The Yankees have not been able to get the job done in the playoffs for years. Their last World Series win came in 2009, and they have reached the Fall Classic only once since. This year seemed different, with the powerhouse that was the starting rotation, sporting the three-headed monster of presumptive Cy Young Award winner Cam Schlittler, former winner Gerrit Cole, and Max Fried (which does him no justice leaving his description at just his name).
However, the Yankees were sent back to the drawing board into the smoky abyss that is the 2026-2027 offseason, given the CBA debates and potential lockout to ensue. With some of their core folks getting older, they will have to be creative to maximize a closing window.
Here are 3 free agents (and a bonus cluster of players) the Yankees should make priorities this offseason:
1. Teruaki Sato
New York hasn't gotten what it wanted out of Ryan McMahon. Known more for his defense than his bat, McMahon was acquired with hopes of keeping his power from Colorado via the short porch in Yankee Stadium while maintaining his slick defensive prowess. Unfortunately, he has taken a step back from his high defensive standard since putting on the pinstripes, and popping just 15 homers in 178 games with New York - not enough for a $16 million man.
Teruaki Sato would be the first time the Yankees tap into the NPB since Masahiro Tanaka, and could provide a much-needed spark to the offense. Last year, he hit over .300 with 39 homers, and 40 homers the year before. He is also a lefty bat, which will likely play well at the Stadium. The Yankees could shake things up, but would then have to decide what to do with the incumbent McMahon.
2. Adrian Morejon
The Padres reliever has been dynamite for the past three years, solidifying himself as one of the league’s premier relief arms. Earning his first All-Star nod in 2025, he posted a career-best 2.08 ERA, striking out 70 across 73.2 IP. In 2026, he improved that ratio, striking out 107 in 86 IP.
With Tim Hill and Ryan Yarbrough hitting the market, the Yankees could be looking to stock up on some lefties - especially if Ryan Weathers is kept in the rotation in 2027. Morejon would provide some funk and some punchouts to a bullpen that had fans in shambles in the first half, save David Bednar and Paul Blackburn.
3. Tyler Stephenson
The Yankees clearly believe in Austin Wells, and Wells showed in the second half that he still had offensive production left after a horrid first half. After Brian Cashman balked on both Hunter Goodman and Ryan Jeffers in the trade, the Yankees may be looking to give Aaron Boone at least a platoon option behind the dish. Stephenson could be the option, and at a cheaper price point.
The backstop hit .241 with 15 homers and a .727 OPS last season across 130 games, but has consistently had his OPS sit in the mid-.700s across his young career. His righty bat would provide Boone lineup flexibility every day, and his defense is nothing to shy about, as he threw out 22 runners in 2026.
Bonus: Retention
The Yankees need to retain both Paul Blackburn and David Bednar for the offseason to even be remotely successful. The two pulled the Bombers through the dog days of summer when no one else could, and were two go-to arms for Aaron Boone in high-leverage moments. Bednar has been a rock since coming over to New York, and Blackburn (another Matt Blake masterclass) posted the best ERA of his career by far at 1.59.
If the Yankees lose the biggest pieces of their bullpen, they will have to do even more to fix what wasn’t necessarily a strength in 2026.