What Should the Yankees Offseason Look Like? Part 2 of 2:

What Should the Yankees Offseason Look Like?

By Cary Greene

Part 2 - Positional Breakdown

November 1, 2025

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The Yankees were plenty good offensively last season, but it will be very hard to replace both Trent Grisham and Cody Bellinger. Both would be costly to bring back and Hal Steinbrenner absolutely has a number in mind - a number that Brian Cashman shall not pass! (Lord of the Rings fan here)

Kyle Pagan from crossingbroad.com (a Phillies blog) recently and rather aggressively put it when defending whether or not the Phillies would trade Bryce Harper (as Joel Sherman of the Post recently and speculatively suggested – “Too bad George is dead and his son has alligator arms when the bill comes. This ain’t your daddy’s Yankees anymore.”

I’ll admit that I’m even guilty of coining the term Steinbrenneromics over the past several seasons. Many Yankees fans want Hal Steinbrenner to spend more aggressively on free agents, but the reality is that all teams have payroll budgets, even the Yankees. Recently, Cashman stated that his job this offseason, once internal meetings are held, will be to go out and try ti improve the team while working within whatever budget he’s given.

Cashman has also said in the past (paraphrasing here) that he’s free to bring very important things to Hal Steinbrenner, who in turn might agree to spend unplanned upon payroll dollars, providing the idea made sense. Hal Steinbrenner is the one who’s writing the checks each offseason, even if some folks (including Pagan above) accuse him of having alligator arms - unlike his father George.

I very much doubt Hal Steinbrenner would deliberately go beyond whatever the Dodgers wind up spending this offseason, but what if he did?

Our fearless commandant Paul penned a plan last week in which he advocates increasing the 2026 payroll from $256 million by $136 million (not even including taxes). Would Hal Steinbrenner approve a budget of $425 million or more for 2026? I doubt this very much.

While I love Paul’s list of free agents that he’s identified, there is no timeline that exists, that I know of anyways, where Hal Steinbrenner obliterates the MLB record for the highest payroll in the history of the sport. It just wouldn’t happen. Folks, I’m not expecting the Yankees to even have the highest payroll in MLB for the 2026 season.

Presently, the Yankees payroll sits at $230,573,333, that’s with Aaron Hicks and DJ LeMahieu factored in. If we add projected pre-arbitration and projected arbitration contracts to the payroll and also add projected competitive balance taxes to this figure, the Yankees payroll is currently projected to be $254,523,333. Just to frame this number, if we do the same calculation for the Dodgers, their payroll is currently projected at $314,936,661 - which is $60,413,328 higher than the Yankees for 2026 and folks, these payrolls don’t factor in a single free agent signing by either team and we know both will likely spend on some key pieces this offseason.

Should Hal Steinbrenner continue to tolerate the Dodgers outspending the Yankees by a whopping $60+ million, or should Hal do as Paul suggests and go all-in-to-win!? Like I’ve suggested, I don’t think Hal will add $136 million in AAV to the 2026 payroll, as Paul suggests he should contemplate doing. It remains a mystery as to how much money Steinbrenner will authorize Brian Cashman to spend this offseason, but the answer to that question will certainly determine which players Cashman winds up targeting this winter.

My Offseason Pitching Plan

Previously, I released the pitching portion of my offseason plan. I’ve advocated that the Yankees should sign the best available left-handed starter in this year’s free agent class - none other than Framber Valdez. Doing so would likely add $34 million in AAV to next season’s payroll, not even counting the added competitive balance taxes.

Many Yankees fans are clamoring for Cashman to either trade with the Tigers for Tarik Skubal or to attempt to pry Freddy Peralta away from the Brewers. Either pitcher would likely be amazing in pinstripes, but for now I’m going to call these types of suggestions pure fantasies. I’m building my plan more based in reality and so I hope Cashman spends for Peralta while deciding to keep his key prospects. I know this plan isn’t going to be popular with those Yankees fans who have visions of sugar plum fairies and Skubal or Peralta all wrapped up in ribbons under their Christmas trees, but so be it. Bah Humbug I say!

Next, I advocated for Casman to dramatically improve the Yankees bullpen by acquiring Phil Maton. I’ve heard rumors of Maton being able to command a multi-year deal with an AAV in the neighborhood of $10+ million, such is the current market value for elite middle innings relievers with proven track records and elite stuff. Maton can be counted on to hold leads and his offspeed menagerie of curves, cutters, sweepers and sinkers are downright baffling to both left and right-handed batters alike.

