What Should the Yankees Offseason Look Like? Part 1 of 2:

What Should the Yankees Offseason Look Like?

Part 1 of 2:the Rotation and the Bullpen

By Cary Greene

October 31, 2025

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Now that the Yankees have been eliminated from the playoffs once again, it’s time to start thinking about what offseason moves the Yankees should make. Of course the biggest problem facing the Yankees is what to do about Trent Grisham and Cody Bellinger. Fans are wondering if the Yankees will try to sign either or both of them.

After The way Max Fried pitched in September, he made an emphatic statement that he was the unquestioned ace of this year’s Yankees team as they headed into the playoffs. He pitched superbly against Boston in Game 1 and if Boone hadn't taken him out prematurely, the game might have turned out differently. Removing Fried with one out and no one on in the sixth-inning, simply because he was at 102 pitches, was a questionable move, considering who Boone turned to in a tight and crucially important game. Luke Weaver blew the game and the Yankees were forced to play a three game series against the Red Sox.

I’m not debating that Fried shouldn’t have been removed after throwing 102 pitches, but playoff baseball calls for all hands on deck and we all know Fried could have finished the inning. Heck, he threw 107 pitches in his final start of the season. Winning in the postseason means adopting a leave everything on the field approach and Aaron Boone lacks that kind of attitude. The Yankees are very lucky that they even got the opportunity to advance past Boston at all. If it wasn’t for Cam Shlitler’s 8-inning, Game 3 gem, New York could well have come up short and if that had happened, the decision to remove Fried would be one Yankees fans would be talking about for a very long time.

Hopefully, Brian Cashman will one day assemble a championship level pitching staff. Last year’s team posted a regular season 105 ERA+ and that’s far below the 114 ERA+ average that past championship teams have averaged. Injuries once again derailed the Yankees starting rotation and make no mistake, losing Gerrit Cole was a colossal blow to the Yankees season.

Regarding Cole, who knows what to expect in 2026? He's a winner, for sure and he's tough too, so I’m hopeful that he can make his way back and be a front of the rotation piece for the Yankees this coming season, but TJS can affect different pitchers in different ways. I’m choosing to notice Nathan Eovaldi - a power pitcher similar to Cole - he's had not one, but two TJS and he's better than ever these days. This gives me hope that Cole might indeed return and gradually become lights out once more. Hopefully, his arm has a lot of innings left in it!

In order to build a championship team, Brian Cashman needs to put even more focus on his starting rotation. There's no question that injecting an ace like Cole back into the mix next season would be a huge boost to the Yankees rotation, but considering Carlos Rodon won’t be ready to start the season, Cashman will need to improve the Yankees starting pitching as his absolute top priority this offseason. Clarke Schmidt will also be sidelined for a large chunk of the 2026 season and this further punctuates the Yankees need for starting pitching.

Given that Cole, Rodon and Schmidt will all not be ready to contribute at the start of next season, the Yankees plans for a return to the World Series will very much hinge on the pitching staff Brian Cashman builds this offseason and in light of this, I must ask the million dollar question at this juncture in today’s article:

Assessing the Yankees Rotation and More

Which starting pitchers should be on Cashman and the Yankee’s radar this offseason and of equal importance, who should the swing-men who could either spot start or step into the rotation if needed, be in the bullpen? Answering this question is where I believe the Yankees 2026 roster building plan should start. There are free agents to consider, there is some home grown talent knocking on the door to contemplate and of course, there are potential trade targets for Brian Cashman to look towards as well.

During this season’s stretch run, Cam Schlitler burst onto the scene and seems to have embedded himself into a Yankees rotation headed once again by Max Fried. Schlitler embraced the Yankees strength and conditioning plan and much of his success is attributed to his willingness to work hard and his incredibly positive attitude. He’s also a cerebral type of pitcher who has a great feel for pitching. Aside from Fried and Schlitler, the Yankees will need to improve their rotation, while also creating a certain level of flexibility in their roster as they will need room when Rodon, Cole and possibly Schmidt return at various junctures.

