2 Biggest Winners and Losers Following the 2026 MLB Trade Deadline

Some major moves were made, while other contenders didn't add much

Detroit Tigers starting pitcher Tarik Skubal (29) walks off the mound against the Baltimore Orioles at Comerica Park in Detroit on Wednesday, July 29, 2026. | USA TODAY Network via Reuters Connect

The 2026 MLB trade deadline has officially come and gone.

Multiple teams addressed some major areas of need. On the other hand, some contenders elected to make only a handful of moves, leaving their fan bases clamoring for more. Here are just a couple of the biggest winners and losers from this year's trade deadline.

Winner: Dodgers

Jul 18, 2026; Anaheim, California, USA; Detroit Tigers pitcher Tarik Skubal (29) throws against the Los Angeles Angels during the first inning at Angel Stadium. Mandatory Credit: Gary A. Vasquez-Imagn Images | IMAGN IMAGES via Reuters Connect

How can the back-to-back World Series champions not be the biggest winner of the trade deadline after adding the back-to-back American League Cy Young Award winner?

The Los Angeles Dodgers made the move that many baseball fans anticipated when they traded for Detroit Tigers ace Tarik Skubal. While the southpaw is technically a rental for the rest of this season, several pundits expect the Dodgers to show interest in signing the 29-year-old in free agency. But before then, the left-hander will now have an opportunity to play a big role in Los Angeles' quest for a three-peat.

Loser: Yankees

May 29, 2026; West Sacramento, California, USA; New York Yankees right fielder Aaron Judge (99) sits in the dugout before the start of the game against the Athletics at Sutter Health Park. Mandatory Credit: Cary Edmondson-Imagn Images | IMAGN IMAGES via Reuters Connect

The New York Yankees were widely expected to target bullpen and catching help at the deadline. They did not address either of those areas via trade.

Instead, the Yankees acquired Washington Nationals lefty-swinging slugger Luis García Jr. and San Francisco Giants outfielder Heliot Ramos. While both players should improve New York's offense, other issues seemingly remain with the team's current roster. It's also unclear whether three-time MVP Aaron Judge will play again this season.

Winner: Cubs

Aug 1, 2026; Toronto, Ontario, CAN; Toronto Blue Jays pitcher Kevin Gausman (34) pitches to the St. Louis Cardinals during the first inning at Rogers Centre. Mandatory Credit: Kevin Sousa-Imagn Images | IMAGN IMAGES via Reuters Connect

The Chicago Cubs desperately needed to add pitching at the deadline—and that's exactly what they did. Chicago acquired veteran right-handers Kevin Gausman and Clay Holmes, as well as reliever Ryan Zeferjahn.

Gausman and Holmes both have playoff experience. Holmes, in particular, is known for inducing ground balls, which should work well with the Cubs' strong infield defense. The former closer is working his way back from a right fibula fracture suffered in May, though. But still, Chicago did a solid job of aggressively attacking an area of need at the deadline.

Loser: Brewers

Aug 2, 2026; Anaheim, California, USA; Milwaukee Brewers pitcher Jacob Misiorowski (32) throws against the Los Angeles Angels in the first inning at Angel Stadium. Mandatory Credit: Jon Endow-Imagn Images | IMAGN IMAGES via Reuters Connect

The Milwaukee Brewers are obviously still one of the best teams in the majors this year. But after reportedly being involved in the Skubal sweepstakes and coming up short, Milwaukee ended up acquiring pitchers Dustin May, JoJo Romero, and Antonio Senzatela.

While those three arms may become valuable additions to a team with World Series aspirations, many fans thought the Brewers could have targeted one of the other big-name starters on the market to pair alongside Jacob Misiorowski.