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The Yankees‘ offseason, so far, has been uneventful.

Aside from some minor signings, and one big qualifying offer being accepted, New York has yet to fill out its roster to try to get back to the World Series. While division rivals like the Red Sox and Blue Jays have already made big splashes, Yankees GM Brian Cashmanis seemingly biding his time. While the team’s needs and priorities are very obvious, the Yankees enter the MLB Winter Meetings with a lot of questions and even more work to do.

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Here’s a checklist of what the Yankees need to do this week during the Winter Meetings in Orlando…

Bring Cody Bellinger back

The biggest offseason move the Yankees need to make is to re-sign Bellinger. Cashman got a steal when he made the trade with the Cubs last offseason to bring the former NL MVP to The Bronx. Bellinger had one of his best seasons as a pro and helped the Yankees lengthen the lineup and shore up the defense in the outfield. He won games single-handedly with his defense alone this past season and has proven that he’s perfect for the pinstripes.

It’s clear Bellinger is Cashman’s priority this offseason, just as Juan Soto was a year ago. And while that pursuit didn’t pan out, Cashman can’t possibly allow Bellinger not to return, especially when teams like the Dodgers and Mets are vying for his services.

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It won’t be easy, Bellinger — who is represented by Scott Boras — will look to have a lucrative multi-year deal and the Yankees may have to go further than they otherwise might be comfortable with; that’s how important Bellinger is to the 2026 Yankees. Aaron Judgeand Trent Grisham can’t be the only veterans in the outfield next season while they try to capture lightning in a bottle with Jasson Dominguezor Spencer Jones.

Oct 2, 2025; Bronx, New York, USA; New York Yankees outfielder Cody Bellinger (35) runs to home plate in the fourth inning against the Boston Red Sox during game three of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium.

Oct 2, 2025; Bronx, New York, USA; New York Yankees outfielder Cody Bellinger (35) runs to home plate in the fourth inning against the Boston Red Sox during game three of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. / Vincent Carchietta-Imagn Images

Enact Plan B if Bellinger leaves

This offseason is becoming eerily similar to last year. Soto took the money to go to the Mets and Cashman had to pivot, and pivot he did.

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Cashman traded for Bellinger and Devin Williams while signing Max Fried. The GM’s moves worked and helped the Yankees tie the Blue Jays for the best record in the American League. Now, what could Cashman do for an encore?

If the Yankees can’t re-sign Bellinger, Cashman needs to be ready to enact his Plan B. Whether that’s signing Kyle Tucker or trading for an outfielder like Steven Kwan, the longtime GM has to show the fans that if Bellinger doesn’t come back, the outfield will be just fine.

Cashman has to be creative; he’s done it before, and he may need to do it again. Hopefully, he’s prepared.

Fill out the bullpen

Two moves the Yankees have made this offseason are re-signing Ryan Yarbroughand picking up Tim Hill’s option, which helps fill holes in the bullpen, but there’s still work to be done.

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Devin Williams is gone and Luke Weaver is still a free agent. Cashman and the organization have been great at creating a bullpen in the past and I expect this year to be the same. Perhaps a reunion with Weaver is on the way, or signing former Padres closer Robert Suarez to pair with David Bednar is a possibility. And, who knows, perhaps a trade could happen in the same way Williams was acquired.

Figuring out the outfield is the priority for the Yankees, but finishing up the bullpen is second on the list and Cashman needs to address it soon.

Oct 4, 2025; Toronto, Ontario, CAN; New York Yankees pitcher Luke Weaver (30) throws in the seventh inning against the Toronto Blue Jays during game one of the ALDS round for the 2025 MLB playoffs at Rogers Centre.

Oct 4, 2025; Toronto, Ontario, CAN; New York Yankees pitcher Luke Weaver (30) throws in the seventh inning against the Toronto Blue Jays during game one of the ALDS round for the 2025 MLB playoffs at Rogers Centre. / Nick Turchiaro-Imagn Images

Get greedy and sign a starter

The Yankees’ starting rotation is set … when it’s healthy.

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Gerrit Cole and Carlos Rodon will miss the start of the 2026 season, but they will be back. But there may be questions about their effectiveness when they do return. Cashman and the Yankees also have to wonder if they can fully trust the trio of Luis Gil, Will Warren and Cam Schlittler for another season.

The Yankees can give themselves some comfort by splurging on another starter either in free agency or via trade.

There are some intriguing buy-low, reclamation projects like Zac Gallen or Merrill Kelly who can shore up the back of the rotation. Miami has controllable starters like Sandy Alcantara and Edward Cabrera that can be traded for as well. The rotation is definitely low on the list of priorities for the Yankees, but with so many question marks, it can’t hurt to have as many starters as possible and if Cashman brings one in, the younger arms become trade pieces for the aforementioned outfielder.

Dispel all payroll questions

Heading into the Winter Meetings, there’s been a lot of chatter about the Yankees’ 2026 payroll and whether or not Hal Steinbrenner is willing to go over $300 million, including comments from Steinbrenner himself. They currently sit at around $283.6 million (after taxes), so there’s not a lot of wiggle room for the Yankees if they hope to improve their team.

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I find it hard to believe the Yankees would operate below $300 million, so Cashman could show the baseball world — and Yankees fans — that they are ready to spend this offseason by signing a Bellinger or a handful of names. Not to rush the process, but leaving the Winter Meetings without a deal done would not quell fears. It’ll be even worse if targets like Bellinger and Tucker sign elsewhere.

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The winter meetings are just days away, and the tentpole event of the MLB offseason usually provides plenty of movement via trades and free-agent signings.

Going into next weekâ€s events in Orlando, Florida, some teams are under more pressure than others to make a significant move or risk being left on the outside looking in at the offseason action.

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Here are the four teams under the most pressure at this yearâ€s winter meetings.

Chicago Cubs

No one seems to know what the Cubs want to be, including the Cubs themselves. Around this time last year, they were preparing to put a package together to acquire this yearâ€s biggest free agent, Kyle Tucker. Now, after a successful season with Tucker that included winning the NLâ€s top wild-card before being bounced by the Brewers in the NLDS, the expectation is that the outfielderâ€s time in Chicago is over.

If thatâ€s the case, the Cubs are back to where they were last year, with more questions in their lineup than answers. And itâ€s not just their lineup that needs some reinforcements; their rotation needs help as well.

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But beyond the need to add, the pressure on Chicago comes from the fact that the organizationâ€s desire to spend has come into question in recent years, as the ownership group has pulled back from being near the top of the league in payroll. This fall, Cubs fans finally saw their team get back to the NLDS for the first time since 2018, and theyâ€re tired of hearing about the players the team almost signed.

Next week, GM Jed Hoyer and Co. will have all eyes on them, waiting for a big move at the winter meetings.

Bryce Harper's Phillies and Aaron Judge's Yankees are among the teams under the most pressure this winter.

Bryce Harper’s Phillies and Aaron Judge’s Yankees are among the teams under the most pressure this winter.

(Jonathan Castro/Yahoo Sports)

New York Yankees

Last winter, after losing Juan Soto to the crosstown rival New York Mets, the Yankees pivoted to Cody Bellinger, who filled the void admirably with a strong 2025 campaign. The former MVPâ€s impact on New Yorkâ€s season was significant, as he was not only strong defensively but also provided lineup protection for AL MVP Aaron Judge. This winter, the Yankees could once again lose a pivotal part of their lineup, as Bellinger is one of the best position players available in free agency.

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Beyond the question of bringing back Bellinger, the Yankees need to add a first baseman and reinforcements in the back end of their bullpen. Right-hander Devin Williams signed a three-year, $51 million deal with the Mets earlier this week, and mainstay Luke Weaver is currently a free agent.

The Yankees havenâ€t made any significant moves yet this offseason. GM Brian Cashman was extremely active at the winter meetings in 2024, and it wouldnâ€t be shocking to see his team making moves again this year.

Detroit Tigers

The clock is ticking on the Tigers and their time with two-time AL Cy Young Award winner Tarik Skubal. It seems impossible to think Detroit would trade the best pitcher in the world, but reports have indicated that could happen, as theyâ€ve at the very least entertained calls on their ace, who will be a free agent after next season. In that case, the biggest question is how do you get enough value in return for a player of Skubalâ€s caliber, even with just one year of club control remaining?

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After a long rebuild, the Tigers reached the postseason in back-to-back seasons and seem to have a promising future ahead of them. So after all it took to get here, why not extend Skubal? There has been no better pitcher in baseball over the past two years than the Tigers†ace, and no matter the return, you will not be able to replace the type of pitcher Skubal is and the impact he can have on a playoff series. The problem, of course, is money, as the two sides are reportedly more than $100 million apart in extension talks.

If the Tigers know theyâ€re not going to find common ground with Skubal, it would be good business to shop him around and see what other teams might offer. Still, that doesnâ€t feel like the ending either side was hoping for in this situation.

Philadelphia Phillies

On the surface, the Phillies might not seem like a team under a lot of pressure. Over the past five years, theyâ€ve been one of the most aggressive and successful teams in baseball, building a core of talented players on long-term deals and reaching the postseason the past four Octobers. But the Phillies havenâ€t been able to get to the mountaintop, despite advancing to the World Series in 2022 and the NLCS in ‘23.

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Now Philadelphia has real decisions to make regarding the future of its roster, as three major contributors to the teamâ€s recent success are free agents: NL MVP runner-up Kyle Schwarber, left-hander Ranger Suárez and catcher J.T. Realmuto.

The priority for the Phillies this offseason is undoubtedly Schwarber, who is coming off the best season of his career and has been a leader in the Philadelphia clubhouse since he arrived in 2022. It would be devastating for the franchise to lose a guy like that, one of the most respected players in baseball and a fan favorite.

Outside of Schwarber, what moves does president of baseball operations Dave Dombrowski have up his sleeve? Even if the Phillies re-sign Schwarber, their roster has some other needs in the lineup and bullpen. The front office has the resources to address them, but theyâ€ll need to work quickly. With the roster getting older and the National League only getting better, Phillyâ€s window could be closing.

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Both New York clubs are searching for starting pitching this offseason, and two players they are reportedly strongly considering are Tatsuya Imai and Michael King.

