The New York Yankees eked out a 2-1 series victory over the Boston Red Sox in the AL Wild Card, only to fall flat on their faces in a blowout series loss to the Toronto Blue Jays. It was a sobering reminder that life without Juan Soto won’t be so easy. New York went above and beyond all reasonable expectations to compensate for Soto’s departure, but at the end of the day, Brian Cashman’s roster featured too many holes.

Another consequential offseason awaits. Cody Bellinger, Devin Williams and Trent Grisham highlight a long list of important free agents. The Yankees will hope to get Gerrit Cole close to a return from Tommy John surgery, but for all the talent on this roster — including MVP candidate Aaron Judge, Cy Young candidate Max Fried, and annual 30-30 threat Jazz Chisholm — there’s something missing.

Perhaps it starts with a new manager. A lot of Yankees fans are tired of Aaron Boone, although I’d caution against expecting change there. New York’s bullpen was heavy on big names and light on impactful pitching down the stretch. The defense is a total mess. The offense, while loaded with slug, can dip into frustrating cold spells. New York needs to button up the seams of its roster and try its best to mitigate the weaknesses around a World Series-caliber core.

We can expect the Yankees to operate aggressively in free agency, but another avenue to dramatic change is the trade market. New York has the financial capital and prospects necessary to pull off a huge swing there. Here’s where Cashman should aim.

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RHP Emmanuel Clase, Cleveland Guardians

Emmanuel Clase spent the majority of the 2025 season on ice amid an MLB gambling investigation. He faces severe penalties (and the potential end of his career) if the league finds evidence of wrongdoing, so the Yankees will need to make sure Clase is in the clear before pushing the chips in. But, if Clase clears the necessary hurdles for a 2026 return, there’s a decent chance the Cleveland Guardians put him on the market. New York should pounce.

Clase is under club control at an affordable rate through 2028, so the Yankees would inherit a shutdown closer with four more years of top-shelf production on the horizon. New York’s bullpen remains a huge point of emphasis this offseason, even after a frenzied barrage of trade deadline additions. Devin Williams is a free agent. David Bednar is a sturdy closer in his own right, but he’d look a heck of a lot better as the setup man for Clase, who gets a ton of chases and soft contact with his upper-90s cutter and a slider that sweeps through the zone like something straight out of Fruit Ninja.

In return, Cleveland receives No. 5 Yankees prospect Bryce Cunningham, a 22-year-old righty with a devastating three-pitch combo. His changeup has the shape of a true A-plus pitch, and he locates the fastball and slider well enough to envision Cunningham as a major piece of the Guardians rotation down the line. T.J. Rumfield, New York’s No. 25 prospect, can handle extra first base reps, a position of need for Cleveland. He hits well for average. Brendan Jones, New York’s No. 12 prospect, is a speedy, smart outfielder who feels like the epitome of Guards Ball and would fit like a glove in Steven Kwan’s place, should Cleveland trade its All-Star left fielder.

LHP Mackenzie Gore, Washington Nationals

Mackenzie Gore’s name popped up in trade rumors around the deadline and there’s a chance the Washington Nationals revisit those conversations in the offseason. There’s no immediate pressure to deal Gore, who’s under club control through 2027, but we know the drill. Washington almost certainly won’t pay Gore’s market price once free agency comes around. An extension is unlikely at best. The sooner he’s dealt, the more they get in return.

This past season was a challenge for the 26-year-old lefty, who finished with a 4.17 ERA and 1.35 WHIP in 30 starts. But he also made his first All-Star appearance, notching an impressive 185 K’s in 159.2 innings. Gore offers four solid pitches, specializing in a zippy mid-90s fastball and a droppy low-80s curve that can keep hitters guessing. When he’s locked in, Gore looks like an ace in the making. Few teams develop pitchers better than New York, and the Yankees have the necessary capital to extend or re-sign Gore when the time comes.

In exchange, the Nationals add a couple pitching prospects to their farm system in righties Elmer Rodriguez-Cruz (No. 3 prospect) and Ben Hess (No. 6 prospect), both of whom should be vying for MLB innings within the next couple years. Rodriguez-Cruz is a tall, spindly pitcher with a deceptive release off great extension. Hess struggles with command, like most young pitchers, but his fastball flies off the hand and his curveball is gnarly when he locates it. Dillon Lewis (No. 16 prospect), an outfielder with plus baserunning and excellent pop off the bat, could factor into a talented outfield group that already features James Wood and Dylan Crews.

1B Yandy Diaz, Tampa Bay Rays

The Yankees have an opening at first base as Paul Goldschmidt hits free agency. I’m generally a proponent of starting Ben Rice there full-time, but New York has been hesitant to embrace Rice as an everyday first baseman. One solution? Trading Austin Wells, which opens the door for Rice to spend the majority of his reps at catcher. That then opens the door for a Yandy Díaz trade.

