Are the Yankees Going to Repeat their 2020-21 Offseason?

Are the Yankees Going to Repeat their 2020-21 Offseason?

Frozen December Thoughts by Cary Greene

December 28, 2025

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Since I’m already on record for writing numerous times, I wouldn’t be surprised to see Hal Steinbrenner pigeonhole Yankees GM Brian Cashman into a repeat performance of the 2020-21 offseason when the Yankees brought DJ LeMahieu back on a six-year, $90 million contract, I’m sorry to report that it looks like I might be right about this.

When the 2020-2021 offseason began, LeMahieu was rated the 4th best free agent by MLB.COM that offseason. This offseason, the Yankees appear to be charting a very similar course as the team is purportedly prioritizing  signing Cody Bellinger, who happens to be ranked as the 5th best available free agent this season (behind Kyle Tucker, Alex Bregman, Kyle Schwarber and Bo Bichette)!

Spending a total of $114.45 million during the 2020-21 season, Cashman managed to reinforce the outfield (signed Brett Gardner for $5.5m) while adding one starter (signed Corey Kluber for $12m) and trading for another (Jamison Taillon). He also reinforced the bullpen with two reasonably priced high-leverage relievers (Justin Wilson $5.15m and Darren O’Day $5.15m), but the bulk of his effort was spent making many seemingly irrelevant Minor League signings in attempt to provide depth and while some of those moves Cashman made turned out to be good ones (signing Nestor Cortes Jr), many didn’t pan out (names like Jay Bruce, Derek Dietrich, Nick Goody, Socrates Brito, Adam Warren and several others).

It seems that Hal Steinbrenner will likely prefer to see the Yankees use a similar approach to the one they implemented during the 2020-21 offseason. Rather than using the Yankees' considerable financial might to shop at the top of the market for multiple, difference-making free agents - Steinbrenner appears to be content to let Cashman look for reasonable and team friendly deals. Not all offseasons are the same of course, but the Yankees approach this offseason seems like it is very similar to the way the team operated in 2020-21. There’s a good chance that when we look back on this offseason, Cashman will have made at least one big, but reasonably priced, signing (think: Cody Bellinger perhaps) while also being resourceful in making a trade or two. He’ll also no doubt spend the bulk of his time adding depth - most of which won’t wind up mattering.

Looking back to the 2020-2021 offseason, LeMachine (as he was called), was a great presence in the clubhouse and at the time. His contact oriented approach at the plate and his stellar glove work combined with his positional diversity to convince Cashman that giving the then 32-year old a six-year contract with an AAV of $15 million was a sound move. In retrospect, the move backfired four and a half years into the deal and the Yankees wound up designating LeMahieu for assignment. Is it wise to extend what will likely be an even longer contract with a much higher AAV to the soon to be 31-year old Bellinger?

Some of Bellinger’s underlying metrics give me some cause for concern, as I think there is a good chance that his performance will decline sharply over the course of a long term deal - starting as soon as this coming season.  Hopefully normal baseball fans will forgive me for leading with this, but this past season, Bellinger’s XWOBACON is concerning. I’m not referring to a new type of bacon here, but rather - it's one of those wonderful, hypothetical stats created by StatCast, that attempts to isolate the contact part of a player’s game (excluding walks and HBP’s) by assigning run values to batted balls - ultimately showing if a player is lucky or unlucky.  Bellinger’s xWOBACON was .337 – which is a very good number by the way, but what on earth does it mean? Simply put, the contact Bellinger made last season resulted in significantly lucky outcomes, so he had a better than expected season.

Last season and by contrast, this off-season’s top free agent - Kyle Tucker (who is one year younger than Bellinger) posted a .384 XWOBACON (significantly better than Bellinger’s .337) which reveals that while many of the outcomes of his contact were very unlucky last season, he still outperformed Bellinger by a wide margin.

Additionally and more concerning, currently available public projection services like Steamers and FGDC are calling for Bellinger’s 2026 performance to drop from last season’s .347 wOBA to a .336 and likewise, they’re calling for his wRC+ to dip from 125 down to a 116. The same services suggest Tucker’s 2026 performance, projected to be .363 wOBA/136 wRC+ will not only be superior to that of Bellinger’s, but Tucker’s performance will remain steady in 2026.  In short, teams with the financial ability to sign Tucker can be confident that the player they’re inking to a long term deal will likely perform well in 2026 and likely, beyond. Whereas, Bellinger is likely to regress, starting in 2026, which makes one wonder - will a six or seven-year deal wind up similarly to the deal Cashman gave to DJ LeMahieu during the 2020-21 offseason?

