The Yankees are currently sitting third in the AL East with a 74–60 record, and their playoff hopes are still very much up in the air. So, for Aaron Boone, the pressure is on, as he hasn’t delivered a World Series title since taking over in 2018. And anything short of a deep postseason run could put his job in serious jeopardy.

“What happens if they miss the playoffs? Unlikely, but what happens? More likely they could get knocked out early….. Does Aaron Boone come back? Does Brian Cashman come back? Or do they finally turn the page? All of these seemingly in play,” MLB insider Ken Rosenthal hinted about the chances for a shuffle.

But if Boone is out, the big question becomes: who steps in?

One name that keeps popping up is Derek Jeter, who has Yankees fans buzzing. After all, Jeter’s resume as a player, five World Series rings, and a legacy as the face of the franchise make him an intriguing option. The popular belief is that his presence alone could spark the kind of turnaround the Yankees have been chasing. But the real question is: could Jeter actually be the one to lead them back to a championship?

“The Yankees should hire Derek Jeter as President of Baseball Operations. Like the Giants hired Buster Posey,” Yankees insider Paul shared.

Take Buster Posey as an example. The former Giants catcher has stepped into leadership with a player-first, human approach, blending analytics with instinct and a deep understanding of the franchise he helped define. That’s something Derek Jeter could potentially replicate in New York.

On top of his Yankee legacy, Jeter also brings front-office experience from his time running the Marlins between 2017 and 2022, which makes him look like a ready-made candidate to replace Aaron Boone. But there’s a catch!

Jeter’s past contract disputes with GM Brian Cashman left the relationship strained. And that history has fans questioning whether Paul’s suggestion of Jeter taking over is realistic or just wishful thinking.

Fans are wondering if Jeter could return to the Yankees

“You do realize Cashman hates him right,” one fan remarked. “Great idea. But won’t happen until Cashman decides to leave,” added another. Well, fans might be hoping to get Jeter in the Yankees’ hot seat, but will Cashman approve it?

For the unversed, Cashman and Derek Jeter saw things sour during their 2010 contract talks. The real sticking point was how they valued Jeter.

Reportedly, Cashman thought a three-year, $45 million deal was plenty, given that Jeter’s numbers were slipping. But Jeter’s side saw it differently.

They argued his legendary status meant he deserved more, even going so far as to float the idea of an ownership stake in the Yankees! While we have not seen any olive branches growing between the two, Cashman might make decisions in the team’s best interest.

But apart from Cashman, fans are also skeptical due to Jeter’s stint with the Marlins.

“He tried in Miami and it was a disaster,” one user said. “I love Jeter, but he did absolutely nothing for the Marlins,” another one remarked.

Derek Jeter, after his legendary 20-year run with the Yankees, took on a new challenge with the Marlins in September 2017, overseeing both business and baseball operations. But over four full seasons, the team went just 218-327, with one playoff run in the 2020 season. Moreover, since 2018, the Marlins have owned the worst winning percentage in the NL (.400).

“He didn’t do well at Miami. What would be different?” one user asked. So while Jeter is celebrated as a player, his track record in the front office tells a different story. But does that automatically mean he’s not destined for a future role with the Yankees?

Not necessarily. The bigger question right now is whether the Yankees are even ready to move on from Aaron Boone. And so, for now, all eyes are locked on how their playoff run plays out.