Derek Jeter Does Not Miss It At All

In a recent appearance on The Herd with Colin Cowherd, New York Yankees legendary shortstop Derek Jeter made clear that, despite his storied 20-season career in pinstripes, he does not miss playing baseball – at all.

Whereas it might have been more expected to hear of some sort of pangs for the sport that defined the first half of his life, Jeter defied convention and stood firm. He was adamant that at no point, ever, has he regretted his 2014 decision to retire.

“I don’t miss playing the game. I don’t,” Jeter told host Cowherd, adding that “there hasn’t been a day since I retired where I’ve missed playing the game.”

 

Defying What Most Assumed

In his eyes, it would appear that Jeter believes he did all he could, and got enough out of his playing days. It is hard to dispute that.

Across his storied Yankees career from 1995-2014, Jeter made 14 All-Star games, won five World Series championships, and win the World Series Most Valuable Player award in 2000. He was inducted into the Baseball Hall of Fame in 2020 with the joint-highest vote share ever received by a position player – tied with fellow former Yankee Ichiro Suzuki, and second all-time behind only fellow Yankees legend Mariano Rivera – and is unanimously renowned as one of the sport’s most iconic players.

Given that pedigree, one might assume that Jeter would, at least sometimes, feel a pull back onto the field. It is assumed that players usually only retire when they have to, when their bodies make them, when they lose their edge, rather than through a lack of desire. Instead, though, Jeter’s comments suggest a clean break.

In the interview, Jeter fondly referenced his World Series appearances – seven of them, in total – but said that while the memories of achievement remain meaningful, they do not generate a longing to return to the dugout. Five rings, it seems, scratched all his itches.

 

Jeter’s Retirement Movements

Despite having closed the door on his playing days more than a decade ago, Jeter is, of course, still in baseball.

Since retirement, Jeter has remained involved in the sport in other capacities. He previously held an executive role as minority owner and CEO of the Miami Marlins, and although he departed the Marlins in February 2022, Jeter has served as an MLB analyst for Fox Sports since 2023, alongside his venture capital interests.

Notably, nothing officially ties Jeter to the only ball club he ever knew any longer. His legacy is pure Yankees, of course, but in retirement, Jeter has kept a small degree of distance from the franchise he helped to build. The occasional social media post suggests that Jeter will be the next manager of the Yankees, but there has never been anything credible to it – nor any firm inclination for Jeter that management would ever be on the cards for him. By all accounts, he much prefers being a money man.

Nonetheless, Jeter’s legacy as Yankee remains untarnished; his final plate appearance, transition to retirement, and current satisfaction all speak to a clean exit rather than a forced wrap up. Nothing in Jeter’s remarks suggests regret or second-guessing, and nor should it; his career was more than a sufficient justification for the place he occupies in baseball history. The game moves on. The Yankees move on. And Derek Jeter, the player, is done – and seems to be entirely at peace with it.

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