Given the Yankees pursuit of Bellinger, who is projected to be awarded a contract for far less than the one Tucker will likely earn, watching this offseason unfold is a lot like watching the 2020-2021 offseason. Remembering back to then, Cashman had enough money in the budget to also bring Brett Gardner back on a one-year ($9 million) deal for outfield depth. When it came to addressing the Yankees starting rotation, Cashman was inclined to roll dice on a low-cost, high-risk/high-reward signing of Corey Kluber - who signed for $11 Million. Then, Cashman continued to gamble, as he traded with the Pirates for  Jameson Taillon -  who came with one-year of control for $2.2 million. Taillon had the makings of being a good fit as he was a former teammate and good friend of Gerrit Cole.

Selling low on Taillon, due to his multiple injury/health related red flags, the Pirates received back from the Yankees a very healthy Triple-A starter - Roasny Contreras with years of team control remaining while also hauling in a tranche of prospects in the deal. Taillon wound up being worth 3.7 in bWAR during his time with the Yankees whereas Contreras was only worth 1.4 bWAR with the Pirates, so thus far, Cashman appears to have won the trade by a mile - considering none of the other players he traded have yet made it to the Big Leagues. In a few more years, we’ll have a definitive verdict on this.

Cashman gambled on the oft-injured Kluber and the results he delivered ultimately weren’t impactful enough. At the time the Yankees signed him, he was coming off a broken unla (forearm bone that acts as a stabilizer and is key for movements like bending the arm and rotating the hand) in 2019, but Kluber pitched pretty well for the Yankees for a month and a half, even no-hitting the Rangers on May 19th of 2o21, but soon after regaining his old form and looking like a true ace again, he developed shoulder problems and went on the disabled list from the end of May through the end of August that season.

Like the Kluber signing, trading for Taillon was a calculated gamble on Cashman’s part, as he was coming off his second Tommy John surgery at the time and he also had some other significant health concerns as well.

Given that Steinbrenner permitted Cashman to sign LeMahieu to a reasonably yet significant contract during the 2021-22 offseason, it's hard to place the blame on Cashman for finding two very creative and even more cost effective solutions to slot into the Yankees rotation behind Gerrit Cole - whom the Yankees had spent big money on (9 years and $324 million) the previous offseason. Will Cashman wind up having to be creative again, when it comes to adding pitching? If signing a starter isn’t in the cards, one thing is certain: Cashman will desperately try to make a trade and it may wind up looking eerily similar to the one he made for Jameson Taillon.

During the 2020-21 offseason, Cashman was forced to gamble and be creative due to Steinbrenner’s unwillingness to spend big. Adding Kluber and Taillon for the combined bargain-barn price of $13.2 million was clearly more palatable to Steinbrenner than authorizing Cashman to add any of the top starters that were available during the 2020-21 offseason. It should be noted, the top available starter that offseason was none other than Trevor Bauer, who wound up receiving a 3-year $102 million contract from the Dodgers.  Besides being a sworn enemy of Gerrit Cole, Bauer clearly had attitude related red flags and the Yankees wisely passed on involving themselves with him as he clearly wasn’t a good fit with the Yankees.

Other notable free agent pitchers during the 2020-21 offseason were Marcus Stroman, Masario Tanaka and several other names, none of which were viewed as needle movers at the time. Sometimes the market is flush with difference makers and sometimes it isn’t.

This offseason, there appear to be many difference makers on both sides of the ball and Cashman has even acknowledged as much. The problem this offseason though is that it’s been tough sledding to date - there hasn’t been any snow for Santa’s sleigh to glide on in order to deliver Yankees fans with a fine present or two.

Cashman’s hands appear to have been tied behind his back to this point in the offseason, but he’s actually indicated that none of the “inventory” that he’s interested in has come off the board yet. This means that he’s patiently waiting to see if the markets for certain player(s) the Yankees want most come down. Hal Steinbrenner certainly prefers reasonable or team friendly deals over having to spend top dollar.

If Bellinger’s market becomes too expensive, where will Cashman turn in order to fill in the roster? The Yankees need a difference making, right-handed bat capable of playing corner infield and or outfield - it has to be someone who crushes left-handed pitching.  This isn’t the first time I’ve floated the name, Miguel Andujar, here on SSTN but now I’m doing so in an actual article, as I have a feeling that an out of the blue reunion between Miggy and the Yankees is becoming more and more likely as the offseason trudges along.

Andujar, who is projected to land a one to two-year deal with an AAV around $5.5 million - which Steinbrenner would find to be much more appealing than paying Tucker or Bellinger five or six times that! A move like signing Andujar would be kind of like when during the 2020-21 offseason, the Yankees brought back Brett Gardner.

