By admin 
The MLB trade deadline is an annual game of chicken. There are buyers, there are sellers, there are big names, and there are depth moves. There are teams that delude themselves into thinking they could buy to their own detriment, and there are situations where sellers try to fool contenders into ponying up valuable prospects to make a run at the World Series.
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Except for their do-nothing 2023 deadline, the Yankees have been firm buyers at the trade deadline in every year of the Aaron Judge era, and even as injuries have dramatically heightened urgency and even caused some pause in the fanbase, the team has won 11 of 16 entering Thursday afternoon and sit in prime position to be aggressive to go win the AL East and a second pennant in three years.
Almost all deadline moves make sense for a team, with few exceptions, but the hit rate is not nearly as high. For one reason or another, some obvious moves fall apart fast, much to the chagrin of the fanbase and front office. Some of Brian Cashman’s biggest deadline moves in the last decade have blown up spectacularly, even when they were universally lauded at the time.
Unfortunately, maximum hindsight will be used here, even if unfair. The good news? The Yankees have not traded away a future superstar at the deadline. The bad news? Some of the guys they have traded could’ve helped!
Honorable Mentions
Andrew Heaney trade (2021): It’s less about what they gave up, as both Janson Junk and Elvis Peguero have bounced around and likely wouldn’t have been much use to the team the last few years, and more about how dreadful Heaney was in pinstripes. 7.32 ERA in 13 games and 35.2 innings never was going to play.
Striking out with the bullpen (2024): The Yankees had a good bullpen in 2024, but still added a pair of arms at the deadline to bolster it. They didn’t give up much, as Ben Cowles, Jack Neely, and Brandon Lockridge are heavily replaceable Quad-A guys. Still, they were probably kicking themselves with just how ineffective Enyel De Los Santos was and how Mark Leiter Jr.’s great stuff and peripherals never turned into results in his year and a half in pinstripes
A curiously quiet deadline (2023): Inactivity is also being counted here. The Yankees were right not to buy at the 2023 deadline with a 55-51 record through the end of July, sitting in last place in the AL East without Aaron Judge. But they should’ve sold off a few guys, especially Harrison Bader, who they just waived at the end of August anyway. It’s no big deal, though. Arguably their biggest trade chip, Clay Holmes, was a big part of the 2024 bullpen’s success en route to the World Series.
No. 5. Acquiring Jake Bird (2025)
Date: July 31, 2025
Yankees receive: RHP Jake Bird
Rockies receive: 2B Roc Riggio, RHP Ben Shields
Trades usually need more than one calendar year to make such declarative statements, but with a lack of an obvious No. 5, I’ll elect to call it early on a trade that will not age well, even if the prospects you traded don’t look like anything to lose sleep over.
After hitting up Colorado to acquire Ryan McMahon a few days prior, Cashman swung another trade with the lowly Rockies to get a reliever with good stuff and upside. While we’re currently seeing that the thought process was good to get such an archetype out of Coors Field (Angel Chivilli looks awesome), Bird has been an abject disaster in pinstripes.
A horrific first impression didn’t get much better this season, as he’s ridden the Scranton shuffle while pitching to an unsightly 7.24 ERA across 32.1 innings dating back to last August. Nothing is encouraging under the hood, either. It’s hard to see him getting another extended chance in 2026, and even though his biggest asset was his team control, it’s hard to envision the Yankees having that much patience with him.
While Shields has battled injuries as an already older prospect, Riggio is carving out a nice role for himself as one of the better hitters in the Eastern League down in Double-A. Scouts still aren’t super high on him long-term due to a concerning hit tool, but he’d be good organizational depth if the Yankees retained him past the deadline and could’ve added to the shallow position player depth in the farm system.
No. 4: Backing out of the Jack Flaherty trade (2024)
Not much is known about the situation with the Yankees and Jack Flaherty at the 2024 trade deadline, but The Athletic reported just after the deadline passed that the Yankees and Tigers had agreed to a deal for Flaherty that was nixed because of concerning medicals regarding a recent back injury. A few hours later, the Dodgers swooped in and got the breakout right-hander for Thayron Liranzo and former Yankees first-round pick Trey Sweeney.
In 10 starts down the stretch for the eventual World Series champions, Flaherty pitched to a 3.58 ERA in 55.1 innings with 61 strikeouts before an inconsistent playoff run, where he threw seven shutout innings in NLCS Game 1 against the Mets and 5.2 solid innings in Game 1 against the Yankees, but struggled mightily in his other two starts in those series.
Still, the reason this is on this list is because of how thin the Yankees’ rotation was beyond Gerrit Cole and Carlos Rodón. Relying on Clarke Schmidt and 2024 Rookie of the Year Luis Gil to start games in the World Series was never a great formula, so acquiring Flaherty would not only have given you a third experienced arm but also taken away from a Dodgers squad that limped into that World Series with only Flaherty, Yoshinobu Yamamoto, and the husk of Walker Buehler.
The prospect cost not being known complicates this. Maybe the Yankees had to send something that would’ve led to a domino effect, making them worse. Maybe Flaherty’s back acts up, and he misses the postseason as James Paxton did in 2020. We’ll never know what happened if Cashman pulled the trigger, but it’s a sour taste in your mouth nonetheless.
No. 3: Acquiring Frankie Montas (2022)
Date: August 1, 2022
Yankees receive: RHP Frankie Montas, RHP Lou Trivino
Athletics receive: LHP Ken Waldichuk, RHP Luis Medina, LHP JP Sears, INF Cooper Bowman
This is another move that, without hindsight, isn’t too bad. Despite past injury issues with Montas, he was clearly the second-best pitcher on the market behind Luis Castillo, who went for an absolute haul to a team with a better farm system. The Yankees gave up a top-100 prospect of their own in Waldichuk, but ultimately left feeling good.
