The 2026 Yankees won 93 games in a year in which superstar Aaron Judge played just 66 games. That’s not a bad total, but it feels like it could, and should, have been more. General manager and Senior VP Brian Cashman routinely builds contending teams, and he should get credit for that, but he and his staff should be aiming higher and doing more to bring the title back to the Bronx.
A Wild Card Series win against the Boston Red Sox was a nice way to start the postseason, but the sweep at the hands
of the Tampa Bay Rays exposed many harsh realities that are directly tied to Cashman and his decisions.
For the Yankees, 93 wins is not enough. They need to be the best team in the division, because that would bring them additional benefits in postseason play, such as home-field advantage and a ticket straight to the AL Division Series. Everybody in the organization is responsible for how the season plays out, but the spotlight will always point to the head of baseball operations.
Offseason moves and decisions
Cashman didn’t have a particularly bad offseason, but there were some notable holes when the season started. He didn’t find proper replacements for the rehabbing Anthony Volpe and the underwhelming Ryan McMahon: the former ended up being demoted in early August when the organization promoted George Lombard Jr., and the latter posted a 78 wRC+ and just 0.5 fWAR in 124 games. Volpe eventually returned and played an important role in the stretch run and during the postseason.
Extending Trent Grisham a qualifying offer was seen as a moderate risk when it happened, but it was a reasonable one since the outfielder had hit a career-high 34 homers in 2025. The outfielder declined this year, particularly on defense, but at least it wasn’t a long-term commitment.
The trade for Ryan Weathers was universally acclaimed, and it was a good piece of business on Cashman’s part. He ended up posting career-bests in ERA (3.60), fWAR (2.5), and innings pitched (137.1). The executive also brought back Paul Blackburn, Ryan Yarbrough, Amed Rosario, Paul Goldschmidt, and Cody Bellinger.
Some of them were nice additions, particularly the 2019 NL MVP, but Cashman left the roster exposed to injuries and underperformance in many spots, and that’s on him, too. The bullpen was a bit thin, as some of his past trade experiments, such as Jake Bird, Ángel Chivilli, and Camilo Doval, just didn’t work. The same can be said about Rule 5 pick Cade Winquest. We are more than willing to give Cashman a pass in the bullpen, since the unit finished with the second-best ERA in MLB, though.
Trade Deadline activity (or lack thereof)
The Bombers entered the deadline with a few notable needs, which Cashman was very much aware of. They could have used a catcher given Austin Wells’ season-long slump up to that date, a reliever or two, a starter, and a right-handed outfielder.
They flirted with several backstops, but ended up empty-handed on that front to the frustration of fans. They did bring in Luis García Jr., who had been enjoying an amazing year in Washington with 23 homers and a 133 wRC+.
Heliot Ramos’ arrival was met with mixed reviews, and he posted a disappointing 93 wRC+ in pinstripes. He did have a 184 wRC+ vs. lefties during his time in the Bronx, which was one of the main reasons behind his acquisition. Giving up left-handed pitching prospect Henry Lalane to get him hurt, though. Speaking of…
Prospects and young core
Yes, you could say that the Yankees’ deadline was a disappointment, although some might disagree. However, they managed to keep most of their top prospects, including Lombard, Dax Kilby, Carlos Lagrange, Elmer Rodríguez, and Ben Hess. The promising Lalane was the lone exception.
They represent, together with Cam Schlittler, Ben Rice, Spencer Jones, Weathers, and Will Warren, the next wave of young talent that will, theoretically at least, keep the team highly competitive for the next 3-7 years. Keeping them all, particularly Lombard when half the league was asking for him in trade conversations, was a win for Cashman.
The rest of the farm, however, needs work. A lot of work. The Yankees will need to draft well and be active in the international market in the next couple of years to revamp their depleted system. At least Cashman took a step towards solving the situation, dismissing longtime international scouting director Donny Rowland and replacing him with Mario Garza in January.
Player development wins and losses
As every general manager, Cashman had some player development wins and losses when looking at the final picture of the 2026 campaign. He and his staff managed to turn Blackburn into a very useful reliever with his 1.59 ERA in 85 innings, and he got a nice season from Weathers, too.
Schlittler took a step forward into stardom, and Brent Headrick and Warren also improved in 2026. On the other hand, they couldn’t fix Doval, Luis Gil, McMahon, or Volpe, and Jasson Domínguez remains a fringe player. Grisham and Wells were also subpar for their standard.
The offense, generally speaking, had a mediocre year with a 101 wRC+ that ranked 14th in MLB. Yes, injuries to Judge, Giancarlo Stanton, and other key hitters certainly hurt, but the feeling is that Cashman could have done better, or more.
Bottom line
We have said it multiple times in this space: the Yankees need new voices. They need to listen to more prepared people. They can’t keep doing the same things in personnel decisions, player analysis, research and development, and scouting and expect different results. Unless the ownership decides to part ways with their longtime executive, it will be on Cashman to push that change within the organization: does he have that in him, though? It’s at least a fair question.
