What Would the Boss Do This Offseason?

By Cary Greene

November 10, 2025

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Facing the inevitable, I fear I’m going to be very disappointed yet again this offseason by whatever plan Hal Steinbrenner authorizes Brian Cashman to take this offseason. Somehow, I just don’t have much faith that Hal Steinbrenner is the right leader to bring a ticker tape parade to Manhattan any time soon and this set me to thinking. What if George Steinbrenner were still alive today, what approach would he take to this offseason?

We all know one thing, George Steinbrenner valued winning championships above all else - so what kind of plan would he set in motion in order to restore the Yankees to being champions? Well, the first thing “the Boss” would realize is that, up to now, his son has been squandering Aaron Judge’s peak years. Therefore, the buck would stop at the Boss’s desk. This would not be tolerated going forward, as the Boss’s goal is to win championships and not to merely make the playoffs.

Easily fed up with players he perceived as not rising to challenge in the postseason. One such example was how he once derided Dave Winfield as being, “Mr. May,” in contrast to Mr. October - Reggie Jackson. This was due to Winfield’s poor performance in the 1981 World Series, in which Winfield went 1 for 22 as the Yankees lost to the Dodgers that year, four games to two. There was much more to George’s dislike of Winfield and I won’t get into all of the other sordid details in today’s article. Instead, let’s imagine what moves George would make this offseason to restore his beloved Yankees to glory.

Because I don’t believe George’s son Hal will act decisively this offseason to bring a championship to the Big Apple, I’m left wondering how George would have tackled this offseason.

There is no doubt that George valued left-handed sluggers above all else, so his first move would be a rather obvious one. Aaron Boone and Brian Cashman would both be looking for work as George would loudly and vehemently fire both of them. In the blink of an eye, Derek Jeter would become the Yankees new General Manager and then George would very likely hire an older, more experienced manager – one he could fire at any point if he thought they weren’t doing a good job. Enter Bruce Bochy, he’s exactly the type George would like. He’s won, he’s got some experience, he can also blow bubbles like current Yankees manager Aaron Boone (only Bochy actually won a bubble blowing contest in the 70’s, so he’s even better at this than Boone is).

George’s next move would be to rip into the current roster and gut it accordingly. After expressing public frustration with several Yankees who performed poorly in this year’s postseason loss to the Blue Jays, George would say good riddance to Trent Grisham (2-17 vs Toronto in the ALDS), Cody Bellinger (3-16), Giancarlo Stanton (4-16), Anthony Volpe (1-15), Austin Wells (2-9).

Though Jazz Chisholm went only 2-14 in the ALCS, Jeter would lobby for the Boss to stick with Chisholm, due to his near perfect fit in New York. Of course, Grisham would be non-tendered. Bellinger would be free to seek employment elsewhere and Volpe and Wells would both be traded away.

Deciding what to do with Stanton would be next on George’s list. Stanton’s season was once again marred by missing time due to injuries. George would likely become agitated by Stanton’s inability to stay healthy and ultimately, it would be decreed that if Stanton wouldn’t accept a trade, George would simply decide to DFA him. “Enough!” George would bellow! With that command issued, Stanton’s career as a Yankee would come to an end - one way or another! 

Chisholm, still young and athletic, would be viewed by Jeter as another matter entirely, a necessary piece for 2026 and beyond and George would listen here, as he would recall the impact that Willie Randolph had on Yankees teams of the 1970’s! Therefore, the Yankees would embrace Jazz, with the good and the bad considered. George would extend Jazz and lock him up ahead of the Collective Bargaining reset. Jazz would be given a long term contract that made sense for both parties.

With all of the dead weight removed, George would set his sights on signing some free agent talent to replace the “Mr. Mays” that plagued Brian Cashman’s attempt at building a roster. George covets left handed Reggie Jackson types obviously, so his first massive signing would be none other than Kyle Schwarber. “Schwaba to the Yankees," the headlines would read. With a lightning fast left-handed bat slotting in behind Yankees future Hall of Famer Aaron Judge, the Yankees would have their number three and clean up hitters all set – and NO! George wouldn’t like the idea of his top RBI players batting two-three in the lineup, that’s not the way George rolls!

Then he's grab the big hitter from across town to play first base - Pete Alonso.

In fact, since this is what Michael Fishman would likely try to recommend to Derek Jeter, George would send Fishman and his whole analytics team packing. He’d stomp on all of their i-pads too, just for effect. There would even be a press conference where George would be filmed jumping up and down on the i-pads and kicking them out of the 5th floor windows in his office.

