Yankees can win trade deadline if Aaron Boone doesn't get in the way

With the All-Star break come and gone, it's time for every would-be contender to turn their full attention to the upcoming trade deadline — their last, best chance to patch holes and load up for the stretch run. For the New York Yankees, pretty much all of the speculation in recent weeks has focused on the team's search for a third baseman; Jazz Chisholm Jr. has finally been put back at his rightful place at second base (much to the chagrin of DJ LeMahieu), but that has left a gaping hole at the hot corner, where Oswald Peraza has been one of the worst hitters in the sport so far this season.

But for as badly as the team needs an upgrade there, it's far from the only need that needs to be addressed. New York's rotation has been battered and bruised over the last few months, from Gerrit Cole and Clarke Schmidt needing Tommy John surgery to Luis Gil going down with a balky shoulder early in the spring. The Yankees have weathered the storm well enough, with Max Fried and Carlos Rodon anchoring things at the top and top prospects like Will Warren and Cam Schlittler maturing more quickly than expected. Still, you can never have enough pitching, and Brian Cashman figures to try and add at least one more arm between now and July 31.

That raises some thorny questions, though. If Cashman does add another starter, who would be at risk of getting bumped? Gil has already begun a rehab assignment, and he looks as good as he did during his breakout rookie campaign in 2024.

Gil figures to be back at some point in August, and that could create something of a logjam in the rotation — one that manager Aaron Boone might not be the right man to solve.

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Projected Yankees rotation once Luis Gil returns

Here's how things look as New York gets set to return to action this weekend against the Atlanta Braves.

It's a testament to the depth Cashman has developed that New York still has what shapes up to be a functional six-man group despite losing Cole and Schmidt to serious injury. But even though Gil is nearly back, and even though Warren and Schlittler have looked the part of back-end starters at the very least, the Yankees should be motivated to add at least one more arm at the deadline.

For starters, there's no guarantee that Gil will be able to stay healthy, or that he'll hit the ground running after missing half the year. And while Warren and Schlittler have flashed serious promise, they're both rookies, and they're both about to enter uncharted territory. Stroman has done a fine job of eating some innings when called upon, but he's hardly a guy you want to rely on to win meaningful starts in September.

The Yankees don't need to spend through the nose for Joe Ryan or Sandy Alcantara, but they do need some depth, a little insurance against regression or further injury from some of the riskier guys behind Fried and Rodon. If Cashman manages to find that depth, though, suddenly the pressure will be on Boone to help navigate a tricky situation. And he's hardly earned the benefit of the doubt on that front.

Yankees' rotation upgrade will require Aaron Boone to make some tough choices

Boone can sometimes get a bit too harsh of a rap among Yankees fans; he's not the one who ignored the team's questionable infield situation over the winter, and he's not the one causing pitchers to get hurt or the bullpen to turn into a pumpkin overnight. But even if you want to be charitable, it's fair to say that Boone's management of his clubhouse and the various personalities in it has left something to be desired of late.

His stubborn loyalty and faith in "his guys" (scare quotes very much intended) earn him the trust of his players, but can also lead to blind spots; just look at how he's handled both LeMahieu and the struggling Anthony Volpe. The stretch run is no place to play sentimental favorites, especially given how much the Yankees have riding on this season and every season in which Aaron Judge is still in his prime and performing at an historic level.

That will be especially true if Cashman gets this team the pitching help it needs at the deadline, and New York is forced to decide which starting five it wants to roll with for the last two months of the regular season. There's a path here for New York to really take off: If Gil comes back looking like himself and the Yankees pick up, say, a fifth starter type like Charlie Morton, they could pivot Warren or Schlittler to a role as a multi-inning weapon out of the bullpen a la Michael King. Two birds would be killed with one stone, and suddenly this pitching staff would look pretty fearsome.

Of course, that would require Boone to do the hard thing and deliver some bad news, all while making sure it doesn't become an undue distraction to the rest of the team. Maybe he can come through; he did, after all, finally jettison LeMahieu. But Yankees fans have reason to be skeptical.