The trade deadline is always a critical point in the MLB season, where teams must decide whether to reinforce their rosters for a playoff push or sell off assets and focus on the future. This year, several teams found themselves at a crossroads, with opportunities to either make bold moves or settle for incremental upgrades. Some teams, however, failed to capitalize on these opportunities, ultimately staying stuck in mediocrity or missing out on potential game-changing trades. Here are the 3 teams that had the worst trade deadlines in the MLB 2025 season:
3. Boston Red Sox
After trading Rafael Devers to the San Francisco Giants, many believed the Red Sox were effectively punting on the season—and with good reason. They were sitting at 37-36 and appeared to be heading toward a steep decline. However, the opposite happened. The Sox improved, winning 25 of their next 40 games, and positioned themselves in the 3rd Wild Card spot as the trade deadline approached.
While the Red Sox didn't necessarily need to make any team-altering moves given their young core, they had an opportunity to strengthen their postseason push by acquiring starting pitching. Unfortunately, they didn’t seize it. They watched Merrill Kelly join another AL contender, the Texas Rangers, and only managed to acquire Dustin May, who is 6-7 with a 4.85 ERA, a 1.35 WHIP, and a history of injury concerns. With Tanner Houck already sidelined for the rest of this year and all of next season due to Tommy John surgery, the Red Sox should have targeted a starting pitcher with control. Dustin May, set to become a free agent at the end of this season, doesn't fit that bill.
However, their acquisition of RP Steven Matz was a solid move. While sending Blaze Jordan to the Cardinals may seem like a steep price, Jordan is Rule 5 eligible next season and is blocked by other players in the MLB.
2. Los Angeles Angels
The Los Angeles Angels currently sit at 53–58, 5.5 games back of the final wild card spot. Heading into the trade deadline, the Angels had two clear options: go all in or commit to a sell-off. With superstar Mike Trout aging and the team stuck in mediocrity, they desperately needed to pick a direction—and they didn’t.
Instead, the Angels made two minor moves. On July 31, they acquired INF Oswald Peraza from the Yankees in exchange for OF Wilberson De Pena and international bonus pool money. The day before, they picked up LHP Andrew Chafin and RHP Luis García from the Nationals for LHP Jake Eder and INF Sam Brown. These deals were half-measures. Chafin is the only notable addition, but even he comes with red flags, as despite a 2.70 ERA, his 1.60 WHIP and 3.74 FIP suggest regression is coming.
Once again, the Angels find themselves without a clear direction. With the way closers were valued at the deadline, they could have landed a haul of prospects for Kenley Jansen. And with OF Taylor Ward entering his final year of arbitration this winter, he, too, could’ve brought back strong returns. Instead, the Angels remain stuck in limbo.
1. Chicago Cubs
The Chicago Cubs currently sit as the second-best team in the National League with a 64–46 record. While many of their NL rivals made bold moves to bolster their rosters, the Cubs opted for a more conservative approach, adding a few pieces that, while serviceable, are far from headline-grabbing. They acquired utility player Willi Castro from the Twins, reliever Andrew Kittredge from the Orioles, and starting pitcher Mike Soroka from the Nationals.
Castro has been a solid contributor for Minnesota this season (.245/.335/.407), but he remains a utility player and represents only a modest upgrade. Kittredge has been steady but unspectacular out of the bullpen, posting a 3.45 ERA and 1.09 WHIP. Soroka, meanwhile, has struggled in 2024, recording a 4.87 ERA despite a decent 1.13 WHIP.
While these additions help round out the roster, they don’t move the needle much. With the future of star outfielder Kyle Tucker uncertain, this may have been the ideal moment for the Cubs to push their chips in, especially in a wide-open National League where the path to the pennant feels more attainable than usual.
While not all of these teams needed to decide on the direction of their respective franchises, they all missed the mark on what would have been a successful deadline. However, while the trade deadline is very important, we often put too much emphasis on it. Only time will tell how the futures of these organizations shape up through the rest of this season and beyond.
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