Zac Gallen and Jacob deGrom top the list of starting pitchers that could be moved at the trade deadline. While Luis Gil continues his recovery with the Yankees, he is still faces a long road back to the major leagues. Cashman has a history of making big moves halfway through the season. After falling short in the World Series in 2024, New York needs to make the most of their success.
Third base might be the priority at the deadline, but starting pitchers should also be on the Yankees’ radar. Right now, Max Fried and Carlos Rodon are the only two playoff-ready pitchers at Aaron Boone’s disposal. New York’s manager is one of the best in Major League Baseball, but a lack of top-level pitching is tough to overcome in the postseason.
When it comes to trade assets, the Yankees have as much as any team in the league. No matter who is actually available on the market, New York can outbid most other teams in MLB. It comes down to how badly they want to make a deal and how much they trust their roster. Gil could be a saving grace once he returns. Will Warren has been shaky since the Yankees called him up.
Cashman has some tough decisions to make with the deadline two weeks away. After New York designated DJ LeMahieu for assignment, fans were treated to a bit of the chaos that could define the Yankees’ season.
Without Schmidt, the Yankees lack a reliable third option

With Schmidt out for the rest of the season, Cole’s injury hurts even more. When they are at full health, the Yankees’ pitching staff is as formidable as anyone’s. However, a completely healthy roster is a pipe dream in professional sports. The best that teams can hope for is that the majority of their roster can stay intact. In New York, that has not been the case this season.
Boone has made a name for himself by working around injuries to find success. However, the cards are stacked against him ahead of the second half of the season. Schmidt, Cole, and Gil would have completed their playoff rotation. Instead the pressure to perform shifts to Marcus Stroman, Warren, and Cam Shlittler.
Stroman started the season threatening not to play. According to reports, the New York pitcher wanted a spot in Boone’s rotation. For better or worse, his wish has come true. If the Yankees want a chance to re-take the lead in the American League East, Stroman needs to be dominant. If not, Boone’s work is cut out for him as he searches for any kind of production.
Who could the Yankees bring in to prop up their pitching?

deGrom will be the star of the deadline when it comes to starting pitchers. Because of that, teams will line up to overpay for the veteran. While they do that, pitchers like Gallen and Sandy Alcantara could fly under the radar. The Yankees have been attached to Gallen for months as the Arizona Diamondbacks continue to struggle in the National League West.
His expiring deal makes him a great target for Cashman to prioritize before the deadline. At his age, he would be a great long-term fit alongside Cole and the rest of Boone’s starters. He is in the middle of a down season, but the starter was the leader of a rotation that made it to the World Series in 2023. He is a perfect, buy-low option for New York to pounce on.
Gallen’s numbers have been underwhelming to say the least. His 7-10 record is his worst in four years. A 5.40 ERA is enough to scare away most other suitors. However, the Yankees could view his 1.37 WHIP as a good reason to give him a chance in a new home. If a change of scenery is all he needs to return to his former glory, he could be a steal for Cashman.
Regardless of what happens at the deadline, New York has their work cut out for them this season. The Yankees can’t waste another Aaron Judge MVP caliber season. However, their current starting rotation could end up holding them back when it matters most. It is on Cashman and the front office to find a starter who can come in and help the team reach their lofty goals.