Could Derek Jeter Reunite With the Yankees?

Will Derek Jeter return to the Bronx in a front office role after stepping down as CEO of the Miami Marlins?

When the 2021 season officially came to a close in October, it seemed as though Derek Jeter’s tenure as CEO and shareholder of the Miami Marlins was on the brink of showing results.

Jeter, a Baseball Hall of Famer and Yankees’ legend who helped his team capture five World Series championships as their captain and shortstop from 1996 to 2014, became an executive and shareholder of the Miami Marlins in 2017 and essentially tore down and rebuilt the club in a span of four years.

At first, Jeter drew a ton of criticism for trading reigning NL MVP Giancarlo Stanton, future MVP Christian Yelich, All-Star outfielder Marcell Ozuna and All-Star catcher J.T. Realmuto. But it was clear that he had a long-term plan to turn the organization around, which was trading big-league talent in order to retool the Marlins’ farm system with top prospects, given their miniscule payroll.

With the Marlins finally looking like they are headed in the right direction, considering they have a plethora of talented young big-league position players and arms on their pitching staff, Jeter was under the impression that they’d be able to spend more money in free agency after the lockout ended in order to compete in 2022.

However, it doesn’t sound like Marlins owner Bruce Sherman was on the same page. According to Joel Sherman of The New York Post, Jeter believed that the Marlins would be spending an additional $10-15 million to upgrade their roster later in the offseason, but this plan disintegrated during the work stoppage. Additionally, The Post reported that there was a power struggle between Jeter and Sherman regarding ego, perception and the overall day-to-day business and baseball operations strategy. Additionally, Marlins general manager Kim Ng, who Jeter hired as the first-ever female GM in MLB history in November of 2020, was said to be in a power struggle of her own with Jeter’s scouting director and longtime associate, Gary Denbo.

In the end, Jeter chose to leave the Marlins as a result of different visions about the future outlook of the organization.

So, with Jeter now available, could he and the Yankees eventually reunite at some point?

No, the Yankees aren’t bringing Jeter back to serve as their stopgap shortstop this season. But if the organization wanted to do so, they could create a high-ranking position for Jeter in their front office as we speak. Although, he’d most likely want a stake in ownership which might not happen, at least not this year while general manager Brian Cashman is still under contract.

But after the 2022 season, Cashman’s contract is set to expire. And if the Yankees come up short again in the postseason (haven’t won a pennant since 2009), it could be time to consider a change.

This change would be replacing Cashman with Jeter, who just spent the last four seasons rebuilding the Marlins. During this span, Miami made the playoffs in the Covid-shortened 2020 campaign and even won a postseason series, but more importantly, they had MLB’s 11th-best pitching staff a season ago (3.96 ERA) and their farm system is ranked No. 4 in baseball ahead of the 2022 regular season, per ESPN.

They also have a number of young, budding stars at the major league level in Jazz Chisholm, Jesus Sanchez and Sandy Alcántara, who were all acquired via separate trades throughout Jeter’s time as CEO. In addition to trading for a slew of talented prospects over the years, Jeter and the Marlins bought low on first baseman Jesus Aguilar, claiming him off waivers in December of 2019, who has since bounced back in Miami.

Earlier in the offseason, the Marlins locked up their ace, Alcántara, to a five-year, $56 million extension, signed free agent corner outfielder Avisail Garcia to a four-year, $53 million deal, and traded for catcher Jacob Stallings and third baseman Joey Wendell. And MLB Network insider Jon Heyman revealed on Monday that the Marlins were in serious talks with Nick Castellanos prior to the lockout, but if they are truly done spending, this contract could be out of their post-lockout budget plans.

The Yankees could potentially bring Jeter home as Cashman’s successor in 2023, depending on how this upcoming season plays out. And if this were to happen, Jeter would no longer have to operate under a tight budget. New York will never fully rebuild, given their big market status, and Jeter oversaw a Marlins organization that drafted, acquired and developed some of the most talented young prospects in baseball. The Yankees could use that experience, and at the same time, Jeter wouldn’t have to start from scratch due to budget constraints, as opposed to during his tenure in Miami.

Jeter has experience as both the face of the Yankees and Marlins, as a player in New York, and executive in Miami. Who is to say that he wouldn’t be willing to return to the Bronx to be the poster boy for the front office in his post-playing days? If the Yankees ultimately decide not to renew Cashman’s contract following the season, it wouldn’t be the craziest idea in the world to replace him with Jeter in the future.

The one aspect that might prevent this from happening, beyond Cashman earning an extension, would be if Jeter has a chance to pursue an ownership opportunity elsewhere, which is said to be his dream. 

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