Next, there’s the case of Luis Gil, who lost 1.3 mph on his four-seamer last season and was knocked out of Game 1 of the American League Division Series by the Blue Jays. Gil is presently, on paper anyway, the Yankees number three starter and this shouldn’t make Cashman and the Yankees braintrust feel very confident. Gil’s statcast page from last season isn’t very encouraging and rumblings are already out there that suggest moving Gil to the bullpen might be the play.

Should the Yankees move Gil to the bullpen, since he is markedly more effective in high-leverage situations, where his live arm and above average fastball plays up? Given the Yankees lack of established rotational depth, it may behoove the Yankees to hold off on making that decision, at least to start the season. Assuming the Yankees agree with my assessment, they’ll need at least two more starters to begin the season.

Not mentioning Will Warren yet has been purposeful. His lack of ability to execute his secondary pitches illustrates his continued need for development. While he did eat 162.1 innings for the Yankees this season, the only reason the Yankees stuck with him so long was due to a litany of reasons. First and foremost, Marcus Stroman and Carlos Carrasco were both pretty bad for the Yankees. Compared to Warren, they were both downgrades and so the Yankees cast them off. Ryan Yarbrough’s untimely oblique injury also magnified the need for Warren to make additional starts and lastly, the ineffectiveness of Alan Winans, who failed to capitalize during his three game stint when he was promoted in late June last season also afforded Warren even more innings.

Had anyone told me at the start of last season that Will Warren was going to pitch 160+ innings for the Yankees, I would have been hopeful that the reason would be that he flashed unbelievable stuff and perhaps he would force his way onto the scene. This wasn’t the case. Warren’s StatCast page tells a very different story and once viewed, it becomes clear that Warren pitched way too many innings for a team that badly lacked pitching depth. Fortunately, Cam Schlitler worked his tail off and he finally stepped into the back end of the Yankees rotation down the stretch and the rest is recent history.

Most Ready Prospects of Significance

There are a few Minor League starters that the Yankees should feel pretty decent about. Elmer Rodriguez-Cruz will start the season in Scranton and he might be in line for a call up to the Show at some point. Winans also probably deserves another look at some point, though he did get violated during his three-game cameo, it was a very small sample size and his numbers in Scranton jump right off the stat sheet.

Beyond Cruz and Winans, somehow Cashman didn’t trade Carlos Lagrange, Brendan Beck or Ben Hess away at last year’s Trade Deadline and all three seem to be potential candidates to impact the Yankees at some point next season. Because the Yankees also need to revamp their bullpen and also address positional areas of need, Cashman will have to work his magic this offseason. He’ll have to first get the starting rotation shaped up though, so naturally, the Yankees will need to look towards free agency and potentially even consider a trade or two as a means of positioning their rotation.

Best Fit Free Agent Starter

On the free agency front, the biggest needle mover is Framber Valdez, who is a great fit for the Yankees. Not only has he demonstrated that he can pitch deep into games, but he would bring a plus-fastball and more left-handedness to the Yankees rotation. He won’t come cheap, but signing him would be an excellent offseason move for Brian Cashman and the Yankees.

High-end projections, reported by Yahoo Sports, approximate Valdez commanding $204 million over six years, which would place him among the highest-paid free agents in this year’s class. He’ll likely get a Max Fried level deal this offseason.

Looking towards the trade market, the Brewers could decide to throw their nets out and troll for a massive haul in return for their ace, Freddy Peralta. I’m not sure if the Yankees match up to what the Brewers would want in return, should they decide to dangle Peralta. One thing is certain though, there will be many suitors if this happens. Due to the Yankees need for outfielders and a shortstop, I’m not sure the Yankees would deem it wise to mortgage their future for one season of Peralta.

Other outlandish Yankees trade rumors are circulating regarding the usual top shelvers like Paul Skenes and Tarik Skubal and though I’m also a Pirates fan, I think Skubal would electrify Yankee stadium even more than Skenes would, if the Tigers were ever to trade him to the Bronx Bombers. I’m trying to keep this article realistic though, so outside of a huge trade for Peralta, Skenes or Skubal, the play seems to be to pony up to the bargaining table and sign Valdez to provide stability for the Yankees in 2026.