Now for the cherry on top of the sundae, I’m championing the notion that Cashman should also sign Robert Suarez, who had 40 saves last season with the Padres. My thinking is pretty straightforward here. Suarez is a big upgrade over the unreliable Devin Williams. He’ll be very expensive for a 35-year-old reliever, but he’s the right-handed flamethrower the Yankees pen currently lacks.  Suarez is opting out of his remaining 2-years and $16 million, so signing the flame throwing righty will likely require 3-years, with an AAV north of $20 million.

Considering that Suarez ate nearly 70-innings last season, he does check a lot of boxes and he’d be an ideal 8th-inning set up man for the Yankees if Cashman is able to get Hal Steinbrenner to spend in this key area of team need.

There you have it! I want Steinbrenner to spend $64 million in AAV to revamp the Yankees rotation and bullpen. Caleb Ferguason is probably the best available lefty in this offseason's free agent class, so adding him also might make sense but it’s probably not financially feasible, so I’ll settle for spending a whopping $64 million to set the Yankees pitching up for success for next season and beyond.

Extending David Bednar also should be in this offseason’s plan and I hope Cashman considers doing this as well. Moving Yankees prospect Carlos Lagrange into a bullpen role might provide the Yankees with a young, Dellin Betances type and once Cole and Rodon are healthy, the Yankees could also consider moving Luis Gil to a bullpen role as well, so my whole plan sets the Yankees up nicely for several seasons to come.

My Positional Offseason Plan for the Yankees

Now let’s get down to today’s business matters, here is the positional part of my two-part plan. Keep in mind, I’ve already added at least $64 million in AAV, not even counting competitive balance taxes, to the 2026 payroll. There is a huge chance that Hal Steinbrenner would decide that’s enough money spent to make the team better. Still, I’m wondering if there might just be enough in the Yankees coffers to add a few more pieces.

I’ll lead with this: Bleacher Report is projecting that Trent Grhisham has played his way into a four-year, $72 million deal whereas Sportrac projects that if Grish does get a multi-year contract, it will be in the range of $12.1 million annually. Speculation also exists that Grisham might consider a one-year, $22 million qualifying offer from the Yankees.

Grisham fit in really well with this year’s team, far better than even the boldest projection services thought he would. He sure took full advantage of his opportunity. Grish rocked a .235/.348/.464 slash line to go with a .811 OPS, while belting 34 home runs and driving in 74 runs. Though he completely vanished when pitted against superior postseason pitching, the fact remains that he had a really good season.

Due to the Yankees' need for pitching this offseason and considering that there will be a limit to the checks on the table that Hal Steinbrenner will be able to reach, extending a qualifying offer to Grisham (while it may seem unlikely) might be something Cashman should consider bringing to Steinbrenner – but not at the expense of the Yankees needs in the rotation and the bullpen. Also, extending the QO to Grisham would have to be done before signing any free agents, so the Yankees would have to want him pretty badly if they went this direction.

Making a Run at Bellinger

Caught between a rock and a hard place between what to do with Grisham and signing Cody Bellinger, Cashman and the Yankees should focus on making a run at Bellinger. Make no mistake, Bellinger was a great fit for the Yankees last season, both on and off the field.  Everyone knows, including Cody Bellinger’s agent (Scott Boras), that signing Bellinger is extremely important to the Yankees future. Have the Yankees often been used for negotiating leverage by Boras? Absolutely. But with the current Collective Bargaining Agreement set to expire at the end of next season, who knows what kind of free agent market is going to develop this offseason, especially for big name players like Bellinger.

Bringing Bellinger back on a team friendly deal is probably not in the cards as projections regarding the contract he will receive range from 5-years and $140 million (Newsweek) to 6-years and as high as $182 million (Yahoo Sports). Could the Yankees add to the $64 million I’ve already spent? Is there room for another $30 million or so in AAV for 2026? Bellinger’s positional versatility does make him an ideal fit, especially seeing as how the Yankees are trying to remain a contender in 2026 and beyond.

How much longer will the Yankees window as a contender remain open? Can the Yankees risk not signing Bellinger? I don’t think they can go there, they kind of have to sign him. Let’s add his contract to the pot then, I’m now asking Hal Steinbrenner to spend an additional $90 million, plus CBT penalties, this offseason. Signing Bellinger also gives the Yankees some platoon flexibility at first base for when the Yankees want to sit Rice versus tough lefty starters.

Let’s back it up and acknowledge the Yankees biggest need for 2026 and beyond: the Yankees absolutely need a center fielder. This coming season, somebody has to patrol the expanse that Joe Dimaggio and Mickey Mantle used to roam for the Yankees.

