One of Yankees' most inexplicable trade deadline acquisitions signs with Dodgers

Back in 2023, the New York Yankees were up against it. Aaron Judge injured his toe by running into the right field wall at Dodger Stadium and crashing into the concrete base. After he went down, the Yankees started to slide, going 11-12 in June and 10-15 in July.

It was clear they needed reinforcements at the trade deadline if they wanted to remain afloat as Judge was on the mend. The fanbase was clamoring for any change that could've helped the roster stay in the playoff picture, but their wishes were not granted. Brian Cashman went out and acquired reliever Keynan Middleton from the White Sox and ... that was it.

One move. For a middle reliever. As the team was in a tailspin without their best player. In hindsight, it wasn't the worst decision in the world because not a lot of top talent changed hands at the 2023 deadline. Not only that, but this ended up being the worst Yankees team in 30 years (they finished 82-80 and missed the playoffs).

But, man, at the time, when it was Middleton and nothing else, fans lost their mind. The move was nothing more than a waving of the white flag alongside a false endorsement of the rest of the players tasked with shouldering the load with Judge on the shelf.

Middleton didn't return to the Yankees after his two-month stint and then suffered a flexor strain that sidelined him for 2024 and most of 2025. He hasn't pitched in MLB since those 12 games with the Yankees (he missed pretty much all of September in 2023 with a shoulder issue).

Former Yankees reliever Devin Williams signs with Dodgers in free agency

Now, the right-hander is back on the mend after signing a minor-league contract with the Los Angeles Dodgers over the weekend. Middleton's career began in Anaheim, after he was drafted by the Angels in the third round back in 2013, and he's from Oregon, so a return to the West Coast was likely preferable.

Should he revive himself in LA, it'll be a sore subject for Yankees fans, whose ire was fully directed at Brian Cashman — not Middleton — regarding this move. The transaction fell right in line with the narrative that the trade deadline has rarely been kind to New York throughout the Aaron Judge era.

Maybe Cashman's 2025 moves will translate well in 2026 and we can forget about all of this. We're sick of picking at old wounds every time we see a random name pop up regarding an inconsequential signing.