The Mets and Yankees are among the most interested in the free agent righties, according to Mark Feinsand of MLB.com.

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That certainly doesnâ€t come as a surprise, as both would present a strong addition to either clubs rotation.

Imai, who was posted by the NPBâ€s Seibu Lions this offseason, is coming off a spectacular campaign in which he pitched to a career-best 1.92 ERA and 0.89 WHIP in 163 innings.

His plus-arsenal includes a mid-90s fastball, a splitter, slider, and cutter.

He has until Jan. 2 to sign with a club, and according to a recent report from the Athletic, he is expected to visit with teams upon the end of next weekâ€s Winter Meetings.

Boston, Philly, and the Cubs are also believed to be interested as well.

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King was tremendous in 2024 as he transitioned from the bullpen to a full-time starter, but he battled injuries for most of last season and was limited to just 15 outings with the Padres.

He dealt with a nerve injury in his throwing shoulder, and also lost time due to a knee injury.

The NY native and former Yankee has top of the rotation potential when healthy, but concerns over his durability could result in him landing a short-term deal this offseason.

King could potentially bet on himself with an eye on hitting the market again next winter, but there are several other clubs in the mix for his talents including the Orioles, Tigers, and Marlins.

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So letâ€s say – speaking hypothetically, Hal – the Yankees do indeed lower their payroll heading into the 2026 season. Obviously, they still intend to contend and they probably have enough talent to be a playoff threat.

But what would their winter look like if they forgo spending mega free agent dollars and work to improve on the margins only? They of course will reap benefits from an eventual Gerrit Cole return to an already-plus rotation, in addition to the usual Aaron Judge awesomeness and a roster with other strong points.

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Even so, they could use a Cody Bellinger return, bullpen fortification, a righty, defense-first first baseman and perhaps a stop-gap starter. Maybe a utility player, too.

How does that all work in an offseason in which the owner, Hal Steinbrenner said, “Would it be ideal if I went down (with the payroll)? Of course. But does that mean itâ€s going to happen? Of course not. We want to field a team we know could win a championship, or we believe could win a championship.â€

With that in mind, here are some suggestions for the Yankees if we remove boldface free agent names such as Bellinger and Kyle Tucker from their options.

Yeah, we know fiscal restraint doesnâ€t fit some folks†“Act like the Yankees and spend big†worldview, but this is just one potential spending scenario in a Hot Stove winter where all things are possible. Heck, maybe it means theyâ€re saving it up for next winter and a free-agent run at Tarik Skubal. Oh, now youâ€re interested.

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Outfield options

This is easy. They want Bellinger back, but heâ€s so versatile and so skilled in multiple baseball departments that heâ€s in high demand. For instance, Met fans would love it if he were another Yankee relocation to Queens. So if Bellinger goes elsewhere, what do the Yanks do on the grass?

Nothing.

Not sexy, we know. Signing Tucker would bring sizzle. But that might be $100 million more than whatever Bellinger costs. If the Yankees are trying to tamp down the payroll, they have choices here. Judge plays right, Trent Grisham, who accepted the qualifying offer, is back in center and Jasson Domínguez and/or top prospect Spencer Jones figure it out in left field.

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Swing-and-miss is a part of Jones†game, yes. But so is admirable athleticism and dizzying power. He had a .932 OPS and 35 homers across two minor league levels last season. Might be time to find out what heâ€s got.

“The Martian†might not have had the otherworldly (get it?) rookie season Yankees fans would have wanted. But Domínguez was once the most-hyped prospect in the world and one season doesnâ€t say it all about his career. Might be time to find out what heâ€s got, too.

If the Yanks do re-sign Bellinger, they could put Jones, Domínguez, and perhaps even Grisham into the trade carousel to address other needs.

Pitching ponderables

With Cole and Carlos Rodón both starting the season late, the Yanks need rotation depth to add to Max Fried, Cam Schlittler, Luis Gil and Will Warren. They re-signed Ryan Yarbrough, who will help, and could examine other lower-level free agents, too.

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Weâ€re thinking of names such as Tyler Mahle (2.18 ERA in 16 starts with Texas last season). The righty allowed only five homers in 86.2 innings and home run suppression skills could help in Yankee Stadium. Righty Adrian Houser revived his career with 11 sharp starts with the White Sox, though he had less success after a trade to the Rays.

Tampa Bay Rays starting pitcher Adrian Houser (37) throws a pitch against the Boston Red Sox in the first inning at George M. Steinbrenner Field

Tampa Bay Rays starting pitcher Adrian Houser (37) throws a pitch against the Boston Red Sox in the first inning at George M. Steinbrenner Field / Nathan Ray Seebeck – Imagn Images

Across their history, the Yanks have thrived at bringing in older stars who made their name with other teams, dating way back to the days of Johnny Mize or Enos Slaughter. Could they do it with one from this duo of the Cooperstown-bound ageless hurlers Max Scherzeror Justin Verlander? Might be a fun one-year deal for either.

As for the bullpen, the Yankees have vacancies left by Devin Williams and probably Luke Weaver, who is a free agent. The club has been really good at finding and developing useful relievers who might not be household names. They got mileage out of Ian Hamilton, for instance, and Clay Holmes bloomed under their tutelage. Do they have a few more in the pipeline?