Miggy had a strong year with the Reds and several teams are interested in his contact skills as an outfielder/DH. While Miggy would provide some insurance in case Giancarlo Stanton goes on the DL with yet another injury, he’d also be a serviceable, though below average, platoon option to pair with Jasson Dominguez in left field, due to his ability to mash left-handed pitching (171 wRC+/.987 OPS ly vs LHP). Another nice thing about Andujar is that he posted very playable 108 wRC+/.760 OPS numbers against right-handed pitching.

This offseason, it appears that Cashman would like to give manager Aaron Boone some options against left-handed pitching. Andujar is a good fit in this regard. Andujar would also pair well in the lineup with recently signed Amed Rosario, who is another example of Cashman bringing in an inexpensively priced player who hits left-handed pitching very well and who can play all over the infield. Like Jasson Dominguez, where Andujar is deficient as an outfielder is that he lacks range.

That said, Miggy is hands down a better left fielder at this stage than Dominguez is and considering that Dominguez can’t hit left-handed pitching, if the Yankees keep him in their plans for 2026, they’ll likely need a platoon candidate for him - which is why Miggy makes sense but that’s probably selling Miggy a little bit short because if the Yankees did sign him, they really wouldn’t need to keep Dominguez around at all so they would probably want to trade him.

Should the Yankees fail to land Bellinger, another player they’ve actually been linked to is Austin Hayes, though his bat lags behind Andujar’s, Hayes is a better defender in left field (even though both players have cannons for throwing arms) and overall he grades out as being average to a tick above average. On a team like the Yankees, Hayes would be a platoon option and he’d likely sit when Dominguez plays against right-handed pitching. The Reds gave Hayes 289 at-bats against right-handed pitching last season and he produced 88 wRC+/.708 OPS results. Dominguez meanwhile put up 116 wRC+/.768 OPS so the platoon match is very much a fit for these two players.

Signing Andujar and trading Dominguez is a better way for the Yankees to move the needle though, that much remains very certain. Hayes is also projected to sign for one-year at between eight and ten million, so he’s more expensive than Andujar would be, likely because he’s a better defender. Either move, signing Andujar or Hayes, would be very similar to the Yankees bringing back Brett Gardner during the 2020-2021 offseason.

Would a 2025-26 offseason comprised bringing back Trent Grisham,  then signing one of Bellinger or a front line starter and perhaps adding Miguel Andujar, while also adding some lesser pieces like Rosario, Cade Winquest and Ryan Yarbrough feel very similar to how Hal Steinbrenner’s Yankees handled the 2020-21 offseason? All signs seem to point to a similar strategy and way of thinking.

If the strategy didn’t work in 2020-21, what makes Steinbrenner think it will work this time? That’s kind of a rhetorical question I’m asking, because the answer clearly is - “It won’t work this time either.” Will it? It just doesn’t feel like the Yankees are going to do enough to move the needle. Advantage Blue Jays, Red Sox and possibly even the Orioles! The Yankees championship window is closing folks, right here, right now, before our very eyes.

With as much money as Steinbrenner has tied up in the Coles, the Judges, Stantons, Frieds and Rodon’s of the world, it’s hard to fathom why Steinbrenner refuses to change his thinking a bit. I hope that we all wake up tomorrow or one day soon to some news that makes this article a distant memory about the rantings of Cary Greene, but I’m sticking my sword of words in the sand for all to read. Is Hal Steinbrenner for real? Do I have to watch Cashman reenact the 2020-2021 offseason all over again? Are the Yankees still refusing to spend like the big, hairy, pinstriped gorilla they are?

Many of the offseason plans different writers, including myself, made in November are at this point laughably off base. We all knew they would be too, but we laid our plans anyways, because to not state what you hope your favorite team will do during the offseason is almost sacrilegious - it means you’re not really a true Yankees fan in my book. True fans have to at least imagine or hope for things to get excited about. Early on in the offseason, most of us busied about as we commented on this article and that article, passing the time with our wishful thinking. It made for good fun, but wow, Steinbrenner is really taking the air out of the pinstriped balloon this offseason, isn’t he?

Personally, I doubted the Yankees would extend the QO to Trent Grisham, but I’m on record for being staunchly in support of them doing so. I realize this places me in the minority here on SSTN, but I contend that what Grisham did in 2025 is not only real, but repeatable. There’s plenty of StatCast data that says it’s very possible that Grisham will have another good year in 2026. Also, I feared Bellinger’s market might outprice him and I knew that Cashman needed a little leverage when dealing with super agent Scott Boras, regarding hammering out a contract to bring Cody Bellinger back to the Yankees.

Another thing I wanted Cashman to do was to put a full court press on signing either the left-handed, durable, ground ball machine Framber Valdez or perhaps to make an all-out run at Tatsuya Imai as a fallback. I also wanted some coin spent on the bullpen - in the forms of Phil Maton and Robert Suarez - both of whom are off the board at this stage.