Is Jasson Dominguez or Spencer Jones going to be the next in a long line of storied Yankees centerfielders? Could the Yankees pass on bringing back Bellinger while also passing on extending a qualifying offer to Grisham? I think doing this would simply be too risky. That said, any and all options are on the table for this offseason.

If Bellinger’s market explodes and he becomes uber expensive, it might motivate the Yankees initiate a youth movement and under those circumstances, there does exist a completely different way to replace - and even improve upon - Bellinger’s production.

A Trade Nobody Sees Coming

Perhaps Dominguez and Jones will both be ready at the start of the season to patrol the outfield alongside Aaron Judge. If they are, it saves the Yankees a boatload of money that could be allocated elsewhere. But where?

Encouragingly, Ben Rice has emerged at first base this past season and the good news is Rice mashes right-handed pitching. That means that he’s playable about 75% of the time against most teams. While it's true that many rival GM’s have inquired regarding Rice’s availability, the Yankees likely won’t be interested in dealing him.

While it's clear that the Yankees likely won’t be trading Ben Rice this winter, perhaps the Yankees might consider moving Austin Wells? With four full years of team control remaining, Wells is actually one of the Yankees most valuable trade assets.

With Catching being in high demand League-wide, Baseball Trade Values suggests Wells is currently worth a whopping $37.7 MTV - which ties him with George Lombard for being the second most valuable Yankee other than Aaron Judge. What if the Yankees made Rice the everyday catcher and put Wells on the market, perhaps paired with Lombard, in hopes of attracting either a front-end starter or perhaps a legitimate shortstop? It’s a question worth vetting for sure, though it does open a need at first base for the Yankees.

While he’s become a superb pitch framer, if Robo Umps take over MLB in the near future, much of what Austin Wells offers defensively kind of goes by the wayside. Maybe trading him now, while his value is very high, is a smart play for the Yankees?

Personally, I do think the Yankees should attempt to trade Wells, but my 2026 plan in no way depends upon this happening. It would be a great way to diversify the roster if he were traded, mainly because Rice’s presence makes him rather expendable. That said, he is a left-handed, power hitting catcher so with Rice entrenched 75% of the time at first base, there certainly is room for both of them in the lineup.

Tremor Alert

Tremor Alert: This year’s free agent class also includes Bo Bichette! While Bichette had a down year last season defensively, even by his well below average standards, if he’s healthy there is no reason to suspect he wouldn't rebound into the form of a playable shortstop.  He was twice as bad last year as he’s been throughout his career. He had a right-calf strain in 2024 and recently he sprained his left knee and it’s kept him out of the playoffs so far this postseason (though he will likely be ready just in time for the World Series). There is no denying that Bichette’s bat would be a massive upgrade to that of Anthony Volpe’s or any other stopgap type the Yankees will be able to muster next season.

On the open market this offseason, Bichette’s contract projections call for a seven-year deal in the $180 to $200 million range. If the Yankees were to sign Bichette,  it would be a very interesting strategy. Donte will command about $29 million in AAV so if the Yankees pivot away from Bellinger, Bichette could make sense. His splits are great against both left and right handed pitching and he’d be a very good fit in the Yankees lineup.

If healthy, Bichette would  likely get back to being minus 4 to minus 5 OAA shortstop, which means he’d be an acceptable defender at the position, given how good his bat is. No splits to worry about here folks. This guy plays every day and can hit any pitcher, regardless of said pitcher’s handedness.

In a world where the Yankees decide not to pursue Bellinger, Bichette is the perfect play and it would mean letting Jasson Dominguez and possibly even Spencer Jones take a crack at starting jobs in the Yankees outfield. As risky and experimental as it sounds, its a gamble that has a lower floor but a very high ceiling.

Barring a trade for an elite starter, there likely won’t be room in the positional portion of the Yankees budget this offseason to sign a player like Bichette while also signing Cody Bellinger. Being only 27 years-old certainly makes Bichette a player that Brian Cashman should probably consider signing. He’s hands down a vastly more productive hitter than Anthony Volpe is.

If the Yankees did trade Austin Wells (and likely others) for a top shelf starter, a plan that goes in this direction would need to provide a solution at first base. Would Spencer Jones or Jasson Dominguez be part of a mega package? Yes, this is very much a possibility.

Tsunami Warning

With Rice as a primary catcher, the Yankees would need a first baseman and a right-hand batting backup catcher. The latter would be fairly easy to conjure up on the cheap this offseason. But first base is a key position for a team like the Yankees. Don’t believe me? Look up Lou Gherig’s stats and get back to me. Real Yankees teams are built with power hitters on the corners, so I’m suggesting that if the Yankees do trade Wells for a front line starter, they should look for a power hitting first baseman and the answer is right under our noses.