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Maybe they go that route again. If not, there are plenty of potentially-useful relief arms available and they wouldnâ€t be top-of-the-market outlays, including Kyle Finnegan and Michael Kopech. Could they revive former Jays closer Jordan Romano, who is coming off two poor seasons?

Also, several of the Yankees†most highly-regarded prospects are pitchers, including 22-year-old Elmer Rodriguez, who got to Triple-A for one start last season and had a 2.58 ERA in 150 innings over three levels. Could the kids figure as inexpensive options or trade fodder?

Bench marks

A righty-hitting complement to Ben Riceat first base would be a nice pickup — someone who can help school the slugging Rice on the defensive nuances of the position. Paul Goldschmidt redux?

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Signing a utility player would fortify the bench, too. They liked Amed Rosario last season for his righty bat and he can provide coverage in the infield and outfield.

So could free agent Willi Castro, a coveted utility man last trade deadline. The switch hitter fizzled after going from the Twins to the Cubs, but he has experience at every position but catcher and first base.

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The Yankees‘ outfield is currently in flux and top prospect Spencer Joneshopes to be in the mix when the team breaks camp next March.

Jones, 24, had his breakthrough season in 2025, demolishing Double-A pitching before being promoted to Triple-A Scranton/Wilkes-Barre, where the outfielder held his own.

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Through both levels of the minor leagues in 2025, Jones slashed .274/.362/.571 with an OPS of .932. He also had 35 home runs and drove in 80 runs.

“Being able to be more consistent month-to-month, that was the biggest thing for me,†Jones told SNYâ€s Michelle Margaux at the Italian American Baseball Foundation Gala in the Bronx on Thursday night. “A lot of confidence and something I look forward to bringing in next year.â€

It was a bounce-back season for Jones, who struggled in 2024 once he got to Double-A. He credits a change in his swing for his consistency and continues to work on it this offseason in preparation for spring training.

“I changed some stuff with my swing, learned a lot about it and going into this offseason is just cleaning up some of the things that went wrong and moving into this next season,†he said.

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Outside of Aaron Judgein right field and Trent Grisham — who accepted the qualifying offer — in center, the Yankees have an opening in left field after the departure of Cody Bellinger. While the Yankees continue to try and bring Bellinger back, itâ€s not a guarantee, which gives Jones and other youngsters like Jasson Dominguez a chance to win the job this spring.

GM Brian Cashman said Jones “put himself in the conversation” to make the roster at the Yankees’ end-of-season news conference in October, and the outfield prospect is getting ready to earn it.

When asked what he could do to prepare to compete for a roster spot, Jones described his mindset.

“Trying to prove to them, every reason why you should be there,†he said. “Being as competitive as possible and showing them how bad you want it is important and thatâ€s going to be my job going into camp.â€

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Here’s the latestYankees free agency and trade buzz during the 2025-26 MLB offseason…

Dec. 4, 11:42 a.m.

While other suitors are certainly in the mix, Cody Bellingerremains the Yankees’ No. 1 target, and the club is making a “big effort” to bring him back, according to Jon Heyman of the New York Post.

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Heyman lists the Mets, Phillies, Angels, and Dodgers as other possibilities.

ESPN’s Jeff Passan has previously reported that signing Bellinger would be a “multipart move” for the Yankees, as the club would almost certainly need to move one of their other outfield pieces –potentially Jasson Dominguez or up-and-coming prospect Spencer Jones.

With Trent Grisham accepting the qualifying offer, the Yanks would have a surplus of outfielders if Bellinger was to re-sign.

Dec. 3, 8:22 p.m.

The high-stakes bidding war for Kyle Tuckerofficially includes one of the Yankees’ division rivals, as the superstar outfielder visited the Blue Jays’ facility in Florida on Wednesday, according to a report from Robert Murray of FanSided.

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It’s no surprise the reigning AL champions are big-game hunting for a new bat. The club signed free-agent starter Dylan Cease to a massive seven-year, $210 million deal and right-hander Cody Ponce to a three-year, $30 million contract in the last week.

Murray reports the Blue Jays are also interested in retaining shortstop Bo Bichette, who could garner an average annual value above $20 million.

Tucker would make the Blue Jays’ lineup even more imposing. In his lone season with the Cubs, the 28-year-old slashed .266/.377/.464 with 22 home runs and 25 steals. His seven-year run with the Astros was far more impressive, though — he hit .274 with 125 homers and 417 RBI.

Only time will tell if the Yankees make a legitimate run at Tucker’s services. His contract demands seem too rich for their blood, and the Yankees have stated they’re focused on re-signing Cody Bellinger, who’d come at a much lower price.

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Dec. 1, 9:19 a.m.

The Yankees re-signing Cody Bellinger would be a “multipart move,” reports Jeff Passan of ESPN.

Per Passan, the Yanks are unlikely to enter the season with Bellinger, Aaron Judge, Trent Grisham, Jasson Dominguez, and Spencer Jonesall on the team.

Things got tight player-wise and payroll-wise for New York when Grisham accepted the one-year qualifying offer.

