Hindsight is 20/20, and that's what makes what I do so much easier than doing what an MLB GM does. Thanks to the power of hindsight, it's rather easy to call out execs who made mistakes at the trade deadline. Some trades have aged poorly, but the decision to hold onto some trade candidates has backfired, too.
What this offseason has shown us is that these six players should've been traded at last year's trade deadline for a variety of reasons.
RHP Pete Fairbanks, Tampa Bay Rays
The Tampa Bay Rays electing to hold onto Pete Fairbanks might be the most egregious decision on this list, at least in hindsight. Sure, the Rays were technically in the AL Wild Card race at the trade deadline, but they were under .500, and the odds of them actually doing much in the postseason (assuming they even made it there) were incredibly slim.
Relievers are always valuable at the trade deadline, and plenty of them get moved every year. Fairbanks, had he been dealt, would've been one of the best relievers on the market, and could've brought the Rays solid value in return.
Instead of trading him, though, the Rays held onto him, missed the playoffs and then wound up rejecting his club option, allowing him to hit free agency. Trading him for just about anything would've been better than keeping him, failing to make the playoffs and letting him walk, which is what ultimately happened.
LHP JoJo Romero, St. Louis Cardinals
I understand why the St. Louis Cardinals didn't want to go all-in on selling their team for scraps at the trade deadline. Chaim Bloom had not yet taken over as the primary decision-maker in the team's front office, so it made some sense only to trade away players on expiring contracts. Still, you can't help but wonder what the Cardinals could've gotten for an outstanding left-handed reliever like JoJo Romero, who is under control through only the 2026 season.
Teams pay a premium for valuable players who will be in town for more than just a couple of months. I don't know what the value is for just one year of Romero, as solid as he is.
St. Louis could still trade him this offseason for something decent, but teams can simply choose to sign a free agent like Danny Coulombe or Justin Wilson if they don't want to meet the Cardinals' asking price. It feels like the team could've gotten much more for Romero in July than they will if they trade him before he hits free agency, and that's a shame, since the Cardinals weren't competitive in 2025 and likely won't be in 2026 either.
OF Luis Robert Jr., Chicago White Sox
The Chicago White Sox confused everybody when they elected to hold onto Luis Robert Jr. rather than take what they could've gotten at the deadline. The White Sox, obviously, aren't going anywhere anytime soon, and it felt as if Robert, a player who had really struggled at the plate in each of the last two seasons, needed a change of scenery.
By holding onto Robert, the White Sox were hoping he'd finish strong in order to be traded this offseason for more than they could've gotten in July. While Robert did play better after the deadline, he also missed the final month of the season due to injury. Now, Robert still has as many questions as ever regarding his ability and durability, and he's also owed $20 million in 2026 with a $20 million club option for 2027.
Robert's value now is likely not any higher than it was in July, so there's a chance Chicago will hold onto him into the 2026 campaign and hope he bounces back while staying healthy. Perhaps he will, but we've been saying this for two years now. The longer they wait, the lower his value gets. The White Sox might've missed their best chance to move him.
RHP Ronny Henriquez, Miami Marlins
The Miami Marlins were one of the biggest pleasant surprises in the National League this past season, and Ronny Henriquez, a massive surprise in his own right, played a huge role in that. Henriquez, a waiver claim by Miami, was the team's best reliever, posting a 2.22 ERA in 69 games.
Sure, it obviously makes sense to want to hold onto an emerging reliever with five years of additional control, but imagine what the Marlins could've gotten had they traded him. Teams value control immensely, so a quality reliever with five years of control left could've brought Miami back something serious.
The Marlins shouldn't have sold low, obviously, but given the likelihood that they're still far away from being true World Series contenders, why not sell high? The fact that Henriquez is going to miss all of 2026 with an injury only validates the possibility of the Marlins missing their best chance to trade Henriquez for a haul.
OF Jarren Duran, Boston Red Sox
The Boston Red Sox had a "problem" at last year's trade deadline that 29 other teams wish they had: They had too many outfielders. This remains the case now, several months later. Roman Anthony, Ceddanne Rafaela, Wilyer Abreu and Jarren Duran are four outfielders fighting for three spots. Anthony, obviously, isn't going anywhere, and Rafaela, the best defender of the bunch who is locked in long term, probably isn't either. The Red Sox could trade Abreu, but Duran, an older outfielder who is closer to free agency, makes more sense to move.
Duran's name swirled in rumors around the deadline, but the Red Sox ultimately held onto him. His name has been prevalent in offseason rumors, too, but nothing has happened yet. At the end of the day, teams know that the Red Sox have more outfielders than spots to put them, and that Duran is the most likely to go. So no one is willing to meet Boston's asking price.
Craig Breslow might end up trading Duran this winter or sometime during the 2026 season, but it's feeling increasingly likely that the Red Sox missed their best opportunity to trade him.
2B Ketel Marte, Arizona Diamondbacks
This might be cheating a bit, as the Arizona Diamondbacks did not shop Ketel Marte at the 2025 trade deadline. But knowing what we do now, they would've been better off doing so for a couple of reasons. First, the Diamondbacks traded several veterans in exchange for prospects as they waved the white flag on the 2025 season. Sure, those veterans traded were all rentals, but a Marte deal would've made sense had the Diamondbacks received the kind of ridiculous return they're shooting for this offseason.
Second, shortly after the deadline it was revealed that Marte's fit in the clubhouse was far from perfect. MLB teams knowing this now gives them reason not to give Arizona their best offers, knowing the Diamondbacks might feel compelled to trade him just for a culture reset.
The Diamondbacks had to have known they would've considered trading Marte this offseason by the trade deadline, so why not try and move him then, when they weren't trying to win the 2025 World Series anyway? The fact that Arizona hasn't traded Marte to this point suggests they have not gotten an offer to their liking, and it's hard to believe that'll change anytime soon. That godfather offer could've been there at the deadline, though, especially since the best position players traded were a rental in Eugenio Suarez and an underwater contract in Carlos Correa.
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