Don't Expect a Derek Jeter Reunion with the Yankees Anytime Soon
About a month ago, Yankee legend - and good friend of Jimmy Sez - Derek Jeter dropped an unexpected bombshell on Major League Baseball. He was stepping down as CEO of the Miami Marlins and selling is 4% stake in the team. The timing was curious. When Jeter took over the Marlins in 2017 he immediately began clearing house in Miami. Most notably, Giancarlo Stanton was sent to New York for pennies on the dollar. It was all part of a concerted effort to rebuild the organization from the ground up. Now that it seemed he could enter the fun part of a rebuild where you actually field a quality team and win games, he decided to cash out. So what gives?
Jeter will always be a player at heart. So the ugly war waged between MLB ownership and the players' union this offseason may have had something to do with him wanting out of the ownership game. But the ultra-competitive Jeter's parting words as well as the comments of those close to him afterwards reveal the true nature of his departure. He wanted to lead an organization that was committed to winning and it became clear that his co-owners in Miami were not.
Prior to the lockout, the Marlins were active in making moves this winter. Jeter had spent his first few years on the job opening up new revenue streams for the franchise via TV and naming rights deals and was beginning to finally invest some of that money back into the team. They acquired a stable of mid-level players to plug holes in the lineup while showing a commitment to Sandy Alcantara - their best young pitcher - via a five-year contract extension. Jeter saw that as a good start, and sought to make additional moves once the lockout dust settled. He even had buy-in from the rest the Marlins ownership team to spend another $15 million this March. Or at least he thought he did.
In Jeter's public statement after leaving Miami he noted that "The vision for the future of the franchise is different than the one I signed up to lead." That would suggest that the money promised before the lockout evaporated during it. This was further corroborated by Jeter's former teammate CC Sabathia who indicated that he was targeting Nick Castellanos next in free agency but couldn't get the extra funds to do so. Castellanos eventually signed with the division rival Phillies for $20 million per season. Meanwhile the Marlins settled for Jorge Soler - who despite winning a World Series ring was a below average hitter last year - for $12 million per season. He was right to be concerned about his team staying competitive.
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With Jeter free to latch on to any team he wants now, many are suggesting that the Yankees could use his services. It's not a bad thought. Baseball fans should always root for someone to run their favorite team the way Jeter was trying to run the Marlins. A more player-friendly approach is something the Yankees are sorely missing. But would he fit in with the current regime? To that answer that question, we should probably go back 12 years or so.
Following the 2010 season Jeter was a free agent looking to sign what was sure to be the last playing contract of his career. It seemed like a forgone conclusion that the Yankees would give him his final payday at something more than his market value given how much he had meant to the franchise. The merchandise sales associated with his retirement alone would likely more than make up for any reach in salary from the Yankees. However, by the fall of 2010, Hal Steinbrenner was fully entrenched as principal owner and no longer had his father's voice in his ear. Thus began some uncharacteristic penny-pinching from the Yankees who engaged in a highly unnecessary contract negotiation with one of the most iconic players in franchise history.
The negotiation obviously ended with Jeter back in pinstripes, but along the way Brian Cashman went so far as to suggest that he test the free agent market with other teams. He never entertained the thought of leaving the Yankees, so the whole process left Jeter angry, again unnecessarily. As expected, he was nothing but respectful of the organization for the balance of his career, but this isn't the type of thing someone with Jeter's competitive nature would just forget. And in case he did, he needs to look no further than the Yankees' recent handling of contract negotiations with their star players to see that nothing's changed.
Prior to the 2021 season DJ LeMahieu was due for a new contract coming off an MVP-caliber campaign and like Jeter he wasn't looking to sign anywhere but the Bronx. All the Yankees had to do was offer a reasonable salary for an MVP candidate and move along. Instead, they low-balled him and stalled their entire offseason with a drawn out negotiation that frustrated LeMahieu and nearly had him signing with the Red Sox. The Yankee front office saw this as a win because they were able to eventually retain him while shaving a few million off the average annual value of the contract, keeping their payroll under the luxury tax threshold.
The Yankee brain trust is back at it again this year with their gross mishandling of Aaron Judge's contract situation. With free agency looming after the season, the Yankees' biggest homegrown star since Derek Jeter has made two things abundantly clear: (1) He wants to remain a Yankee for the rest of his career and (2) he'd like to secure a contract extension prior to the season so that it's not a distraction. This should be a layup for the front office.
Even with his frequent injuries, Judge has been one of the best players in baseball since 2017. He's a model citizen off the field and a respected voice in the Yankee clubhouse. Yet the Yankees are hell-bent on making this difficult. They have yet to offer an extension to Judge and are even willing to take him to arbitration over his salary for the upcoming season. A process that alienated Dellin Betances and chased him cross-town in 2019. However this ends, Judge is guaranteed to be frustrated and/or angry with the Yankees just like Jeter and LeMahieu.
The precedent has been set in Yankeeland that the only priority when it comes to personnel is squeezing every last dime of savings out of every decision that needs to be made about the roster. Instead of signing Carlos Correa this year who would have filled the Yankees' glaring need at shortstop with star power, they swung a deal for Josh Donaldson and Isiah Kiner-Falefa. It was the slightly cheaper move, but improves the team only marginally. Last year they needed rotation help and shunned Marcus Stroman in favor of Corey Kluber. Predictably, Kluber was only healthy for about half the season, but hey, they saved about $7 million in the process. The Yankees are very clearly not committed to doing everything they can do to improve their roster.
To make matters worse, Hal Steinbrenner conducted a typically tone-deaf press conference two weeks ago. He spoke about the financial challenges that the Yankees need to endure and attempted to justify their reluctance to spend more on the roster. Specifically he cited the payments he makes to New York City for the bond on Yankee Stadium, which was mostly funded by taxpayers. "We can talk about our revenues, but you’ve got to pay attention to the expenses too, and we’ve got some significant ones. So it was a tough two years," he said. An interesting choice of words given that Forbes recently valued the Yankee franchise at $6 billion, a 14% increase compared to last year. Wouldn't we all love to have a "tough" year by Hal's definition.
Put it all together and the Yankees are remarkably similar to the franchise that Jeter just left due to philosophical differences. Even if he was interested in a reunion with the franchise he helped rebuild 25 years ago - a highly unlikely circumstance - the second he brought up targeting top talent to improve the roster he'd be laughed out of the room. A Yankee future with Derek Jeter back in it as a front office executive could be a wonderful thing. The current regime is just not ready for him to come back yet.
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