Another factor when it comes to Bellinger or other large signings/trades for the Yanks this offseason is that with Grisham now in tow, New York’s payroll for 2026 is already roughly $278 million.

Pair the above with owner Hal Steinbrenner‘s recent comments that it would be “ideal” to lower payroll for this coming season — and his repeated statements about not wanting to carry a payroll above $300 million — and it’s fair to wonder how much wiggle room there will be to retain Bellinger and address other needs.

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Nov. 20, 9:37 a.m.

The Yankees and Devin Williams‘ representatives recently discussed the possibility of the reliever returning to the Bronx, per Ken Rosenthal and Will Sammon of The Athletic.

In addition to the Yanks, Williams has reportedly drawn interest from the Mets, Dodgers, and Blue Jays, among others, this offseason.

The Yankees recently re-signed left-hander Ryan Yarbrough, but their ‘pen is still in need of serious reinforcements.

In addition to Williams, Luke Weaver is also a free agent.

Nov. 13, 11:09 a.m.

The Red Sox are among the teams with interest in Devin Williams, reports Will Sammon of The Athletic, who also lists the Dodgers and Reds among teams that have expressed interest.

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Fabian Ardaya of The Athletic also reported on Los Angeles and Williams, saying there appears to be mutual interest.

Los Angeles was one of the teams exploring the possibility of dealing for Williams last offseason before he was traded to the Yankees.

Williams, 31, struggled last season for the Yanks, posting a 4.79 ERA and 1.12 WHIP in 62.0 innings.

While Williams was not his regular elite self, his stuff still played up as he had a strikeout rate of 13.1 per nine.

In addition to Williams, Luke Weaveris also a free agent, leaving the back end of New York’s bullpen in an uncertain spot.

Nov. 12, 11:33 a.m.

A source told Gary Phillips of the New York Daily News that the Yankees have checked in on left-hander Ryan Yarbrough, and the club is “expected to be suitors” for the 33-year-old.

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After signing with the Yanks last spring, Yarbrough ended up being a valuable and versatile piece for Aaron Boone‘s pitching staff. He started eight games and appeared in 19 games in total, pitching to a 4.36 ERA while holding opposing lefties to a .198 batting average.

Yarbrough did miss a significant chunk of the season, though, as an oblique injury kept him out from mid-June to early September. As a result, he was left off the Yankees’ postseason roster.

Nov. 11, 3:45 p.m.

Historically, the Yankees have been among the highest-spending teams in baseball, but owner Hal Steinbrennerand GM Brian Cashmanhave reiterated multiple times over the past couple of years that having a payroll over $300 million is “simply not sustainable for us, financially,” as Cashman put it.

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“It wouldnâ€t be sustainable for the vast majority of ownership [groups], given the luxury tax we have to pay,” Cashman said last May. “Iâ€ve been a broken record [on this topic]: I donâ€t believe I should have a $300 million payroll to win a championship.”

So how does that line of thinking impact what the Yankees will do this offseason?

Appearing on “Pinstripe Post,” Joel Sherman of the New York Post laid out how he believes the Yankees can thread the needle to retain a key free agent like Cody Bellinger, whom he referred to as “the key to their offseason,” while lowering their payroll beneath the $300 million number.

“I think the goal this offseason is to try to get under $300 million, luxury tax money. I think within that theyâ€d like to re-sign Cody Bellinger, add another reliever who can pitch in the final six outs of the game… I think theyâ€d like to find a complementary starting pitcher to help them through some injuries early in the season. I think theyâ€d love to flip J.C. Escarra for a righty version of J.C. Escarra… and I think theyâ€d like to find a complementary right-handed bat, and maybe plus Amed Rosario, who they liked a lot and tried in previous years to get.

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“That all told, I think the Yankees would feel, if they got the versions of the players they wanted to, they would feel thatâ€s a 90+ win team, and theyâ€d have a shot to line it up, and that they could do that in the high ($200 millions).”

The Yankees ended last season with a payroll of $323.7 million, for luxury tax purposes. Factoring in projections for arbitration eligible players and other players in their pre-arbitration years who are still under team control, the Yankees currently have a payroll of roughly $244 million.

Can the Yankees fit in a player like Bellinger, who is projected to make somewhere around $27 million per season, and still make other needed moves while staying under the $304 million luxury tax threshold?

If that is indeed the goal, while it does appear possible, there doesn’t seem to be a lot of wiggle room.

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Red Sox pitcher Sonny Gray apparently is looking forward to taking on his new team’s biggest rival, saying he’s happy to be in “a place where it’s easy to hate the Yankees.”

The Red Sox acquired the well-traveled Gray in a trade with the Cardinals last week, adding the durable pitcher to a starting rotation that was thin on options during Boston’s postseason ouster in New York.

Gray already is familiar with the Red Sox-Yankees rivalry after spending parts of two seasons in the Bronx earlier in his career, and the three-time All-Star didn’t mince words when discussing his experience in New York.

“It just wasn’t a good situation for me,” Gray told reporters Tuesday. “It wasn’t a great setup for me and my family. I never wanted to go there in the first place.”

Sonny Gray struggled to a 4.51 ERA — nearly a full run higher than his career numbers — during his time with the Yankees. “It wasn’t a great setup for me and my family,” he said. “I never wanted to go there in the first place.” Brad Penner-USA TODAY Sports

That clearly wasn’t the case for Gray with the Red Sox, who needed the right-hander to waive his no-trade clause in order to complete their deal with the Cardinals.

“What did factor into my decision to come to Boston — it feels good to me to go to a place now where, you know what, it’s easy to hate the Yankees,” he said. “It’s easy to go out and have that rivalry and go into it with full force, full steam ahead. I like the challenge.”

Gray struggled to a 4.51 ERA — nearly a full run higher than his career numbers — during his 41-game run with the Yankees in 2017 and 2018. New York acquired Gray in a blockbuster deal with the Athletics only to trade him less than 18 months later to Cincinnati, where he began reviving his career with the Reds.

“When that was happening, and we were in Oakland and getting traded — that was a long time ago — I never wanted to go [to New York],” Gray said. “So then I was there, and it just didn’t really work for who I am. … I just wasn’t myself. I just didn’t feel like I was allowed to go out there and be Sonny.”

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Gray, 36, has a 3.58 ERA over a 13-year career with the Athletics, Yankees, Reds, Twins and Cardinals. He joins a Red Sox rotation that is led by ace Garrett Crochet but also features a handful of unproven candidates after right-hander Brayan Bello.

Gray is the latest Red Sox pitcher to publicly say that he didn’t enjoy playing for the Yankees.

Star closer Aroldis Chapman said earlier this offseason that he would “retire on the spot” before playing for New York again, adding that he “dealt with a lot of disrespect” from Yankees management.

Gray, who is 66-50 with a 3.51 ERA in seven seasons since leaving the Yankees, acknowledged that he learned a great deal from his time in New York.

“I’ve been a better baseball player, husband, everything from having that experience and going through that,” he said.

Boston’s first series with the Yankees next season will be April 21-23 at Fenway Park. The Red Sox play their first series in Yankee Stadium from June 5 to June 7.

If he ends up pitching for the Red Sox in the Bronx, Gray hinted that things will be different.

“This time around, it’s just go out and be yourself,” he said. “Don’t try to be anything other than yourself. If people don’t like it, it is what it is. I am who I am, and I’m OK with that.”

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Newly acquired Boston Red Sox starter Sonny Gray did not enjoy his time with the New York Yankees. Gray hasn’t really made it a secret that he wasn’t a fan of playing in New York, but he took his hate to another level during his introductory news conference with the Red Sox on Tuesday.

Gray immediately reignited the rivalry between himself and Yankees fans, saying, “It feels good to me to go to a place where it’s easy to hate the Yankees.”

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He later added, “I never wanted to go [to New York] in the first place.”

That should be music to the ears of all Red Sox fans.

While it’s not uncommon for athletes to pander to their new fan base, that’s not the case with Gray. He has spoken publicly a few times about why he hated playing for the Yankees. In 2019, he said the team wanted him to prioritize throwing sliders, something he said wasn’t a good fit for his pitch mix. He blamed the team for making him throw “a s***ty spinning pitch” more often than he was comfortable with.

Gray’s unease in New York came through in his numbers. After an excellent start to his career in Oakland, he was shipped to New York at the 2017 MLB trade deadline. While his ERA didn’t rise too much that first season, there were some troubling signs under the surface. Gray’s strikeout rate dropped, his walk rate increased, and he starting giving up a ton of home runs in the second half in New York.

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That came back to hurt him in a big way in 2018. The reduced strikeout rate and increased walk rate stayed, and Gray posted a 4.90 ERA over 130 1/3 innings with the Yankees. He eventually lost his spot in the rotation, finishing the year in the bullpen.

The Yankees had enough at that point, trading Gray to the Cincinnati Reds in the offseason. He immediately got his career back on track, making the All-Star Game in his first season with the Reds. Since then, Gray has generally performed like a top-of-the-rotation starter. He has a 3.51 ERA since leaving the Yankees, with two All-Star appearances. Gray even managed a second-place finish in Cy Young voting in 2023, when he was with the Minnesota Twins.

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The 36-year-old Gray has aged gracefully. His reliance on throwing a ton of pitches, many with different types of spin, has allowed him to stave off decline as he has gotten older. Despite an elevated 4.28 ERA last season, there were signs that Gray was unlucky and could show improvement in his first season with the Red Sox.

Boston obviously believes that’s the case, as it gave up two young pitchers to acquire Gray in November. Both the franchise and its fans probably feel even better after Gray spent his first moments with his new club denigrating its most hated rival.

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NEW YORK — For more than six decades, the Mets and Yankees have coexisted fewer than 10 miles apart across the East and Harlem Rivers. Because of it, theyâ€ve shared plenty of experiences, from the now-defunct Mayorâ€s Trophy Games to the 2000 Subway Series and other Interleague matchups.

They also share parts of their DNA. Entering the first matchup between the two clubs in 2026, 172 players have suited up for both the Yankees and Mets. Some were replacement level or otherwise forgettable, but a good many were significant players for one or both franchises.

