, making it clear he misses playing the game. And not just championship games, Jordan misses being able to feed his competitive desire by playing any game against those who are considered the best.

“I wish I could take a magic pill, put on shorts, and go out and play the game of basketball today, because that’s who I am,” Jordan told Mike Tirico. “That type of competition, that type of competitiveness is what I live for, and I miss it. I miss that aspect of playing the game of basketball.”

Jeter wasn’t Jordan, but they were often compared for their clutch performances, mental toughness, leadership, and winning tendencies. Maybe Jeter settled into retirement by telling himself he doesn’t miss playing the game. But in the last 11 years, there must have been days when Jeter thought it would be fun to feed his competitive desire by playing the game.