Will the Yankees need another midseason makeover?

The modern Yankees are known at this point for their midseason slumps, but they also deserve credit for the late-season surges that those slumps necessitate. Last year, after going 25-27 through June and July, the club closed the season on an MLB-best 30-11 run.

That run was in part thanks to a midseason makeover that was forced by the team’s shoddy midsummer play. With the club slipping to five games back in the AL East, Brian Cashman imported seven players at the trade deadline, and though not all of them excelled in pinstripes, the stronger pickups, David Bednar, José Caballero, and Ryan McMahon, combined for over 3 rWAR, crucial contributions in a division race that came down to the final day.

As the Yankees limped through July, it was clear they needed major reinforcements, and the front office responded. It’s early days in 2026, but the Yankees have already shown their trademark inconsistency, and they again appear to have some major holes on the roster. So, do you think they will need another midseason makeover this year?

With such glaring holes in their infield at the moment, the answer to this question may seem like an obvious “Yes” to some, but let’s at least hear the optimistic case. For one, among the primary issues the Yankees had to address at last trade deadline was how left-handed heavy their lineup was, leading to the acquisitions of Amed Rosario, Caballero, and Austin Slater. In theory, this version of the team doesn’t need the same kind of augmentation, with a bench full of right-handed bats capable of stepping in against lefties (in practice, of course, the lineup has struggled thus far against southpaws).

Moreover, pitching is where so many contending teams look to add midseason, and the Yankees are loaded with it. Their starting rotation has paced the league, with Carlos Rodón, Gerrit Cole, and potentially Clarke Schmidt still on the way. Injuries very well may eat into the club’s depth and force them to add more arms, but should Cole and Rodón return healthy, the Yankees may be close to set on pitching. At full health, they’d have more talented arms than slots in the rotation, allowing them to address any bullpen weaknesses by shifting arms to relief, and that’s before even mentioning talented prospects like Carlos Lagrange and Elmer Rodríguez

That’s the optimistic case, but the more pessimistic case isn’t too hard to spell out. Ryan McMahon and Caballero have barely been playable as a starting left-side this year, and the bullpen cries out for reinforcements. Perhaps Anthony Volpe comes back healthy and productive, and maybe the Yankees’ excess of starting pitching helps them address their bullpen needs. Or, perhaps the Yankees need to find two starting caliber infielders at the deadline, and multiple capable bullpen arms, much like they did last year.

What do you think? Will another midseason roster makeover be necessary? Or will something more akin to the 2024 deadline, when the Yankees only made a couple of additions, be the path the club takes?

On the site today, you can get caught up on Wednesday night’s AL action with Kevin’s Rivalry Roundup, and read up on a Hall of Famer you probably didn’t know play for the Yankees in Matt’s profile of Paul Waner. Also, Peter’s sequence of the week highlights some quality work from Will Warren, and Andrés reviews another shaky from Luis Gil.