The MLB Trade Deadline has come and gone, and just like every season, it was chaotic. On trade deadline day alone, 50 deals were made. Some teams try to plug holes on the roster and add the final piece to make a push for October. Others sold off veteran, expiring contracts for young pieces in hopes of developing them into key contributors. We recently released our three winners of the trade deadline. But just because you made a trade, it does not mean it was the smart one. Here are the three losers of the 2026 trade deadline.
The 3 Biggest Losers of the MLB Trade Deadline
Milwaukee Brewers: It is weird to see arguably the best team in the majors as a trade deadline loser. With them having a comfortable lead in the NL Central and a lock for a playoff spot, you think they would not need much help. But it was clear that the Brewers needed pitchers. They needed to add at least one frontline starter to pair with Jacob Misiorowski. Instead of getting that star, they settled for Dustin May and a couple of relievers. They also got Bo Naylor for depth.
These moves feel like they make the Brewers a better regular season team, but not one that can make a deep run in the playoffs. Sure, a deep bullpen is a must, but May is not someone you feel comfortable starting a playoff game. They needed to be aggressive like they were when they got CC Sabathia back in 2008. They should have gone all in and traded for someone like Tarik Skubal, Freddy Peralta, or Jose Soriano. That would have given them a dominant one-two punch and a rotation that could carry them to a World Series. Instead, this team feels destined to come up short again.
Cincinnati Reds: The Reds were one of the quieter teams at the deadline. They only made two moves at the deadline. One was moving Nathaniel Lowe to the Cleveland Guardians in exchange for Juan Brito and Alejandro Rivera. The other one was sending Caleb Ferguson to the St. Louis Cardinals for International Bonus Pool Space. But many thought the Reds would be one of the more aggressive sellers at the deadline. With six contracts set to expire, the thought was they would move all of them for prospect return.
Sure, prospects at the trade deadline rarely pay off, but to let free agents walk for nothing is not a smart move. Why not grab some young players as lottery tickets, and see if you can develop them into anything? With the Reds having one of the weakest farm systems in the league, this was the perfect opportunity to infuse it with some talent. The Reds are heading for the same fate the Los Angeles Angels are in. The roster is not good enough to make the playoffs, and there is no big prospect coming up to change things.
New York Yankees: At first glance, the Yankees seemed to have a solid deadline. They got Luis Garcia Jr., who was the NL leader in slugging percentage, and seems like he was made to hit in Yankee Stadium. They also got Heliot Ramos from the San Francisco Giants, who is a fantastic defensive outfielder and has crushed left-handed pitching. A perfect platoon option and defensive replacement. They also moved the struggling Camilo Doval in an addition-by-subtraction move.
But the main reason why they lost the deadline is they did not do enough. Sure, the two moves that brought Garcia and Ramos will help the Yankees. But they still have major question marks in the bullpen and at catcher. Especially after it was announced that Ben Rice will stay at first and won’t go behind the dish this season. It feels like another season where the Yankees did not go all in. They cared about retaining prospects or not taking on too much salary, instead of doing whatever it takes to win. With how weak the AL is, it is inexcusable.