Unfortunately, this was a disaster. Montas didn’t easily adjust to the weight of the pinstripes and faltered in eight starts after the deadline, pitching to an unsightly 6.35 ERA in 39.2 innings before being shut down with a shoulder injury in mid-September. Montas’ injury had popped up as an issue before being traded. It’s one of those things that could’ve been prevented, but the Yankees overlooked it.
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The following season, he re-injured his shoulder in February and eventually underwent surgery, missing the entire season aside from one game in late September, when he pitched 1.1 innings before hitting free agency and jumping ship to the Reds. Montas’ tenure was a pure disaster, and the way his pre-existing injuries were ignored was likely the catalyst behind the team’s restraint for Flaherty two years later. Each move impacts the next, and this was a prime example.
Even the one part of the trade that seemed like a success fell apart. Trivino was one of the team’s best relievers down the stretch in 2022, posting a 1.66 ERA across 21.2 innings in 25 appearances. But he underwent Tommy John surgery in 2023 and never put on the pinstripes again.
The saving grace is that they’re not exactly hating what they gave up. Waldichuk was a big “sell high” guy and struggled in Oakland over the next two seasons before undergoing Tommy John surgery. Now on the 60-day IL in Washington, he has a 5.35 career ERA in over 180 innings. Bowman was a high draft pick who still hasn’t debuted and is currently out of baseball after being released by the Rays in April.
Sears, who debuted with the Yankees in 2022, was a model of consistency over the next three seasons, not missing a start and tallying a 4.59 ERA across 95 starts with the A’s before being lumped in the Mason Miller trade. Could the Yankees have used him as depth, particularly because he’s just been a Walmart Will Warren? Sure, but he’s also now battling injuries this year with the Padres.
The only part of this trade still with the Athletics is Luis Medina, who’s finally figured it out in 2026. The electric flamethrowing righty was moved to the bullpen after missing 2025 due to an injury. He has posted a 3.70 ERA with 58 strikeouts in 48.2 innings and a large, but acceptable walk rate.
No. 2: Inactivity at the worst time (2019)
The 2019 Yankees were really good, and the 2019 trade deadline was eerily quiet, but the fact that not a single trade was made in July for the eventual 103-game winners is absurd to this day.
Despite having a stacked lineup and bullpen, there was still a clear need in the rotation. Paxton and Masahiro Tanaka were a formidable 1-2 punch, but losing Luis Severino to injury made the unit an uncertainty come playoff time, so while Sevy would return down the stretch, they needed another proven guy.
The rumor mill swirled about Marcus Stroman as a potential option, but the big fish was the Diamondbacks’ future Hall of Famer Zack Greinke. Even getting a somewhat decent starter would’ve been nice, but they did nothing outside of a June trade for Edwin Encarnacion. Not getting a starter at the deadline forced the Yankees to use an opener in Game 6 of the ALCS against the Astros because of necessity.
And who got Greinke, you ask? The team that beat you in that ALCS, of course. Outside of the 2024 team, the 2019 team was as talented as any in the Judge era. But didn’t get any reinforcements when they were needed.
No. 1: Acquiring Joey Gallo (2021)
Date: July 29, 2021
Yankees receive: OF Joey Gallo, LHP Joely Rodriguez
Athletics receive: UTL Josh H. Smith, UTL Ezequiel Duran, RHP Glenn Otto, OF Trevor Hauver
The Joey Gallo trade was a slam dunk when it was made. You’re getting an All-Star left fielder to add alongside Judge and Stanton, creating the most powerful Big 3 in MLB history, with 1.5 years of control. You also gave up a package that many believed was a major underpayment.
As we all know, it didn’t work. Gallo was the consummate “not built for New York” acquisition, immediately letting the bright lights get to him and feeling the wrath of Yankees fans when he hit under the Mendoza line and struck out 40 percent of the time on his way there. In 140 games over two partial seasons, he slashed .159/.291/.368 with an 84 OPS+ before being traded at the following year’s deadline to the Dodgers for Clayton Beeter, who was flipped three years later for Amed Rosario.
The Yankees also acquired a reliever in Rodríguez as a lefty specialist, and he pitched well in 19 innings down the stretch, but was flipped the following March to the Mets for Miguel Castro. One singular year after this trade, the Yankees had already given up on both players they acquired.
Both Smith and Duran would go on to be contributors to the Rangers’ 2023 World Series championship, albeit in different ways. Duran broke out in that 2023 season as a utility starter before slumping mightily over the next two seasons.
He’s back to 2023 form, and playing around the diamond in 2026, and currently stands as the guy the Yankees most wish they still had. Smith won a Silver Slugger in 2024 and has been better over the course of his tenure, but has struggled in 2026.
Neither Otto nor Hauver has become anything. The former is out of baseball after posting a 5.62 ERA over 170 innings from 2021-23, while Hauver is still toiling in Triple-A with the Rangers but is running out of time as he nears his 28th birthday without a 40-man roster spot.
Today’s best reads
- Jasson Dominguez, Spencer Jones Failing to Meet Expectations Should Force Yankees to Hit Trade Market
- Yankees Need New OF Trade Target as Spencer Steer Lands on IL
- Yankees Must Resist Temptation of Trading Clarke Schmidt at the Deadline
- Brian Cashman’s Best Trade Deadline Move Might Be One Yankees Fans Least Expect
- Yankees Monday Mailbag 7/27: Outfielder Trade, World Series Run, and Dealing Jasson Domínguez
This article was originally published on www.si.com/mlb/yankees/onsi as Ranking the Yankees’ Five Worst Deadline Moves in the Aaron Judge Era.
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This story was originally published July 30, 2026 at 10:00 AM.