The Yankees went into the 2026 MLB trade deadline needing bullpen help, and Brian Cashman came away having done the opposite of solving the problem. After subtracting from an already thin relief mix in the Luis Garcia Jr. trade, the club still failed to add the kind of arms that could steady the late innings. For Joel Sherman, that was enough to go off.
In a video posted to Twitter/X by the New York Post, Sherman unloaded on the Yankees’ decision-making and made it clear he does not trust the current plan.
"I am blown away! I am blown away that [the Yankees] don't have at least one more capable relief pitcher on their staff today.
I think they [needed] two more capable, throw 40 innings the rest of the year, you believe in it [relievers]. Because I just don't believe everything in this game of Jenga is going is going to go right," Sherman raged.
He kept going, and the bigger point was even sharper: the Yankees’ pitching situation is too fragile to assume everything breaks the right way over the final stretch.
"Forget about Judge, Bellinger, and Stanton for a second. I don't think with their pitching staff, how many different things have to go right over the next eight to twelve weeks if you get to the end of October for this to work," he continued.
That “game of Jenga” line is really the heart of the criticism. The Yankees appear to be leaning on a patchwork solution built around internal options and role changes.
Clarke Schmidt is working back from Tommy John surgery and is being viewed as a possible bullpen answer. Another path is moving either Will Warren or Ryan Weathers to relief once Carlos Rodón is activated from his upcoming rehab assignment.
But that setup comes with obvious danger. Any setback in the rehab process could blow the whole thing up.
An injury in the rotation would create another hole the club can’t afford. And asking pitchers to change roles in the middle of the season, right when the pressure spikes, is a risky way to build a bullpen.
Sherman has gone at Cashman before, too, and the history between them isn’t exactly quiet. In November of 2023, Sherman pressed the Yankees on Anthony Volpe and player development, and Cashman snapped back with a defense of the organization’s process.
“I think our player development system does a great job. You are questioning whether it does.
The proof will be in the pudding…. When Volpe crushes it offensively for us, you’ll say, ‘Hey, I guess your development program did a good job.’
It’s pretty basic,” Cashman fumed.
Now, nearly three years later, Volpe is sitting on a .660 career OPS and has been demoted to Scranton in favor of George Lombard Jr. That prediction did not age well.
Cashman may not see it that way, but there were relievers available at prices the Yankees could have handled. Instead, the club is betting on internal reinforcements and hoping Paul Blackburn and Angel Chivilli, once he’s able to resurface, keep stepping up. It’s a lot to ask, and Sherman’s read on the situation is the one that sounds a lot more convincing.
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