MLB Trade Deadline Mistakes: 5 Teams Who Failed at the Deadline?
Grant White
Host · Writer
Boston Red Sox
The Boston Red Sox saw most of the American League playoff teams around them get better. Their move was to add a pitcher who is going to struggle in Beantown.
Dustin May was once regarded as a top-of-the-rotation arm for the Los Angeles Dodgers. However, after undergoing Tommy John surgery, he has lost his most electric stuff. May sits in the bottom 22nd percentile in hard-hit rate, average exit velocity, and expected ERA. Settling into the hitter-friendly confines of Fenway Park will be an exercise in futility.
Chalking this up as a mistake is as polite a euphemism as they get. At this rate, the Red Sox are destined for another century-long drought between championships.
Tampa Bay Rays
It looks like owner Stu Sternberg is going full scorched earth before he sells the Tampa Bay Rays.
We knew the Rays would be busy at the trade deadline; they always are. But you can't help but scratch your head at some of the moves they made.
While the playoff hopefuls made some much-needed upgrades to their bullpens, they lost two reliable arms in Zack Littell and Taj Bradley. More confusingly, the team elected to trade away their most versatile defender, Jose Caballero, partway through a game in which they had lost several players to injury.
The Rays' moves amount to net zero, if not detract from their playoff chances. They may have bid adieu to their postseason aspirations without any meaningful additions.
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Miami Marlins
The Miami Marlins weren't dealing from a position of strength, but they rarely are. A perennial basement dweller, the Marlins will be spending more time at the bottom of the standings for years to come.
Granted, the team moved on from Jesus Sanchez, but the return was less than promising. Sanchez was one of the most coveted left-handed bats on the market, and Miami got two faltering prospects (Chase Jaworsky and Esmil Valencia) and a pitcher who has seemingly caught lightning in a bottle (Ryan Gusto) as the return.
They also failed to move Sandy Alcantara and Edward Cabrera, a pair of arms that could have brought in a haul of prospects.
Whatever Marlins fans remain have surely given up on ever seeing a competitive baseball game again.
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San Francisco Giants
After months of mounting evidence, it turns out Rafael Devers was the problem all along. Still, the San Francisco Giants decided to stand pat with their roster, a decision that will result in their untimely demise.
The Giants were hanging tough in the ultra-competitive NL West for the better part of the season. But with just two wins over their last 14 games, they desperately needed some sort of roster shakeup to get back to neutral.
Despite falling metrics, limited run production, and ineffective pitching, San Francisco elected to maintain the status quo. The teams ahead of them in the standings got better. Somehow, the Giants continue to get worse.
MLB Trade Tracker: Every Player Dealt at the 2025 Trade Deadline
Athletics
Every time the Athletics find a foundational piece, it's just a matter of time before they decide to move on from their potential cornerstone. That was the case again this deadline, as the A's decided to part ways with electric closer Mason Miller.
One thing we can't fault the Athletics on is the return they got for Miller. Rightfully, the A's got one of the top prospects in baseball, landing Leo De Vries from the San Diego Padres. It will be impossible to replace Miller's production, but the Athletics did get three pitchers in return.
Still, it's just a matter of time before De Vries and the rest of the A's farm are sold off for more future assets. With that, the perpetual cycle of substandard baseball continues.
Boston Red Sox
The Boston Red Sox saw most of the American League playoff teams around them get better. Their move was to add a pitcher who is going to struggle in Beantown.
Dustin May was once regarded as a top-of-the-rotation arm for the Los Angeles Dodgers. However, after undergoing Tommy John surgery, he has lost his most electric stuff. May sits in the bottom 22nd percentile in hard-hit rate, average exit velocity, and expected ERA. Settling into the hitter-friendly confines of Fenway Park will be an exercise in futility.
Chalking this up as a mistake is as polite a euphemism as they get. At this rate, the Red Sox are destined for another century-long drought between championships.
Tampa Bay Rays
It looks like owner Stu Sternberg is going full scorched earth before he sells the Tampa Bay Rays.
We knew the Rays would be busy at the trade deadline; they always are. But you can't help but scratch your head at some of the moves they made.
While the playoff hopefuls made some much-needed upgrades to their bullpens, they lost two reliable arms in Zack Littell and Taj Bradley. More confusingly, the team elected to trade away their most versatile defender, Jose Caballero, partway through a game in which they had lost several players to injury.
The Rays' moves amount to net zero, if not detract from their playoff chances. They may have bid adieu to their postseason aspirations without any meaningful additions.
Swing for the Fences with SportsGrid’s free daily MLB Game Picks and MLB Prop Picks.
