New York Yankees and 4 MLB Teams Already Regretting Trade Deadline Moves
The reason that some executives would like to move the trade deadline back a couple weeks is it gives them more time to decide whether or not their team should be buyers or sellers.
Here we are on Aug. 17, and there's already a few teams who probably would (or should) like a mulligan. Granted, these are extremely short sample sizes, particularly for players who aren't rentals. Nonetheless, in the midst of a pennant chase, one or two bad moments can change the course of a season.
With that in mind, here's a look at five teams already regretting their trade deadline moves.
Pittsburgh Pirates
1 of 5
The Pirates remade their bullpen before the trade deadline in hopes that they could reach the postseason for the first time since 2015. So far, the results have not been good, as the Pirates are 61-65, 6.5 games out of the final wild-card spot in the NL.
Luke Weaver has only made three appearances since being acquired from the New York Mets, with his latest—four hits and three earned runs in a loss to the Boston Red Sox Saturday—part of what's been a very disappointing 6-9 start to August.
Camilo Doval, acquired from the Yankees, did pitch a scoreless inning in a Sunday victory. However, he's walked at least one batter in five consecutive appearances for the Buccos.
To be fair, 39-year-old Kirby Yates has pitched well since being acquired from the Los Angeles Angels. Yates struck out two and earned the win Sunday, and has a 2.89 ERA in his first seven appearances for the Pirates.
The bigger issue for the Pirates might just be that their core pieces aren't performing as expected and/or aren't healthy right now:
- Paul Skenes has a 5.13 ERA in five starts since the All-Star Break.
- Konnor Griffin—who entered the year as one of the NL Rookie of the Year favorites—hasn't played since tearing his left ring finger in early July.
- Oneil Cruz has been out with metacarpal fractures since June, and is currently on a rehab assignment.
- Ryan O'Hearn landed on the IL with a left quad strain just days before the trade deadline.
- Mitch Keller is out for the season with a teres major injury to his pitching shoulder.
As much as it was nice to see owner Bob Nutting spend a bit last offseason and authorize general manager Ben Cherington to add before the deadline, the Pirates may end up wishing they sold. Had the Pirates been sellers, there would have been plenty of interest in impending free agents like Brandon Lowe and Gregory Soto.
Detroit Tigers
2 of 5
It seems unlikely owner Chris Ilitch was going to allow president of baseball operations Scott Harris to make a competitive offer for two-time defending AL Cy Young Award winner Tarik Skubal in the offseason, so it's understandable that the Tigers moved him to the Los Angeles Dodgers.
With that said, it was a bit surprising that the Tigers dealt Skubal with more than 24 hours until the trade deadline.
It seems likely that Zyhir Hope, River Ryan and Brady Smith were a package the Tigers could have gotten 45 minutes before the trade deadline, and it's possible holding Skubal until the last minute would have netted an even larger return, whether from the Dodgers or another team.
Alternatively, there still has to be part of the Tigers that wonders what they could have been had they held onto both Skubal and Casey Mize, who was traded to the San Diego Padres.
As is, the Tigers are currently one game back of the final wild-card spot in the AL. If A.J. Hinch's club snuck into the postseason with a rotation that included Skubal, Mize and Framber Valdez, who's to say they couldn't have made noise in what may be the weakest AL in at least a generation?
Alas, moving Skubal and Mize was probably the right long-term move for Detroit. However, for at least the rest of the season, Harris and company will likely wonder what would have happened if they went the other route and potentially added a piece or two.
Baltimore Orioles
3 of 5
The Orioles have some similarities to the Tigers. They entered the season with World Series aspirations, but have disappointed. Still, they find themselves in control of the final wild-card spot in the AL, despite selling at the trade deadline.
While the Orioles also traded Adley Rutschman, Dean Kremer and Tyler Wells, moving Taylor Ward to the Seattle Mariners might be the one that is hardest to justify.
In return for Ward, the Orioles received RHP Alex Hoppe (5.17 ERA in 28 appearances), along with 26-year-old minor league reliever Brock Moore and 24-year-old RHP Harrison Kreiling, who is currently at Single-A. If the O's unlock Hoppe—who has a 98 mph fastball—this deal could prove very successful. It just doesn't feel like a sure enough thing to make this move when you're still in contention. If the Orioles were 10 games out of a playoff spot, so be it. But it's hard to tell your fans that you're putting your best foot forward to be competitive if you sell off one of the more accomplished bats in your lineup for what seems to be an underwhelming trade package.
Granted, Ward is an impending free agent, one who has gotten off to a slow start in Seattle. He homered 36 times last year for the Angels, but has just seven homers in 2026. However, Ward leads the junior circuit with 87 walks. It's not out of the question he could have helped the Orioles win an extra game or two, which may be the difference between reaching the postseason or not.
We're going to guess that the Orioles wouldn't have been comfortable extending Ward a qualifying offer in the offseason if they had held onto him, but having the QO in their back pocket seems like it would have been a pretty good insurance policy.
New York Yankees
4 of 5
Again, this list mostly focuses on the immediate impact—or lack thereof—that players have had on their new teams.
Luis García Jr. had 23 home runs and an .873 OPS with the Washington Nationals, and has one more arbitration year remaining in 2027. The Yankees will likely be happy in the long run that they traded for García, who mashes righties. It is worth noting, though, that so far he has a .653 OPS in pinstripes.
Heliot Ramos, acquired from the San Francisco Giants, has been even worse. Over his first 10 games with the Yankees, Ramos is batting just .063 with 11 strikeouts and zero RBI. He's under team control through the 2029 season, and has a history of crushing left-handed pitching.
There was, and still is, a lot to like about Ramos as a trade candidate. But the Yankees gave up two decent prospects—LHP Henry Lalane and shortstop Kaeden Kent—to acquire Ramos, so they need him to turn things around.
Let's face it, the Yankees aren't going to go far if some combination of Aaron Judge (stress fracture in right ribcage), Cody Bellinger (left hamstring strain) and Giancarlo Stanton (right calf strains) aren't healthy and productive when October rolls around.
However, part of the thought process in trading for García and Ramos was to tide the Yankees over, and so far that hasn't happened.
Kansas City Royals
5 of 5
Give the Royals credit: They are a small-market team, but they usually make a serious effort to contend, unlike many others in that category.
However, the Royals are 51-74. They made the playoffs and won a series in 2024, but have put together consecutive disappointing seasons since then. This current formula isn't working, and it's going to be very difficult for them to turn things around in one offseason.
With that in mind, they probably should have been willing to consider offers for Michael Wacha and/or Seth Lugo before the Aug. 3 trade deadline.
While Wacha is signed for $14 million in 2027, with an affordable club option for $14 million in 2028, he's 35 years old. By holding onto him, the Royals are risking he declines and/or gets injured for a team with nothing to play for down the stretch.
That's arguably even more true for Seth Lugo, who will turn 37 years old in November. He'll make $21.5 million in 2027, and has a $17 million conditional club option for 2028.
By trading Wacha and/or Lugo, the Royals could have improved their pipeline, while opening up money to reallocate resources.
Instead, president of baseball operations J.J. Picollo will have to figure out how to build a contending roster around Wacha and Lugo, who they haven't won with recently even as they've pitched well.
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