There was no chance that Steinbrenner would spend a combined $64 million in AAV to address the Yankees rotation and revamp the bullpen. Zero. None! I knew it too, but I wished for it to happen anyway. Thus far, Cashman has spent only paltry sums of money on pitching and he’s fallen dramatically short of what I hoped to see him do. It’s my belief that if he continues with this strategy, it will doom the Yankees chances at winning a World Series in 2026. With as many massive question marks as the Yankees have in their rotation, not upgrading it this offseason is a recipe for disaster.

Not to mention, the bullpen has only become worse this offseason and I’m afraid that’s not going to cut it either. I’m handing out low midterm marks this offseason for Steinbrenner and Cashman regarding their lack of action in the pitching department.

Early this offseason, even if the Yankees wound up adding a difference-making starter, it was my belief that the Yankees lineup needed to improve from last season. Bringing back Cody Bellinger doesn’t move the needle, especially when considering that Paul Goldschmidt, who started the season very hot, is also not likely to be returning. I knew that Bellinger was a great fit for the Yankees last season, both on and off the field and he remains so - even if he is likely going to regress.

Is Cody Bellinger going to be worth the contract he receives? That depends on how many front offices decide that his fairly lucky season last year is something he’ll sustain or even build on. His agent, Scott Boras, also knows Bellinger is a good fit with the Yankees. He’s also reporting that Bellinger’s market is very robust and he’s doing this for a reason: He’s trying to extract maximum value for Bellinger. Have the Yankees often been used for negotiating leverage by Boras?

When the season ended and baseball minds started shifting towards offseason thoughts, many felt that bringing Bellinger back on a team friendly deal was probably not in the cards and we’re seeing the struggle over this play out presently as projections regarding the contract Bellinger will receive have now soared into the $30 million range in AAV over the course of a multi-year deal.

While 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, I reasoned that bringing him back would likely not be in the cards as the juice wouldn’t be worth the squeeze on a long term deal. If the Yankees do sign Bellinger, he gives them an insurance plan in center field for sure, but does he represent a long term solution? I doubt that very much, so - no 2026 Yankees offseason plan would be complete without providing a long term solution in center field. Somebody has to patrol the expanse that Joe Dimaggio and Mickey Mantle used to roam for the Yankees. Grisham is set to run it back again this season with the Yankees and presuming he’s healthy, he should be much better defensively than he was last season, during which he played with a nagging hamstring issue for several months - which limited his range. But what about insurance at the position and also, what’s the plan for 2027 and beyond?

Bellinger represents center field insurance in the short term, but I wonder, will Jasson Dominguez or Spencer Jones be the next in a long line of storied Yankees centerfielders? It remains to be seen, but personally I’m much more bullish on Jones than most here on SSTN are and I want you all to remember that! Hold me to it if he winds up not panning out. Personally, I think he’ll figure it out and when the 2027 season opens, Jones will be the starting center fielder. Therefore, my offseason plan didn’t center on bringing back Cody Bellinger as I think there are better ways to spend $30-plus million in AAV. He’s not the guy I have been hoping to see signed.

This offseason, I’ve written that I’d like the Yankees to make a run at signing Bo Bichette. Not only could Bichette move to second base in the future or as needed, but there’s a likelihood that, if healthy, he could return to playing tolerable defense at shortstop. While Bichette had a down year last season defensively, even by his below average standards, if he’s healthy there is no reason to suspect he wouldn't rebound into the form of a playable shortstop. 

Defensively, Bichette 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 or eight-year deal in the $200-plus million range. If the Yankees were to sign Bichette,  it would be a very interesting strategy, he’ll command about $30+ million in AAV so if the Yankees pivot away from Bellinger - and I hope they do - signing 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, while also possibly adding someone like Andujar or a Hayes. As risky and experimental as it sounds, it's a gamble that has a lower floor but a very high ceiling. It’s also a gamble that leaves the Yankees very thin in center field, so if Grisham gets injured and is out for significant time, the Yankees would have to either use Dominguez there, or promote Jones, or worse yet - move Judge back to middle outfield.

Age is also on Bichette’s side, so if we’re going to brandish the idea of a long-term deal with a high AAV, the 27 years-old Bichette is a full five-years younger than Bellinger, so Bichette should be an even more attractive to Brian Cashman Bellinger is.

Are we going to get a repeat of the 2020-21 offseason, which would see the Yankees bring back Bellinger and shop primarily in the bargain isle to fill the roster out, or will the Yankees actually move the needle by acquiring a clear rotation upgrade while also adding even more offense that what Bellinger is projected to deliver? I’m betting that we’re looking at a 2020-21 offseason repeat, while at the same time, I’m foolishly holding out hope that we’ll see more than just an old, stale, poorly constructed plan repeat itself yet again. Thoughts?