By agreeing to a three-year deal with the Mets, according to a source, reliever Devin Williams is set to become the latest notable name to represent both franchises. Williams, who spent 2025 with the Yankees after a trade from the Brewers, continues a recent pipeline of talent from the Yanks to the Mets. Over the previous two offseasons, pitchers Luis Severino and Clay Holmes and superstar outfielder Juan Soto all signed with the Mets in free agency after wearing Yankees pinstripes.

Hereâ€s a look at some of the most prominent players to appear in both the Bronx and Queens:

No one has had as much success with both the Yankees and Mets as Cone, who contributed multiple All-Star seasons to each. Kansas Cityâ€s third-round pick in the 1981 MLB Draft, Cone came to the Mets in a steal of a trade, then proceeded to go 80-48 with a 3.08 ERA over the next six seasons. Multiple trades later, he wound up with the Yankees at the 1995 Trade Deadline.

In the Bronx, Cone reestablished his New York excellence, going 64-40 with a 3.91 ERA over six seasons, winning half a dozen playoff games and four World Series rings, tossing a perfect game and pushing himself to borderline Hall of Fame contention. Cone finally returned to the Mets as a free agent at the end of his career but didnâ€t last long at age 40. All told, he produced 20.3 WAR with the Yankees and 19.4 with the Mets.

While the Yankees and Mets can both lay claim to some of Coneâ€s finest seasons, Goodenâ€s exclusively occurred in Flushing. A teenage phenom, Gooden won the National League Rookie of the Year Award in 1984 and an NL Cy Young Award the following season, going 58-19 with a 2.28 ERA over a spectacular three-year stretch to open his career. Even as injuries and off-field demons began to interfere, Gooden still mustered successful seasons, winning 157 games with the Mets before his 30th birthday.

His tenure with the Yankees began only after he was suspended for the 1995 campaign. Despite being a shell of his former self by that point, Gooden became notable across town for the no-hitter he pitched in 1996 — easily the highlight of a sometimes-bumpy comeback story.

Another poster child of the late-80s Mets, Strawberry dominated during his time in Flushing, bursting onto the scene as the 1983 NL Rookie of the Year before reeling off seven consecutive All-Star appearances. He hit between 26 and 39 home runs each year, leading the league in that category in ’88. In so doing, he became — like Gooden — one of the most important players on the Mets†’86 World Series championship team.

Also like Gooden, Strawberry battled demons off the field, but Yankees owner George Steinbrenner was willing to give him a chance at the end of his career. By that point, Strawberry was no longer the force he had once been in Queens, but he stuck around long enough to win three more World Series rings, even clubbing three home runs during a dynamic performance in the 1996 American League Championship Series.

Juan Soto
Yankees: 2024
Mets: 2025-present

Soto spent only one season in the Bronx, but it sure was a memorable year. The prize of a blockbuster trade between the Yankees and the Padres, the outfielder batted .288 with 41 home runs and a .989 OPS for the Bronx Bombers in 2024. He provided a massive postseason moment as well, belting a go-ahead, three-run home run in extra innings of Game 5 of the ALCS against the Guardians to send the Yankees to the World Series.

Despite the Yanks’ push to retain Soto, he opted to sign with the Mets on a 15-year, $765 million megadeal — the largest contract in MLB history. After a bit of a slow start to his first season in Queens, Soto had a torrid June (1.196 OPS) and was excellent from August onward to finish the year with a .263/.396/.525 slash line. Under contract through his age-40 season, Soto will be tasked with leading the Mets to at least one World Series title — something he accomplished at age 20 with the Nationals.

Unlike many others on this list, most of Venturaâ€s best years didnâ€t occur in New York at all, but instead in Chicago. Heâ€s best known in Queens for his walk-off “grand slam single†in 1999 NLCS Game 5, though Ventura was about far more than that single iconic moment. His â€99 season was the best of his career, as Ventura hit .301/.379/.529 with 32 homers and 120 RBIs to finish fourth in NL MVP voting. When the Mets dealt Ventura to the Yankees for David Justice after the 2001 season, it was one of the rare prominent trades between those two organizations. Justice never took the field for the Mets, who dealt him to the Aâ€s a week later, but Ventura gave the Yankees an All-Star season in 2002.

Hernandez is the first player on this list who was clearly more prominent in the Bronx than Queens. A key international signing before the 1998 season, “El Duque†won 49 games over his first three regular seasons and postseasons with the Yankees, winning three World Series titles in the process. Renowned for his abilities under pressure, Hernandez went a remarkable 7-0 with a 1.22 ERA over his first eight playoff starts, averaging more than seven innings per outing. He signed with the Mets before the 2006 season and enjoyed a fine first summer across town, but a calf injury suffered on the eve of the postseason prevented him from adding to his postseason successes.

Beltrán spent much of the prime of his career in Flushing, contributing four All-Star seasons as he mostly made good on the seven-year, $119 million deal the Mets offered him to come to New York. Criticism has always followed Beltrán for the called strike three he took to end the 2006 NLCS, but his overall production level was high — and the Mets were able to trade him for Zack Wheeler at the end of his contract. Years later, at age 37, Beltrán extended his career as a solid regular for the Yankees, chasing a ring there for three seasons before finally receiving one with the Astros in ’17.

