​NEW YORK — We’ve reached the All-Star break, and outside of the Dodgers clinching the National League West, there aren’t clear answers about the second half of the season. Instead, there are a lot of lingering questions. Let’s begin with the Yankees. If Ryan McMahon truly did give New York a spark with that grueling 12-pitch at-bat against the Rays’ Rays ace Drew Rasmussen last Thursday, what can Brian Cashman do to adequately fix the roster for a deep postseason run? Answer: it hinges on Aaron Judge’s broken rib imaging. “I don’t think it’s coming back clean,” Cashman said of the imaging scheduled for the break. “I think we’re anticipating that it’s showing the healing process.”
Still, even in the best-case scenario, Judge would be back in the field only in mid-to-late August, and there remains substantial pessimism about him returning at all this season. Giancarlo Stanton sits in a similar limbo. If there’s no certainty that Judge will be back, then the Yankees must face the reality that a World Series run this year is unlikely, and there might be little point in pursuing aggressive moves at the trade deadline. But even if imaging offers a glimmer of hope, Cashman must thread a needle to address the team’s many needs—a right-handed hitting catcher, another back-end reliever, a back-of-the-rotation starter, and a contact hitting bat—without sacrificing too much prospect capital on what would likely be two-month rentals.
Before their 12-4 burst against the Rays on Thursday, which salvaged a 2-2 split in the series in Tampa, the Yankees were 5-15 since June 18, the worst record in baseball over that stretch. They had scored just 56 runs in that span, also the major-league low. Fans were again calling for Cashman and Aaron Boone to be replaced. While that ire is understandable, I don’t agree that Cashman has performed poorly in assembling the roster, especially given that he essentially brought back the same core that won 94 games last season. What more could supporters have asked for?
Where I place accountability is Cashman’s seemingly blind loyalty to his top draft picks—particularly Anthony Volpe and Austin Wells, two notable liabilities in the immediate term. In Wells’s case, finding a suitable right-handed catcher on the trade market now could prove difficult, especially if the Twins decide to chase a wild-card spot and keep Ryan Jeffers. And I wonder if Cashman will ever concede that the Yankees might be a better team with Jose Caballero, who proved to be his strongest acquisition at last year’s trade deadline, at shortstop.
As for potential targets to fill the team’s needs, make no mistake: the Yankees are not going to be pursuing Tarik Skubal. Whether he’s even available remains uncertain, given the Tigers’ willingness to listen and the broader market dynamics for pitchers, but New York’s scout for a mid-rotation arm is not likely to tilt in Skubal’s direction. In short, the Yankees face a delicate balancing act: fix the roster enough to contend in a potential postseason push without compromising the long-term plan by overleveraging prospects. The next steps will reveal whether Cashman can reconcile those competing imperatives and plot a course through the uncertain late-summer stretch.