Pete Alonso also happens to be a free agent this offseason. Should a bidding war occur over Alsonso, he’s projected to receive a contract of about 7-years and $210 million, while more conservative projections are calling for 5-years and $115 million and I’ve even read that he could wind up getting only 4-years and between $88 and $110 million.

If the Yankees wind up letting Bichette come off the board, jumping into Alonso’s market in the eleventh hour could turn out to be a great move. Imagine for one moment, a Yankees  lineup featuring Judge, Bellinger, Rice, Alonso and Stanton.

My Positional Plan in a Nutshell

Most Yankees fans would consider it to be a very successful offseason if Cashman could sign Valdez, Maton, and  Suarez to shore up the pitching. After the dust settled from the Yankees pivoting and deciding to execute a blockbuster trade for a top-shelf starter, the Yankees would likely need a centerfielder (assuming Jones and or Dominguez are traded).

Therefore, signing Bellinger and one of Bichette or Alsonso would reshape the Yankees roster, making them a pretty legitimate championship contender for next season.

Would a Youth Movement Work?

Getting back to the notion of the Yankees executing a youth movement, I’m wondering what the chances are of Cashman committing to such an idea. What if Cashman passes on signing a single free agent? I hope that doesn’t happen and it seems pretty unlikely. But what if Yankees fans are faced with Hal Steinbrenner backing up what he’s said in the past, when he’s threatened to reset the Yankees repeat CBT offender status?

Afterall, Hal has repeatedly said that he doesn’t think massive spending is a sustainable strategy. What if the time is now for Hal to mandate a commitment to a youth movement? Do the Yankees have enough pieces to make something like that a success?

Last winter, I was dreaming of Dominguez a bit, hoping he might be able to ascend to the top spot in the Yankees lineup at some point during the season, but Grisham’s amazing season solved that problem for the Yankees. Dominguez is still extremely young and considering his low trade value, giving up on him this offseason (by trading him) wouldn’t provide the kind of return that would make doing so worthwhile. Maybe Dominguez is the key to the Yankees offseason approach?

Granted, per StatCast, Dominguez was as bad in left field last season as the injured Bichette was, at shortstop and the eye test supports StatCast’s assessment. Though he’s got a strong arm and great footspeed, Dominguez struggles to pick the ball up and he has massive difficulty coming in on balls. That begs the question, are the Yankees playing him out of position in left field? Should they move him back to center field for the time being? Small sample sizes of advanced metrics say that he’s even worse in center field and that he’d likely bungle such a move, so the Yankees do have quite the conundrum pertaining to where to play Dominguez on their hands.

With Giancarlo Stanton doing well against both left and right-handed pitching last season, Dominguez only got 30 plate appearances as a DH, but the Martian’s role in the future certainly looks like he may be a part time outfielder who gets most of his at bats as a DH.

Meanwhile, Spencer Jones is widely considered to be a better defensive player than Dominguez is, but due to his strikeout issues, he’s probably not a viable option for the Yankees in the first-half of the coming season.

Barring something I didn’t see coming, I do think the Yankees should strongly consider having both Dominguez and Jones battle it out for outfield spots in Spring Training.

In a full on youth movement scenario, the Yankees would still field a lineup better than most teams could muster. Talk about an anti-spending approach! It would look like this:

1.     Caballero SS

2.    Jones OF

3.    Judge RF

4.    Rice 1B

5.    Stanton DH

6.    Chisholm 2B

7.    Wells C

8.    McMahon 3B

9.    Dominguez OF

The rotation would be:

1.     Fried

2.    Schlitler

3.    Gil

4.    Warren

5.    Winans or Beck with Rodriguez-Cruz as a mid-season reinforcementCole & Rodon both to return at some point

In a plan like this, the Yankees come in only $10 million over Tier 1 of the CBT. Then, they could sprinkle in a free agent here and make a trade there. The payroll would be manageable and the team would likely still be competitive. Fans love home grown teams and Yankees fans know this all too well based on the dynasty that was fueled most recently by the core four.

Flexibility is the Key

My pitching related and positional plans outlined above provides a lot of flexibility heading into what will be a very uncertain offseason. Improving the pitching needs to be the primary focus. Signing Bellinger and or one of Bichette or Alonso is on the table. A blockbuster trade should also be something Cashman explores making happen.

I’ve been forced to conclude that there likely isn’t going to be a preconceived plan that’s realistic or would be something Cashman could stick to. He’s going to need to remain ever flexible as works his offseason magic. Buckle your seatbelts Yankees fans – it’s going to be a really wild offseason.