Brian Cashman is staying put.
The Yankees general manager said this morning that he has agreed to a new contract, even if the final paperwork still isn’t official. With manager Aaron Boone also set to return next season, New York is bringing back the same two men guiding the club from the dugout and the front office.
Cashman has now been the Yankees’ GM since 1998, making him the longest-tenured front office leader in the sport. His previous deal covered 2023 through this season, so an extension had been expected, especially given his long run in the organization and the club’s history with contract talks. The timing makes sense too: New York has typically not shown much interest in extensions until a contract runs its course.
The Yankees finished with the top AL Wild Card spot, rolled past Boston in the Wild Card round, and then ran into a wall against the Rays in the ALDS. Tampa Bay eventually won the American League pennant, but New York’s exit came with a familiar sting. It was the second straight season the Yankees were eliminated in the divisional round, and both times they lost to the AL’s World Series representative.
Owner Hal Steinbrenner did not point the finger at Boone or Cashman after another short postseason run. He instead blamed the offense.
“ I don’t think you can pin the season and the unacceptable end to it on Aaron [Boone],” Steinbrenner told reporters (h/t Greg Joyce of the New York Post). “ I don’t think you can pin it on [Brian Cashman].”
The bats were loud against Boston, with the Yankees scoring nine runs in each of the two Wild Card games. That momentum disappeared against Tampa Bay.
New York managed only five runs across the three-game series, including a Game 1 shutout in which Drew Rasmussen took a no-hitter into the eighth inning. Game 2 was just as messy, with the Yankees committing more errors, four, than they had hits, three.
The postseason issues were only part of the problem. Once Aaron Judge went down at the end of May, the Yankees’ offense cratered for a long stretch.
Over the next three months, they ranked 25th in scoring and were tied with the Angels for the worst wRC+ in baseball from June through August. Judge’s return didn’t last long, though the club did climb back to middle-of-the-pack offensively in September.
Now Cashman heads into an offseason with some real decisions waiting. David Bednar and Jazz Chisholm Jr. are both free agents, and both could be candidates for qualifying offers - even if that approach burned the Yankees with Trent Grisham this year.
Cashman may also need to find ways to shore up an aging rotation that took a beating from injuries. Gerrit Cole, Carlos Rodon, and Max Fried are all in their mid-30s, while Clarke Schmidt is heading into his age-31 season.
There’s also the matter of the lineup puzzle. Judge’s calf injury kept him out of the postseason after he pushed to get back, and Giancarlo Stanton missed almost the entire regular season because of lower leg issues before appearing in the playoffs. If both are healthy, the Yankees will have to sort out the playing-time squeeze with Ben Rice also in the mix for first base and designated hitter at-bats.
In Other News...
Yankees Just Lost A Key Coach In A Troubling Development Blow
The Yankees are losing one of the more quietly important figures in their development pipeline, as the Astros have hired Spencer Medick away from Triple-A to become their new director of pitching. Medick had been in the organization since 2022 and spent time working with Cam Schlittler during the right-handers rise through the minors, a stretch that helped shape one of the most encouraging young pitching stories in the system.
Schlittlers 2026 season only sharpened the interest around that work, finishing with a 1.95 ERA, the lowest qualifying mark for the Yankees since 1978. So while the move is being made at the staff level rather than on the major league roster, it still lands as a meaningful development loss for a club that has leaned heavily on continuity in its pitching instruction. [Read more 🡒]
Aaron Boone Just Made Jazz Chisholms Yankees Future Feel Clear
Jazz Chisholm Jr.s first full run in pinstripes never quite settled into the kind of season the Yankees were hoping for, and it ended with more questions than answers. His uneven 2026 performance was already under the microscope before a costly throwing error in the ALDS only added to the scrutiny, making the fall feel even steeper for a player brought in to bring energy and production.
Then Aaron Boone said the quiet part out loud. The Yankees manager made it clear that Chisholms approach has rubbed him the wrong way, pointing specifically to the kind of behavior that can grate inside a clubhouse, and the comments only sharpened the sense that Chisholm may not be part of the teams long-term plans. For a player whose talent still makes him intriguing, the issue now is whether the Yankees see enough fit beyond the flashes to keep the relationship going. [Read more 🡒]
Yankees Fifth Starter Battle Comes Down To Upside Or Reliability
The Yankees have plenty to like at the top of their rotation, with recent All-Stars like Gerrit Cole, Carlos Rodn and Max Fried headlining a group that also includes Cam Schlittler. The question now is less about star power than about how to round out the back end, where the fifth-starter spot has turned into a familiar kind of camp debate: do the Yankees lean into upside, or do they choose the arm they trust most to take the ball and keep them in games?
Ryan Weathers looked like a real candidate after a solid 2026 season, but the forearm injury he suffered late in the year complicates his case. Will Warren, meanwhile, brings the kind of durability teams value in April and beyond, having topped 150 innings in each of the past two seasons, even if his command can wander at times. For a club built to expect excellence from the front of the rotation, the final choice may come down to whether it wants the ceiling of a comeback candidate or the steadier profile of a workhorse who does not always have perfect feel. [Read more 🡒]