This is part one of a two-part series predicting offseason moves for the New York Yankees. Part one focuses on free agency and arbitration decisions.
Though the 2026-27 MLB offseason officially started after the Brewers won their first World Series title in team history last Wednesday, chances are it won’t last long. At least, the first segment of it.
It is something of an inevitability that when the clock strikes midnight on Dec. 2, MLB will enter a lockout when the collective bargaining agreement between MLB and the MLB Players Association expires.
The last time that happened was in the 2021-22 offseason and the lockout lasted 99 days.
An added wrinkle this time around is one of the main issues expected to be discussed is the possible implementation of a salary cap and floor, one which could cause significant change in the way clubs choose to retain their free agents, let alone acquire outside talent. It might even mean the Yankees could be looking to shred salary by the time the work stoppage concludes.
Still, clubs will still have a month to operate before these changes even have a chance at becoming a reality. With that in mind, let’s look at the in-house decisions the Yankees will have to make.
Free Agents: Yankees players set to reach free agency include David Bednar, Paul Blackburn, Jazz Chisholm Jr., Michael Fulmer, Paul Goldschmidt, Trent Grisham, Tim Hill, Amed Rosario, John Schreiber and Ryan Yarbrough.
Bullpen mates Bednar and Blackburn should be the Yankees’ top priorities when it comes to retention in the early days of the offseason.
Bednar was about as solid as a closer can get, converting on 35 of 39 save opportunities with strong underlying numbers. Blackburn posted 1.69 ERA across 62 games and 85 innings.
Brent Headrick was the only other bona fide option in the bullpen come postseason time, meaning the Yankees severely need to bolster their bullpen this winter. Retaining the pair of free agents is a potentially crucial start.
The Yankees offered the $23.15 qualifying offer to Bednar, though coming to terms on a longer-term deal with a lower average annual value would be mutually beneficial. Bednar needs to decide whether to accept or reject the offer by Nov 17.
Speaking of the qualifying offer, Grisham accepted the Yankees’ $22.025 QO last offseason and quickly outwore his welcome, missing time with a right hamstring strain and posting a .703 OPS when healthy. The center fielder, who will turn 30 years old on Nov. 1, also graded out negatively on defense for the second-straight season. While many predicted his 34-home run breakout in 2025 was a mirage, bringing back Grishman was the biggest blunder of last offseason. Don’t expect them to make this same mistake again.
Chisholm Jr. is another player who has served the Yankees well for a time but saw his free agent stock take a dip with a down contract year. While Chisholm Jr. has never been great against same-handed pitchers, he was a true platoon bat in 2026 after reaching base at just a .269 clip against left-handers. Couple that with a general lack of power, especially noticeable after the second baseman said his goal for the year was a 50/50 season, and a change of scenery may be best for both parties.
While the 28-year-old certainly has the talent and ability to bounce back, newly minted utility infielder Anthony Volpe could substitute for Chisholm Jr. next year for millions of dollars less.
Something of a figurehead for the “run it back Yanks,” New York brought Goldschmidt back on a second-straight one-year deal, even after watching his numbers nosedive following the 2025 All-Star break. The Yankees got more of the same in 2026 — a weakside platoon bat who mashed southpaws but was nearly unplayable against right-handers.
With Aaron Judge playing the majority of next season at 35 years old and oft-injured slugger Giancarlo Stanton still in the fold for one more season, the Yankees desperately need first baseman and MLB Postseason home run leader Ben Rice in the field. Even if deadline acquisition Luis García Jr. shifts back to the keystone for the first time in pinstripes, there’s no room for a third year of Goldschmidt in the Bronx.
Another veteran leader and weak side platoon bat, Rosario posted a robust .833 OPS against right-handers in 2026 but a below average .606 OPS against lefties and a .684 OPS overall. His defense graded out even worse, with Baseball Savant crediting Rosario with being worth -9 outs above average across second base, third base and the two corner outfield spots. The Yankees can get younger and cheaper while also finding more production from this bench spot.
Hill served the Yankees well over the past two and a half seasons, providing a durable rubber arm who stymied left-handed hitters. The 36-year-old would have been the consummate LOOGY a decade ago. Instead, his unsightly .293 batting average against versus righties in 2026 and his ERA jumping up by over a run make another reunion unlikely. Instead, the most enduring memory from his Yankees career will almost certainly be the what-if from Game No. 1 of the 2024 World Series.
Fulmer pitched poorly in 12 appearances for the Yankees and will be out the door unless Pitching Coach Matt Blake and his staff see something that the even the underlying numbers don’t.
Like Fulmer, Schreiber was a late season acquisition after being claimed off waivers from the Kansas City Royals. Unlike Fulmer, Schreiber was included on the postseason roster and has been a serviceable back of the bullpen arm for the past half decade. Still, it makes more sense for the Yankees to either upgrade in this spot or fill it with an optionable pitcher.
Yarbrough was essentially a replacement-level player in 2026, and a cheaper swingman could easily be found.
Re-signing predictions: Bednar (3 years, $47 million), Blackburn (2 years, $15 million)
Contract values based on Spotrac’s projected market value AAV.
Salary Arbitration: Players eligible for salary arbitration under the current model (with salary predictions) include José Caballero ($3.7 million), Fernando Cruz ($2.3 million), Luis García Jr. ($11 million), Luis Gil ($2.3 million), Heliot Ramos ($3.2 million), Clarke Schmidt ($4.5 million), Anthony Volpe ($4 million), Ryan Weathers ($3.1 million) and Austin Wells ($2.6 million).
The deadline for teams to offer players salary arbitration for 2027 is Nov. 20.
Caballero, García Jr., Ramos, Volpe, Weathers and Wells are clear locks to either receive an arbitration offer or settle prior to the hearings.
The other three bring injury concerns of varying degrees that place their roster spots in question.
Cruz ended the season on the 60-day injured list after being diagnosed with a partially torn ulnar collateral ligament in his throwing elbow. Cruz will also turn 37 years old just three days after 2026 Opening Day as it is currently scheduled. Opting for the non-surgical route for now, the Yankees would likely be willing to stomach the relatively cheap gamble if Cruz stays that course. If not, faced with a year-plus absence, the Yankees may cut bait, even if his 1.2 wins above replacement out of the bullpen would be missed sorely.
In his return from a 2025 internal brace procedure, Schmidt made just one appearance in September before heading straight back to the IL with a right bicep injury. A 2017 first round selection, Schmidt is now the second-longest tenured Yankee but hasn’t pitched in earnest in a year and a half. Almost $5 million for a question mark is pricey for a team already rostering at least six other arms outside of Schmidt worthy of being in a major league rotation.
Gil battled injuries and ineffectiveness in 2026, quickly falling out of favor and being sent down to Triple-A Scranton-Wilkes Barre in late April. The right-hander didn’t make it back up to the majors until the tail end of August after battling a shoulder ailment in the minors.
Though the 28-year-old isn’t exactly young, Gil is just two years removed from winning the American League Rookie of the Year award. Even if Gil has to reinvent himself as a reliever, there is probably still an ounce of value left in retaining the out-of-options pitcher for one more go-around.
Non-tender predictions: Schmidt
Arbitration estimates based on projections by MLB Trade Rumors Contributor Matt Swartz.