Some of the i-pads would even be set on fire by the new Director of Analytics, Mike “the Pope” Francesa! George doesn’t play that way, you see, oh no! We’re turning back the clock a bit here folks. No analytics allowed! LOL George would insist on advice, the right advice, and depending on the temperature - the Pope would give plenty of it! More than George would likely even be able to stand, but he’d at least listen to the sound of sanity!

Like a lightning strike, George would next sign Bo Bichette to play shortstop for the Yankees. George loved big-game players, guys who could rise to the occasion and Bichette pretty much epitomizes this and a whole lot more, offensively speaking. If healthy, Bo is also a playable shortstop, though he’s a well below average defender. Bichette is a player George would build a team around. Consider a deal done!

In a shocking move, George would then instruct Jeter to trade Ryan McMahon. Though McMahon is a superior defensive third baseman, the Boss would prefer to sign Alex Bregman to play the position long term. McMahon is projected to post a 91 wRC+ by FanGraphs and that type of production is not reminiscent of the production that Yankees legend Graig Nettles delivered during his time with the Yankees. Therefore, the Boss would prefer Bregman for obvious reasons.

Bregman meanwhile, is projected to deliver a 119 wRC+ (again, by FanGraphs) and George would heed Jeter’s advice, that Bregman would slot in perfectly in between the Yankees new first baseman and their catcher, Ben Rice!

That’s right, the Boss would trade Austin Wells and others for the best available starting pitcher that Jeter could muster to trade for.

Due to his affinity towards speedy leadoff hitters and based on Jeter’s input, George would agree that Jose Caballero has a place on the team – ala being the type of player that “Mick the Quick” Rivers was to the Yankees teams of the 70’s. With Caby’s spot on the roster locked up, George would scour the rest of the roster. Who would he like and who wouldn’t he want  on the Yankees bench – that would be next on his to-do list!

Next, the Boss would prioritize a switch hitting catcher, named Victor Caratini, who was formerly with the Astros and who would be a very sublime signing to supplement Ben Rice. With this strategy, the Yankees would look to prioritize offense over defense and while this is true, the combination of Rice and Caratini would provide a fearsome one-two punch at catcher.

In another kind of surprising move, the Boss would bring back Miguel Andujar in a bench role. Miggy, once a fan favorite in the Bronx, would provide a potent bat off the bench and he’d play some left field, some DH and some third base (in a pinch) for the Yankees. Primarily, he’d be a right handed bat off the bench and he’d serve as a pinch hitter for Bochy to use based on match ups during games. With Caballero and Cabrera coming off the bench, adding Miggy as a final bench piece would be a low cost, high ceiling move by the Boss!

Next, the Boss would lay out a rough draft of the lineup. It would look like this:

1.     Bichette - SS

2.    Chisholm - 2B

3.    Judge - RF

4.    Schwarber - DH

5.    Alonso - 1B

6.    Bregman - 3B

7.    Rice - C

8.    Jones - OF

9.    Dominguez - OF

Bench: Caballero UIF, Caratini C, Cabrera UIF/UOF, Andujar (UIF/UOF)

Would the Boss deliver a championship with this lineup? Personally I think the Yankees pitching would determine that and the Boss would throw his weight around in that department as well.

In an absolutely divisive move, the Boss would sign none other than Trevor Bauer, to a minor league deal. Yes, you read that right. Gerrit Cole and Bauer on the same team again, just like back in their good old UCLA days, when they both hated each other. You see, the Boss is about winning, not necessarily about making the club house a harmonious environment where Aaron Boone can coddle his players and pacify the New York media.

The Boss has other plans entirely. Spending on Bichette, Schwarber, Alonso, and Bregman would break even the Boss’s bank, so signing Bauer would be a high-risk, high reward type of move that a leader like the Boss would embrace. Jeter however, he would advise against such a move.

Therefore, the Boss would, as I mentioned, trade Wells and whomever else not named Dominguez or Jones, for the best available starter that they could acquire. Then, signing former Yankee Mike King would further bolster the starting pitching and the Boss would be almost done with an offseason that would rock the ages.

In his last flurry of moves, the Boss would sign Phil Maton and Robert Suarez to uplift the Yankees bullpen. With these moves, the Boss would make the Yankees instant and prohibitive favorites to win the World Series and he’d restore the baseball universe to the way things ought to be like. The mighty Dodgers would certainly have their hands full, come the 2026 World Series.