From 2011-12, Granderson hit 84 home runs with the Yankees, taking advantage of the new ballparkâ€s short porch in right field — a paradise for left-handed sluggers, unlike his old home at spacious Comerica Park in Detroit. Grandersonâ€s strong performances, along with his reputation as a caring teammate and clubhouse presence, prompted the Mets to sign him as a free agent after his contract expired. While he wound up being a shade less productive across town, Granderson nonetheless was a positive contributor on and off the field, particularly during the Mets†World Series run in ’15.

Another player better-known for his time elsewhere — in this case, Oakland — Henderson nonetheless stole 326 of his record 1,406 career bases with the Yankees, and 42 with the Mets after turning 40. Henderson was still very much in his prime during his time in the Bronx, clubbing 78 home runs with the Yankees and posting an .850 OPS as he bolstered his Hall of Fame resume. Henderson later served as a first-base coach and baserunning instructor in the Mets organization.

Al Leiter
Yankees: 1987-89, 2005
Mets: 1998-2004

Statistically, Leiter was one of the finest pitchers in Mets history, which takes some doing in an organization that has produced Tom Seaver, Jacob deGrom, Jerry Koosman, Gooden and others. Leiter produced 28 WAR and a 124 ERA+ over his seven seasons in Flushing. He wasnâ€t as effective as a youngster coming up with the Yankees, nor during his cameo back in the Bronx in 2005.

Randolph would barely be remembered for his brief Mets tenure if not for the fact that he also managed the team from 2005-08, overseeing one of the most fruitful periods in franchise history but also two memorable September collapses. As a player, Randolph was all Yankees, serving as captain for three seasons, hitting .275 and stealing 251 bases.

Put Berra in the same category as Randolph. A Yankee for nearly his entire Hall of Fame career, Berra signed on with the Mets as a 40-year-old coach in 1965, but he actually made four appearances as a player. Berra wound up the Mets†manager for five seasons during the 1970s, winning the NL pennant in ’73.

One of the most productive second basemen in Yankees history, Canó developed into a star during its “Core Four†era, making five All-Star teams and winning a World Series title in 2009. Six years after signing as a free agent with the Mariners, Canó returned to New York in Brodie Van Wagenenâ€s oft-criticized first trade as general manager, which looked even worse after Canó received a one-year suspension for a PED violation following the 2020 season. Canó returned to the Mets in 2022 but was released after just 12 games before making appearances with the Padres and Braves.

Colonâ€s lone season with the Yankees helped him revive his career following a series of injuries, but his three-year stint with the Mets turned him into a cult hero. It was with the Mets that Colon became one of the most successful 40-something baseball players of the modern era, winning 44 games with a 3.90 ERA. His bullpen cameo in the 2015 postseason was helpful; his home run in San Diego in 2016 was legendary.

Other noteworthy players to appear for both the Yankees and Mets: Bobby Abreu, Armando Benítez, Dellin Betances, Rick Cerone, Tony Clark, Tyler Clippard, Todd Frazier, Clay Holmes, Dave Kingman, Lee Mazzilli, Bob Ojeda, John Olerud, Jesse Orosco, David Robertson, Gary Sánchez, Luis Severino, Gary Sheffield, Mike Stanton, Ron Swoboda, Ralph Terry, Todd Zeile.

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The New York Mets have agreed to a three-year contract with former Yankees closer and two-time All-Star reliever Devin Williams, Yahoo Sports’ Russell Dorsey confirms.

The Athleticand ESPN first reported the news. Per ESPN’s Jeff Passan,the contract is worth more than $50 million in guaranteed money.

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Williams, 30, was one of baseball’s best relievers during a six-year stint with the Milwaukee Brewers. He made two All-Star teams while posting a 1.83 ERA with 375 strikeouts and 112 walks in 235 2/3 innings pitched during his Brewers stint. He took over as closer in his last three seasons in Milwaukee and recorded 68 total saves.

The Yankees acquired Williams and his airbender changeup in a blockbuster trade last offseason, sending pitcher Nestor Cortes Jr., infield prospect Caleb Durbin and cash in return to Milwaukee. Williams now leaves the Yankees to join the crosstown rival Mets after a disappointing season in the Bronx.

Williams, 31, struggled out of the gate with the Yankees and was demoted from his closing job after 10 games. His performance improved over the summer, and he regained the role later in the season, but he finished the campaign with a career-worst 4.79 ERA and 1.129 WHIP while tallying 18 saves in 62 innings pitched. He closed 29 of the 67 regular-season games in which he appeared.

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Williams finished the regular season strong. He didnâ€t allow a run in 22 of his final 23 outings and pitched four scoreless innings in the postseason for the Yankees. The Mets will certainly be hoping that version of Williams shows up in Queens.

The Mets are signing Williams as veteran closer Edwin Díaz is also a free agent. A reunion between Díaz and the Mets remains possible, but the three-time All-Star, who was at his best this past season, is expected to command a lucrative contract on the open market. Williams is Yahoo Sports’ No. 27 free agent this winter. Díaz is ranked No. 11.

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