If Valdez were signed, the Yankees could open the season with Fried, Valdez, Schlitler, Gil as their top four starters. They could solve the fifth starter conundrum with any number of other very inexpensive options - such as bringing back Ryan Yarborough or using a combination of openers from the bullpen, while sprinkling in Winans, Warren and whomever else, until such time as Rodon comes back.

Once Cole returns, Gil could shift into the bullpen and the Yankees rotation would be Fried/Cole/Valdez/Rodon/Schlitler and that my friends, THAT is a rotation that Yankees fans can believe in, so mark me down as being whole heartedly in favor of prioritizing Valdez above all other free agents this offseason.

Bullpen Upgrades

Regarding the bullpen - it's going to be imperative for Cashman to bring in a few lock down set up men. I clamored for years for Cashman to go get Bednar and at this year’s Deadline, I got my wish. Bendar proved to be an ideal closer for the Yankees and his pitbull mentality played well down the stretch. With Bednar locked in as the team’s 2026 closer, Cashman should focus on relievers capable of holding leads.

Somehow, the Yankees bullpen ranked eighth in holds last season (with 100 total) and I thought that was a very surprising stat given how bad the bullpen seemed. A hold is credited to a reliever who successfully preserves a lead in a high-leverage situation, but who is not the closer finishing the game. To qualify for a hold, the relief pitcher must enter the game with a lead of no more than three runs, or with the tying run on base, at bat or on deck. They must also record at least one out and leave the game without having relinquished the lead.

There was a significant gap though between the Yankees and the Dodgers, whose bullpen ranked first in this category with 125 holds. It stands to reason, great teams hold leads once they get them. Good bridge relievers shorten games, so in lock step with this notion, I believe priority number one regarding the Yankees bullpen is to acquire a lock down bridge reliever - someone the Yankees could bring into the game in the sixth or seventh inning, who they could count on to flummox opposing batters with very different looking stuff than perhaps the starting pitcher had.

After racking my brain, I think one of the first kind of under the radar moves Cashman should make this offseason involves targeting Phil Maton - he's an obvious fit in my estimation. He's a guy who can rack up holds (he had 22 last season)  and hand leads over to the back end of the bullpen and his combination of offspeed pitches would provide a vastly different look than many of the Yankees power starters would give opponents, likely flummoxing them nicely. Adding Maton closes the gap on the Dodgers bullpen almost single handedly - although we would have to deduct (and replace) Luke Weaver’s 21 holds and Devin Williams’s 15).

Perhaps the Yankees are still struggling to fill the niche that Garrett Whitlock, who Cashman lost back in the 2020 Rule 5 Draft, has plugged for the Red Sox. While Whitlock is long gone, he did register 24 holds last season for Boston. If Maton were plugged into the role of a bridge reliever, he’d go a long way towards upgrading the Yankees bullpen.

More than likely, the Yankees will part ways with one or both of Luke Weaver and Devin Williams this offseason. Personally, I’d be perfectly okay with the Yankees ditching both, as it would give Cashman a chance to upgrade. It’s no secret that the Yankees bullpen needs a right handed fireballer and a lights out lefty.

Robert Suarez, who had 40 saves last season with the Padres, should be Cashman’s next bullpen target. He’d be a big upgrade from Devin Williams, but he’ll be very expensive for a 35-year-old reliever. I’m not sure if it’s realistic to expect the Yankees to sign pricy relievers given all of their other team needs. 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.

Maybe Suarez’s market will simply become too rich for Steinbrenner and the Yankees, in which case another right-handed, high leverage reliever for Cashman to target is Raisel Iglesias, who had 34 saves last year with the Braves. While Suarez is a better fit for what the Yankees pen lacks most  (considering his blazing fastball), Iglesias has become a battle tested, durable, high leverage reliever. Would Iglesias be an upgrade over Williams or Weaver? It's hard to say for sure, because pitching well in New York isn’t something everyone can do.

One of the top available left-handed relievers on the market this offseason is Caleb Ferguson, who the Pirates dealt to the Mariners at the Deadline this past season. If Cashman was able to land Maton, Suarez and Ferguson, the bullpen could be considered upgraded. I’m proposing that the Yankees focus mostly on pitching this offseason and I believe that if they do that, the rest will take care of itself.