The New York Yankees' personnel decisions this offseason will be orchestrated by Brian Cashman. No need to beat around the bush. He'll still be here, weighing the finances, figuring out how to navigate all of his incumbent roadblocks after the Yankees' three-game sweep at the hands of the Tampa Bay Rays. Last winter, that involved leaving the bullpen bare-bones and asking Matt Blake to figure things out on the fly, while anchoring the offense to Trent Grisham's qualifying offer. $22 million accident or stroke of genius? You be the judge.
Blake handled things brilliantly, to his credit, and the Yankees managed to persist as the Yankees always seem to. 93 regular-season wins. A Wild Card Series statement against the Boston Red Sox, who've gone from unbeatable to the only team they can beat. A grace-free early exit and an offseason marred by theatrics and fireworks in the fandom.
The Yankees will likely lose plenty more pieces and replace them with replacement-level players. At first glance, these are the five Yanks who will absolutely be gone, either because they wore out their welcomes or priced their way out of town.
Two Honorable Mentions and Tough Decisions: This list nearly included both closer David Bednar and outfielder Jasson Domínguez. Ultimately, I landed on keeping Bednar, even as free agency looms; the team isn't foolish enough to enter next season without a bonafide closer (right? ... right?!), so they have to either pay or surrender assets for someone. It might as well be Bednar, who's expensive, but not exorbitant. Domínguez's trade value is at an all-time low, and while I'm sure the Yankees' faith in him - not all that high to begin with - has been shaken, it's impossible to calculate what they could actually receive for him. My estimation is he'll be gone midseason, but not during the offseason.
7 Yankees who won't be back after playoff mess vs. Rays led to an early offseason
Paul Blackburn, Reliever
Blackburn managed to outclass his proposed role by midseason and became the Yankees' multi-inning stopper, forming a nastry triumvirate with Bednar and Brent Headrick. He outperformed the $2 million contract he was given, which many fans assumed was a bizarrely redundant deal for a longman. With that in mind, he'll take to the open market - a weak free agent market where relief work is always in demand - and secure a multi-year payday (probably two seasons) at $10-12 million per. No longer a bargain, the Yankees will instead try to create the next Blackburn instead of paying this one. It's probably the right idea, but it won't be fun watching a bullpen pillar walk out the door and leave things even thinner.
Ali Sánchez, Catcher
Yes, the Yankees somehow made it all the way to the end of their season with Sánchez as their primary backup catcher. Their last-ditch attempt to bring in Mitch Garver in August never stuck, and the Yanks spent the final two months crossing their fingers they would've have to use Sánchez. Those are the perils of never actively seeking a right-handed upgrade. If he returns and the spot is left empty again, something has gone horribly wrong.
Tim Hill, Reliever
Is Ryan Yarbrough more than just a viable long relief option? Will he return? He seems comfortable, but there's always a chance someone may overpay for his 3.69 ERA in 63 1/3 frames. Regardless, the Yankees carrying Yarbrough on the postseason roster seems like curtains for the beloved Hill, whose stuff lost a tick or two this year, turning it from befuddling into below-average. He's a 36-year-old free agent, and it's a bummer things ended this way.
Jazz Chisholm Jr., Second Base
Chisholm Jr. ended this Yankees season in a puddle of mistakes, then hopped in front of the microphone to say he'd do it all again, if given the chance. He might get that chance. It won't be here. As hopes of 50-50 dissolved, Chisholm Jr. still rallied late to pair his excellent athleticism with a league-average offensive season. He'll be the second-most sought-after free agent second baseman behind Brandon Lowe in a staggeringly weak market.
How will the Yankees replace him? That's their problem. But Chisholm Jr. will surely be overpaid by some team looking to make a splash. The discount does not exist.
Fernando Cruz, Reliever
Let's keep this one short and sweet and sad. Cruz was a largely awesome Yankee who loved being here. He's also a 36-year-old reliever who's attempting to rehab a UCL tear instead of surgically repair it. The Yankees responded to his attempted comeback by placing him on the 60-Day IL. He'll be an emotionally taxing, but fairly easy, non-tender decision.
Paul Goldschmidt, First Base
The Yankees have collected DH/first basemen like talismans all season, rotating Ben Rice and Luis Garcia Jr. and likely needing room for some Aaron Judge first base reps next year. Goldy has been a consummate professional. Every time you thought he was done contributing, he found an additional layer. But he's 39 years old. The Yankees value flexibility and probably don't want to roster a lefties-only first base backup.
To be fair, we thought that last year, too. But this season, the decision might be Goldy's, especially headed towards a lockout. Go get that Hall of Fame plaque. Give the Yankees a cursory mention.
Trent Grisham, Center Field
The Yankees offered Grisham the qualifying offer prior to the 2026 season, betting that while they didn't love him as a long-term proposition after an inflated '25 campaign, they couldn't see an issue with a short-term, $22 million marriage. Grisham hurt his hamstrings, posted a 95 OPS+, lost sprint speed by the bowlful in center field, and couldn't buoy his season with as many bouts of occasional clutchness as he did in his second season with the Yanks. Bringing him back at any price would be malfeasance.
Besides, they're definitely keeping Ryan McMahon around. Can't afford two hefty financial anchors, in that case.
