Any New York Yankees fan hoping GM Brian Cashman would swoop in and significantly bolster the team's roster ahead of the MLB trade deadline was left sorely disappointed. The additions of first baseman Luis Garcia and outfielder Heliot Ramos are hardly the sort of moves that are going to help the Yankees schedule a parade down the Canyon of Heroes.
Instead of taking a big swing, Cashman chose to stay patient and try to build Aaron Boone's roster for the long haul. At some point, though, he'll need to go all-in if he wants to finally achieve some measure of glory for baseball's most storied franchise.
The most pressing question about Cashman's tenure in the Bronx is which mistakes have really cost the franchise. The following five errors represent Cashman's biggest misses of recent vintage, ones that have left his team trending in the wrong direction as October looms.
The Yankees ignored their weakness at third base
It might surprise quite a few Yankees fans to learn that catcher Austin Wells does not have the lowest WAR in Boone's preferred starting lineup. That honor goes to third baseman Ryan McMahon, who sports a WAR of just 0.2 on the season.
The former All-Star used to prop his value up with borderline elite defense at the hot corner, but he's slipped to the point that he's actually a slight negative with his glove. That makes his trouble making contact at the plate even more of an issue for the Yankees on a nightly basis.
Giving McMahon a chance to play his way into form this year was a reasonable gamble by Cashman, but he should have made a move at the deadline to correct his mistake. McMahon and Amed Rosario are not a good enough platoon for a team that fancies themselves as World Series contenders.
Brian Cashman should not have led the Red Sox outbid the Yankees for Adley Rutschman
Plenty of people criticized the Red Sox for overpaying for Adley Rutschman at the deadline, but the Yankees should have been willing to beat out their arch rivals for the All-Star catcher. Instead, Cashman opted to continue to pin his hopes on Wells to rebound from his nightmare start to the 2026 campaign.
New York also could have solved their issues behind the plate by landing someone like Hunter Goodman or Ryan Jeffers. The real sin here is doing nothing to boost production at the catcher spot. Wells has shown slight glimpses of recovery lately, but the chances of him being anything more than an average starter down the stretch are slim.
The Yankees would have needed to pay a steep prospect price to land Rutschman, but doing so would have turn their biggest weakness into a strength. Instead, they'll be forced to watch him boost Boston's win total for the foreseeable future.
The Yankees should have bolstered their bullpen at the trade deadline
Cashman deserves credit for offloading some underperforming relievers at the deadline, but his inability to add any reinforcements defies all logic. At the very least, a modest addition could have helped slot the entire group back into suitable roles as October nears.
The logic from Cashman is that internal reinforcements will do the job. Clarke Schmidt is on pace to return relatively soon and will need to pitch out of the bullpen as he builds his arm strength back up after Tommy John surgery. The impending return of Carlos Rodon to the rotation should allow either Will Warren or Ryan Weathers to head to the bullpen as well.
The problem with that logic is that no one can foresee how any part of that trio will adjust to life as a reliever in the midst of a pennant race. Adding just one proven, competent arm could have boosted the Yankees bullpen in a major way. Cashman stood still and his team will pay the price in the postseason.
Hanging on to Jasson Dominguez this long will further crater his trade value
Jasson Dominguez is a victim of the ridiculous hype that accompanied his journey to the Majors. There was a time when he could have gotten the Yankees a fair amount in a trade. That opportunity passed at this year's deadline.
Instead, New York sent Dominguez back down to Triple-A to work on his craft despite the litany of injuries the team faces in the outfield. Spencer Jones won the battle to stay in the Bronx despite his inexperience and issues making consistent contact.
Now it's hard to see where Dominguez will fit into the Yankees in the near or medium future. Cashman will likely be forced to accept a cut-rate deal in the offseason that helps clear up his 40-man roster. That's a disappointing end for a player who was once regarded as a top prospect and could have been used as that kind of trade chip.
Add us as a preferred source on Google