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Spring training is almost here! Despite a winter that moved at a glacial pace, we’ve somehow already arrived at pitchers and catchers reporting to camp, the Yankees contingent arriving in Tampa on Wednesday. But before the warmer weather arrives, we ought to take one final look back at the business conducted by the Yankees during a frigid offseason and the man pulling the strings behind those decisions, general manager Brian Cashman.
The Yankees’ offseason began just over four months ago with their unceremonious dumping out of the ALDS at the hands of the Blue Jays. From that point forward, focus turned to 2026 and the calculus it would require to get the Yankees back to the playoffs. The team could boast a solid foundation of players — one which produced the best offense in baseball — and the question became whether to run in back and hope for better results vs. taking a more proactive approach to improving the roster.
Four months later, we know the answer to that question. Despite his public protests to the contrary, Cashman held firm to a policy of rolling the dice with largely the same group of players that fell well short of the ultimate prize in 2025, hoping that better luck might bring improved results. Let’s review the decisions he made before I hand the floor over to you to voice your opinions on the course charted by the front office.
Upon the conclusion of the World Series, eight players became free agents — Trent Grisham, Paul Goldschmidt, Devin Williams, Luke Weaver, Amed Rosario, Austin Slater, Ryan Yarbrough, and Paul Blackburn — with Cody Bellinger joining them a day later when he declined his player option for 2026. You’d be forgiven if you missed the Yankees’ opening moves of the offseason, the team picking up their club option on Tim Hill while declining the option on Jonathan Loáisiga. In a similar vein, their first free agent signing was Yarbrough, retained on a one-year, $2.5 million deal to reprise his swingman role from 2025. The focus remained on the margins of the bullpen in the early weeks of November, the front office trimming the fat by non-tendering Mark Leiter Jr., Ian Hamilton, Jake Cousins, and Scott Effross.
Then came the Rule 5 Draft, the Yankees selecting righty pitcher Cade Winquest from the Cardinals while adding Spencer Jones, Elmer Rodríguez, and Chase Hampton to the 40-man roster to protect them from departing. “Operation: Run it Back” kicked into another gear as the Yankees focused on returning even the fringe role players from 2025, both Rosario and Blackburn re-signed on one-year pacts. Shortly thereafter, the Yankees came to agreements with all of their remaining arbitration-eligible players — Clarke Schmidt, Oswaldo Cabrera, Jazz Chisholm Jr., David Bednar, Anthony Volpe, Fernando Cruz, Camilo Doval, Luis Gil, José Caballero, and Jake Bird. (The final piece of the ”Run it Back” puzzle fell into place this past week with the reunion with Paul Goldschmidt for one year and $4 million.)
The first real contentious decision of the offseason actually occurred a few weeks prior to the arb calls, when the Yankees extended the $22.025 million qualifying offer to Trent Grisham. The 29-year-old center fielder accepted it pretty quickly. Focusing solely on the player, one could make the argument that it’s a high-reward, low-risk move — he either repeats his career year from 2025 and plays for a relative bargain, or he regresses in which case he’s only on the books for one season. However, in the broader context of the offseason’s overall budget, many fans worried that his salary would dissuade ownership from authorizing spending on a potential foundational piece for the future.
The majority of the Yankees’ rumors were dominated by the dance between Bellinger and the front office — Cashman adamant in his desire to keep Bellinger in the Bronx, and Bellinger and Scott Boras holding out for an unattainable jackpot before returning to reality when a seven-year offer failed to materialize. The two sides reunited on a five-year, $162.5 million contract with Bellinger possessing opt-outs after each of the first two seasons. Because of how much money is front-loaded in the terms, Bellinger will be the Yankees’ most expensive player in 2026 and 2027 carrying a luxury tax hit of $44.75 million — almost $5 million more than the AAV of Aaron Judge’s contract and roughly $6 million less than Juan Soto’s AAV with the Mets.
While not an identical roster to 2025, the Yankees’ external additions could still be construed as lateral moves at best. They traded for lefty starter Ryan Weathers from the Marlins, but he’s effectively replacing Schmidt in the rotation as the latter recovers from Tommy John surgery. They lost two of their highest leverage relievers in Williams and Weaver, but filled their vacancies with a Rule 5 dice roll (Winquest) and the worst qualified reliever in baseball in 2025 (no matter how tantalizing the stuff might be) in Angel Chivilli. And of course, true to form, Cashman likened Gerrit Cole’s return from Tommy John rehab to a big-ticket acquisition despite the now-35-year-old starter having pitched just 95 innings since the end of 2023. Cashman also cited the 2025 Trade Deadline additions as 2026 pickups as well, given that the likes of Bednar and Doval will now have full seasons in the Bronx.
Obviously, all of these decisions have to be viewed in the context of the needs of the roster and the players they declined to pursue to upgrade it. Cashman somewhat oddly labeled Kyle Tucker as the backup plan to re-signing Bellinger despite the former being the younger, more superior player and settling for a short-term (albeit a record-high-AAV) deal with the Dodgers. They were vaguely linked to Bo Bichette before he signed his own short-term, high-AAV deal with the Mets, but seemingly felt that the defensives upside and cheaper cost offered by Ryan McMahon and Anthony Volpe justified passing on Bichette’s superior offensive profile.
The same goes on the pitching side. They were never players in the markets for the top-end names like Dylan Cease, Framber Valdez, and Ranger Suárez. They passed on Tatsuya Imai, who joined Astros for a surprisingly cheap three years and $54 million. They had varying levels of interest in trading for Freddy Peralta, MacKenzie Gore, and Edward Cabrera, but opted for the less expensive option in Weathers, despite the expectation that Cole, Schmidt, and Carlos Rodón will miss the start of the season as they rehab from their respective elbow surgeries. For whatever it’s worth, at the end of the day, both FanGraphs and Baseball Prospectus project the Yankees as the 2026 AL East winners, though both also project the Mariners and Dodgers for better records and World Series odds.
So now I would like to turn it over to you. Do you approve of the job Yankees GM Brian Cashman has done this winter in filling out the roster? Additionally, we are asking that you assign a letter grade to the Yankees’ offseason, giving us a slightly more concrete understanding of how the fanbase is feeling heading into spring training. Vote in our poll below: