When you've been at the helm for as long as New York Yankees general manager Brian Cashman has, you're bound to have attacked the trade deadline in every way possible. The upcoming July 31 deadline will be Cashman's 27th calling the shots (though some of the earlier years featured some "heavy input" from The Boss), and over that time, we've seen some trends emerge.
The game has changed a lot since the heyday of the last great Yankee dynasty, so when predicting what Cashman might do or who he might target, recent history should hold more weight.
In recent years, Cashman has shown a considerable preference toward bringing in players, especially position players and starting pitchers, with some degree of control remaining, though even relievers can tempt the long-time executive if they come with years of control.
Other traits that get his motor running seem to be athleticism, potential upside, defensive prowess, and versatility. Look no further than last year's deal to acquire Jazz Chisholm Jr. or 2022's move to acquire the glove-first Harrison Bader as prime examples.
There's been a surprising lack of star-level mercenaries coming through the Bronx as half-year rentals, indicating that, at least recently, Cashman prefers to bet on upside, even if a player hasn't reached his full potential.
With a sizeable list of needs, one of which has become significantly more dire in the wake of Clarke Schmidt's injury, it's important to consider these recent preferences and evaluate the presumed crop of players on the trade block through this prism.
These 4 players look like perfect Brian Cashman trade targets as the Yankees gear up for October
Pittsburgh Pirates third baseman Ke'Bryan Hayes
Young? Check! Ke'Bryan Hayes is just 28 years old. Athletic? Check! Hayes is a former top prospect who looked to be a future star if he could ever translate his athletic gifts to the diamond. Defense? Check! As of July 4, Hayes leads all MLB third basemen in defensive runs saved with 12, and a significant gap exists between him and the runner-ups: Seattle's Ben Williamson and former Yankee farmhand Caleb Durbin, who have posted seven DRS apiece.
Add in years of control (Hayes signed an extension in 2022 that takes him through at least 2029 at an AAV of $8.75 million) and a familiar trading partner in the Pittsburgh Pirates, and this is starting to feel like a Brian Cashman special.
The Yankees' need at third base is great, and the defense would be upgraded considerably with Hayes following in his father's footsteps and manning the hot corner in the Bronx, while Jazz Chisholm Jr. shifts back to his happy place at second, where he, too, is a premium defender.
There's one problem, though. Hayes can't hit. After a career year in 2023, which saw him post a .271/.309/.453 line that was good for an exactly league-average 100 wRC+, Hayes followed that up with a 2024 performance that was the worst of his career, posting a 59 wRC+. Things haven't gotten much better for the defensive wizard, as his .247/.297/.304 line has produced a powerless 68 wRC+ on the season.
All we can do is hope that Cashman resists his impulses and finds the Yankees a much more suitable option to fill out the infield at the deadline.
Miami Marlins starting pitcher Edward Cabrera
All eyes will be on where 2022 NL Cy Young winner Sandy Alcantara ends up; however, it's a different Marlins hurler who could become the apple of Cashman's eye and coax the Yankees' decision maker to go back to the well and trade with the Marlins for the second straight year.
Alcantara's 7.01 ERA in his first season back from Tommy John is likely a non-starter, but his rotation mate Edward Cabrera's shiny 3.41 mark would certainly look good supporting Max Fried and Carlos Rodoón in the Bronx.
Cabrera, 27, is under team control through 2028 and has an electric right arm, even if the production hasn't always been there. The biggest red flag, however, is his laundry list of injuries, which have prevented him from ever topping 20 starts or reaching the 100-inning plateau over his five-year career.
This move would have the feel of the Frankie Montas trade: an injury-prone starter with potential and some control over the coming years. Minus the injuries, this also harkens back to the Sonny Gray deal from 2017. If Cashman does go the Cabrera route, let's hope it works out better than his previous ventures down this path.
Colorado Rockies reliever Jake Bird
Even with Devin Williams mostly righting the ship and Luke Weaver returning from the injured list, the Yankees' bullpen has been increasingly unreliable as the season has gone on. Fernando Cruz is hurt again, Jonathan Loaisiga is proving to be a huge mistake, and the likes of Mark Leiter Jr. and Ian Hamilton need to be as far away from high-leverage situations as possible.
That means New York will likely go bullpen shopping. As luck would have it, the market is pretty flush with options. Not needing a closer means the Yankees can be a bit pickier about who they choose, and history tells us that Cashman may favor options that will stick around beyond this season.
One player who could make a ton of sense is Colorado Rockies reliever Jake Bird. Bird's market is heating up as his breakout season continues with career-bests in both ERA (2.79) and strikeout rate (28.6%).
The 29-year-old righty begins his three years of arbitration in 2026, and still has two minor-league options remaining, giving Cashman the flexibility he craves both now and for the future. That amount of control will drive up his cost, but on the flip side, not having the closer tag attached to his name will devalue him a bit.
Cashman has gone this route before when he needed to shore up the bridge to his big guns in the late innings, to varying degrees of success. Tommy Kahnle's first go-around with the Yankees saw this strategy work (for the most part), while the Scott Effross version of this maneuver has been an abject failure.
Given Cashman's past history, Bird feels like the type of reliever he'd hone in on, especially with both Weaver and Williams hitting free agency in the offseason.
Minnesota Twins second baseman/utility man Willi Castro
There's a good chance that Cashman will decide he wants to have maximum flexibility when it comes to solving the Yankees' infield problem, and Willi Castro of the Minnesota Twins could be just the guy to give it to him.
So far this season, Castro has logged time at second base, shortstop, third base, and all three outfield positions, if you include his one inning in center this year. This kind of bouncing around the diamond has become something the 28-year-old has become accustomed to over his seven-year career.
That defensive versatility would allow Aaron Boone time to figure out the optimal alignment for everyone, while also having an insurance policy for the outfield should an injury arise. As a switch-hitter, that versatility would extend to the batter's box as well.
One thing Castro doesn't provide is control, as a free-agent-to-be, but Cashman could be swayed by his ever-improving performance since leaving the Detroit Tigers for the Twins ahead of the 2023 season. His 2025 line of .274/.362/.435 is a career-best and builds on the solid performances he turned in in 2023 and 2024.
There is another drawback, though. Castro is not a good defender, with -10 DRS total across his array of positions.
Still, Castro could be up Cashman's alley because acquiring him wouldn't preclude the Yankees from also nabbing a third baseman, should an advantageous situation present itself. As a standalone option to take over second base, his most commonly played position aside from the outfield, he works, but he also functions as a super utility man, putting an end to the Oswald Peraza experience.
