If there’s one thing Brian Cashman has consistently done well in his tenure as Yankees GM, it’s knowing which prospects to part with in trades. Whether the return ends up being a home run or a total miss, more often than not, the Yankees don’t end up haunted by the names they let go. That track record doesn’t make every deal a winner, but it does mean the long-term damage is often minimal - even when the short-term results sting.
Take Agustin Ramirez, for example. He’s turning heads with his bat, no doubt.
But when the return is someone like Jazz Chisholm, who’s brought serious impact to the Bronx - think 40-40 potential over a full season - it’s hard to second-guess the move. The Yankees gave up a promising hitter, sure, but they got a dynamic playmaker in return.
Which brings us to one of the roughest trades of the last few years - not just for the Yankees, but across the league. The 2022 deadline deal for Frankie Montas was a swing and a miss, and not the kind Yankees fans like.
At the time, Montas had shoulder concerns that dated back to June, but the Yankees either believed he was past it or figured the injury discount was worth the gamble. It wasn’t.
That summer, the Yankees were flying high. The record was elite, the vibes were strong, and the farm system was buzzing with names like Jasson Domínguez, Anthony Volpe, and Ken Waldichuk.
All three were Futures Game selections that July in Los Angeles - a sign of how bright the future looked. But within weeks, the team hit a tailspin, and Waldichuk was on his way to Oakland as part of the Montas package.
Montas’ time in pinstripes was brief and brutal: eight starts, a 6.35 ERA, and zero playoff impact. Waldichuk, meanwhile, never found his footing in Oakland.
He posted a 5.28 ERA across two seasons, underwent Tommy John surgery, and hasn’t pitched in the majors since 2023. On Monday, the A’s designated him for assignment to make room for Jeff McNeil - a move that quietly closed the book on one of the more forgettable trade returns in recent memory.
Waldichuk was considered one of the key pieces in that deal. He had shown flashes in the minors - a lefty with strikeout stuff and some projection - but it never translated at the big-league level.
Even before the surgery, his outings were inconsistent. Afterward, he struggled to regain form.
Now, he's available again, a potential reclamation project for any team willing to take a flier.
So, what does this all mean for Cashman and the Yankees? In a strange twist, the Montas deal - as disastrous as it looked in real time - might not have cost the Yankees much long-term.
Waldichuk didn’t blossom in Oakland, and the rest of the package hasn’t made waves either. That doesn’t excuse the trade, of course.
Montas was acquired to help a team chasing a title, and instead, he became a symbol of a season that fell apart.
The A’s didn’t win the trade either, but at least they offloaded a damaged asset. The Yankees, on the other hand, got burned at the worst possible time. The rotation needed a boost, and instead, they got a pitcher who never found his footing in New York.
Now, with Waldichuk back on the market, there’s a bit of irony in play. A reunion wouldn’t move the needle much - not unless he can rediscover the form that once made him a top-10 Yankees prospect. But the fact that he’s available again underscores just how little long-term value changed hands in that deal.
In the end, the Montas trade stands as a cautionary tale. Not every deadline move pays off, and sometimes, even when the cost seems manageable, the timing and circumstances can make a bad trade feel even worse.
For Cashman, the silver lining is that the prospects he gave up haven’t come back to haunt him. But that doesn’t mean the Yankees - or their fans - have forgotten how much that deal took the wind out of a promising season.