Brian Cashman was busy again at the 2025 trade deadline, orchestrating several deals that helped the New York Yankees win 30 of their final 44 games and secure a playoff spot for the eighth time in nine seasons. However, some deals were certainly more significant than others. This is how I would, retrospectively, grade each major deal made by the Yankees at last season’s trade deadline.
Yankees Acquire Caballero From Rays
Yankees Receive: Shortstop Jose Caballero
Rays Receive: Outfield Prospect Everson Pereira
Given Anthony Volpe’s subpar production, a move for a shortstop seemed inevitable as the 2025 trade deadline approached. That move came in the form of acquiring the speedy Jose Cabellero from the Tampa Bay Rays in exchange for outfield prospect Everson Pereira.
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In 40 regular-season games for the Yankees, Caballero hit .266 and posted an OPS of .828. He also stole 15 bases to complement the above-average defense he played at shortstop. Caballero even showcased his power, hitting three home runs with the Yankees after hitting two in 86 games for the Rays. He hardly saw the field in the postseason as Volpe held down the position, but Caballero was a key contributor down the stretch for the Yankees, nonetheless.
With Volpe set to miss the first few weeks of the 2026 season, Caballero is primed to be the Yankees’ starting shortstop to begin the year. However, if Caballero performs close to how he did late in 2025, Volpe will be all but forced to earn back his starting spot in the infield.
Grade: A-
Yankees Swap Pitching Prospects for McMahon
Yankees Receive: Third Baseman Ryan McMahon
Rockies Receive: Pitching Prospects Griffin Herring and Josh Grosz
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Similar to shortstop, third base was a position for the Yankees that significantly needed an upgrade. Oswald Peraza and Jorbit Vivas struggled offensively and defensively, and the Yankees even tried moving starting second baseman Jazz Chisholm Jr. to the hot corner for a short period of time.
The chaos all ended in late July, when the Yankees acquired Ryan McMahon from the Colorado Rockies for two pitching prospects. McMahon played in 54 regular-season games for the Yankees to end the season, and while he wasn’t great on offense, that all changed in the postseason. Despite a small sample size, McMahon hit .286 in the postseason with an .833 OPS, significantly helping a stagnant Yankees offense.
Of course, his superb defense made him a net-positive on the field. At season’s end, McMahon was nominated for a Gold Glove, further highlighting his defensive efforts at the third base position.
Barring any changes, McMahon will be back as the Yankees’ starting third baseman in 2026. His left-handed swing is tailor-made for Yankee Stadium, so if the defense remains Gold Glove caliber, McMahon might be in for an excellent full season in the Bronx.
Grade: B
Yankees Acquire Jake Bird for Prospects
Yankees Receive: Relief Pitcher Jake Bird
Rockies Receive: Pitching Prospect Ben Shields and Infield Prospect Roc Riggio
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Of all the bullpen moves the Yankees made at the deadline, this one was the worst. However, it’s not for the reason you may think. Sure, Jake Bird posted six earned runs in three appearances for the Yankees before being optioned to the minors. However, to get him, the Yankees gave up one of their best prospects, infielder Roc Riggio.
In 40 games for the Somerset Patriots, the Yankees’ Double-A affiliate, Riggio went deep 11 times, drove in 28 runs, and posted an OPS .877. This was after his promotion from the Hudson Valley Renegades, the Yankees’ High-A affiliate, where Riggio drove in 15 runs in 20 games, had an OPS of 1.033, and far outplayed his competition.
The Yankees’ current bullpen is thin, so Bird will likely get a chance to prove himself in 2026. However, he’ll need a very good season to validate what Brian Cashman gave up to acquire him.
Grade: D+
Yankees Trade Trio of Prospects for David Bednar
Yankees Receive: Relief Pitcher David Bednar
Rockies Receive: Outfield Prospect Brian Sanchez; Infield Prospects Rafael Flores and Edgleen Perez
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Is there a letter grade above A? If so, that’s what this trade deserves. Game after game in 2025, the Yankees watched their bullpen struggle. Devin Williams, the prized acquisition of the offseason, simply couldn’t close games. Luke Weaver and Mark Leiter Jr. couldn’t finish the job either, putting an insurmountable amount of pressure on Brian Cashman to trade for a closer. Cashman answered the call, acquiring David Bednar from the Pittsburgh Pirates.
The rest, as Yankee fans know, is history. Bednar was lights-out for the Yankees, pitching to a 2.19 ERA in the regular season while allowing one single run in five postseason appearances.
The Yankees’ bullpen entering 2026 has a lot of question marks. Bednar, though, isn’t one of them.
Grade: A
Yankees Snag Camilo Doval From Giants
Yankees Receive: Relief Pitcher Camilo Doval
Giants Receive: Infield Prospect Parks Harber, Catching Prospect Jesus Rodriguez, and Pitching Prospects Trystan Vrieling and Carlos De La Rosa
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Camilo Doval had an up-and-down two months with the Yankees. He looked great at times, especially in the final two weeks of the regular season when he didn’t allow a run in six straight games. However, he struggled mightily with his command at times, an issue that followed him from his time with the San Francisco Giants.
In his defense, he went from closing games with the Giants to being a setup man for the Yankees. His role was never clearly defined, which likely caused some of his struggles. With a full offseason, though, his role should be clearer, and his command should be much improved.
Grade: B-
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