The New York Yankees lost again on Monday, giving them 24 in their last 39 games. Their 57-49 record is still good for sole possession of the top Wild Card spot in a weak American League, but they're now 5.5 games back of the first-place Toronto Blue Jays after spending much of the first three months of the year in first place. The Yankees' struggles, along with the recent injury to Aaron Judge, have fans outraged and have put GM Brian Cashman in a bit of a tricky situation.
On one hand, these are the New York Yankees we're talking about here. The expectation every year is to compete for World Series championships, and for the first couple of months, it looked as if the Yankees had a roster capable of getting back to the Fall Classic. On the other hand, the last two months have been telling for this team, and the holes on this roster are prevalent. The Yankees can still get back to the World Series, but major deadline moves would have to be made to start that discussion.
The fact that an argument can be made for buying and selling has made Cashman's job a tough one. With that being said, it sounds as if Cashman won't do his deadline job well, based on what SNY's Andy Martino reported recently.
"But Monday’s 4-2 loss to Tampa Bay did nothing to restore the front office’s faith in the team. It was further reinforcement of their likely approach, on Saturday, to be what you might call 'soft buyers,' making moves that improve the current roster without risking the future," Martino wrote.
Soft buyers? What're we doing here?
For more news and rumors, check out MLB Insider Robert Murray’s work on The Baseball Insiders podcast, subscribe to The Moonshot, our weekly MLB newsletter, and join the Discord to get the inside scoop during the MLB season.
Brian Cashman must pick a firm direction at the trade deadline
The Yankees aren't in a position where Cashman feels comfortable going all-in at the trade deadline by moving some of the organization's top prospects, but with the team sitting in a postseason spot, Cashman doesn't feel like selling either. Thus, we have the Yankees potentially sitting in the middle, the worst place to be.
Let me be clear: I understand why Cashman isn't fully bought into this team. The injury concerns are real, especially with Judge currently out, the struggles over the last two months have been prevalent, and it'd take a lot to get this team back in the true World Series conversation. With that in mind, displaying an unwillingness to trade high-end prospects like George Lombard Jr., Spencer Jones and Cam Schlittler makes sense.
However, if the Yankees won't entertain trading from that trio, or even guys like Carlos Lagrange or Rafael Flores, they should be sellers. No, I don't mean trading Aaron Judge, but veterans on expiring contracts like Cody Bellinger, Paul Goldschmidt, Trent Grisham, Luke Weaver and Devin Williams should be on the block.
The Yankees shouldn't trade their expiring contracts just to trade them, knowing they're in a playoff spot. But if they don't plan on meaningfully adding to their team, they should be open to adding players who can help them win in 2026. Guys like Bellinger and Williams can net New York outstanding returns, especially if the Yankees are willing to pay down their salaries.
The one thing Cashman cannot do is what he might be planning on doing: nothing of importance. Standing pat wouldn't help the Yankees get any better, and wouldn't help them in 2026 either. Whether he decides to clearly buy or clearly sell, Cashman must pick a direction by Thursday's deadline, and not commit one of the period's cardinal sins.