Odds are the Tampa Bay Rays don’t want to send Díaz to a division rival, but value is value and Díaz is 34, entering the final year of his contract. It’s a pure rental for the Yankees, albeit an impactful one. This past season was one of Díaz’s best yet. He hit .300 with an .848 OPS and a career-high 25 home runs. For a team in need of consistency beyond Judge, Díaz brings valuable experience and a highly disciplined plate approach.

There is downside, of course. He’s an older rental and Díaz is also a weak link defensively. Ideally the Yankees could plug him in at DH, but putting Giancarlo Stanton in a no-go at this point. Between Díaz at first and Rice behind home plate, the Yankees would suffer on defense. That’s a complicating proposition for a team alreay rife with defensive concerns. New York would need to shore up other positions to really optimize this trade.

For Tampa, Austin Wells gives them a solid long-term solution behind home plate. He took a step back in 2025 compared to his rookie season, but the Rays (like most teams) would happily take 20-plus home runs and 60-plus RBI from the catcher position, with hopes that Wells can cut down on strikeouts and rebound defensively. Dillon Lewis gives Tampa a talented outfield prospect to bring up at a position of need.

OF Byron Buxton, Minnesota Twins

The Minnesota Twins basically cleaned house at the trade deadline. One of the few major pieces to survive that fire sale was All-Star outfielder Byron Buxton, who is under control for a hair over $15 million annually through 2028. That is incredible value for sucha dynamic, well-rounded player, but the Twins are in a financial crunch and Minnesota has no plans to contend in the immediate future. That could mean Buxton’s name pops up in rumors again, and perhaps he’s more willing to waive his no-trade clause than he was a few months ago.

The Yankees will need to factor in the development of Jasson Domínguez and other top prospects when trading for an outfielder, not to mention the potential re-signing of Cody Bellinger or Trent Grisham. Conventional wisdom suggests that Grisham is gone. Bellinger is a more complicated case. That said, Bellinger can always slide to first base, especially if Ben Rice is moved to catcher on a more regular basis. If neither re-signs, then it shouldn’t be hard to fit Buxton in centerfield, Judge in right, and Domínguez in left. Buxton’s defense alone would elevate New York’s standing in the AL East, but his offense is the real source of electricity.

Buxton checks just about every box. He hit .264 with an .878 OPS and 35 home runs this past season, adding 24 stolen bases while supplying excellent defense in centerfield. At 31 years old, he’s not a spring chicken, but Buton should have a few more prime years left in the tank, at the very least. He’s an excellent candidate to bat leadoff in front of Judge. If Bellinger leaves, he’s an upgrade. If Bellinger returns, New York has the deepest outfield depth chart in MLB, so the point where Bellinger might shift to the infield.

Minnesota is well-compensated, of course, as Buxton is a controllable superstar on a bargain contract. Spencer Jones (No. 4 prospect) needs to keep his strikeouts in check, but the tall lefty is one of the best power bats in the Minors. Cunningham can supplement a young Twins rotation sooner than later, while Dax Kilby (No. 7 prospect) gives them an extremely disciplined hitter and a quality defender at a premium position.

LHP Tarik Skubal, Detroit Tigers

The Yankees would need to empty the entire clip for Tarik Skubal, even on an expiring contract, but c’mon. New York would have a chance to go into October with Skubal, Gerrit Cole and Max Fried headlining the rotation. That is an impossible gauntlet for most opponents, especially if Cole can return to pre-injury form.

It will be hard for the Detroit Tigers to part with Skubal, but he’s not going to sign a discount extension and losing him for nothing is not an appealing outcome, especially since the Tigers are ill-equipped to meaningfully improve their offense this winter. Detroit flirted with signing Alex Bregman and other big-ticket free agents last offseason, but until it actually happens, this is a quality regular season team with fatal postseason flaws.

Skubal has the necessary leverage to force Detroit’s hand if he wants to (not that he would). The Yankees stand out as not only an ideal landing spot if he wants to contend, but as a team with the financial wherewithal to re-sign Skubal as a free agent, should they choose to. That can help Cashman justify the flood of outgoing assets. You need to give something to get something, and Skubal is the best pitcher in MLB right now.

Detroit supplements its offense with two sluggers nearing their MLB call-ups: Jones, a towering lefty slugger in the outfield, and George Lombard Jr., a five-tool middle infielder and the son of ex-MLB player and Tigers bench coach George Lombard Sr. It feels right! Plus, Detroit adds two future rotation cogs — hard-throwing righty Bryce Cunningham and 6-foot-7 lefty Henry Lalane, with a disappearing changeup— to develop in their pitching incubator.