MLB Trade Fails That Will Keep Haunting Teams in 2026
At this point, it doesn't need to be said: The February 2020 trade that saw the Red Sox trade Mookie Betts, David Price and $48 million to the Los Angeles Dodgers for Alex Verdugo, Jeter Downs and Connor Wong was an unmitigated disaster for Boston.
There's probably no return that could have made giving up Betts at the height of his powers make sense, particularly since he's helped lead the Dodgers to three World Series titles in six seasons. But considering Verdugo is a free agent, Downs is playing in Japan and Wong is a part-time catcher, it burns even more that the Red Sox gave up an inner-circle Hall of Famer prior to his age-27 season.
Rightfully so, the Red Sox mishandling of Betts has been run into the ground by now. So here's some other MLB trade fails that will keep haunting teams in 2026.
Red Sox Botch Relationship With Rafael Devers So Badly They Have To Trade Him During Season
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It's universally accepted that the Red Sox blew it with the aforementioned Betts, which is why we didn't spend a full slide on him. However, Boston isn't absolved from their sins on this list.
While Rafael Devers probably could have handled things in a better fashion, the Red Sox clearly bungled their communication with him regarding moving him off of third base to sign Alex Bregman last winter, and then trying to get him to learn first base when Triston Casas was lost for the season.
Things got so ugly that the Red Sox pounced on a chance to offload Devers last June, sending him to the San Francisco Giants for RHP Jordan Hicks, LHP Kyle Harrison, RHP Jose Bello and outfielder James Tibbs III. Hicks has already been traded to the Chicago White Sox, while Kyle Harrison was flipped to the Milwaukee Brewers in the deal that netted Boston their starting third baseman for 2026, Caleb Durbin. Neither Bello or Tibbs is seen as a particularly impactful prospect.
To make matters worse, the Red Sox alienated Devers by moving him off of third base in favor of Bregman. However, Bregman opted out of his contract after just one season in Boston, and departed for a lucrative five-year deal with the Chicago Cubs this offseason. Devers probably needed to be moved off of third base, but angering him to the point you lose his bat only would have been worth it if you had a long-term impact replacement.
Devers is owed $226.5 million over the next eight seasons, which the Red Sox got out of in this trade. The thing is, this is a 29-year-old with an .855 career OPS. Even if Devers spends the rest of his career as a DH/1B, his bat makes him worth that price. The Red Sox would probably be World Series favorites in the American League if they had Devers slotted in to hit cleanup in Alex Cora's lineup in 2026.
Marlins Let Jesus Luzardo Burn a Hole in Their Pocket
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Why did the Miami Marlins feel compelled to trade Jesús Luzardo last offseason? It's fair to wonder that, considering he was coming off of a 2024 season where left elbow tightness and a lumbar stress reaction limited him to just 12 starts.
Perhaps president of baseball operations Peter Bendix feared that if Luzardo had another injury-riddled 2025 season, his trade value would completely plummet. Clearly, though, he would have been better off finding out.
Luzardo went 15-7 with a 3.92 ERA, 2.90 FIP and 216 strikeouts across 183.2 innings in his first season with the division-rival Phillies. He finished seventh in NL Cy Young Award voting in 2025, and there's even higher hopes for what the 28-year-old could do in his contract year of 2026.
Now, we're not being naive here. The Phillies may make the long-term investment necessarry to keep Luzardo beyond 2026. Nothing about the history of the Marlins suggests they would have. Still, if they had held onto Luzardo for just the first half of 2025, he would have been coveted before last July's trade deadline. If not, the Fish could have flipped Luzardo this winter, like they did with Edward Cabrera.
Instead, they traded him in December of 2024 for pennies on the dollar, getting back two prospects in return for him and minor-league catcher Paul McIntosh: shortstop Starlyn Caba and outfielder Emaarion Boyd. Caba is a glove-first shortstop that was the main piece Miami got in the trade. He's still only 20 years old, but while Luzardo had a huge year for the Phillies, Caba hit just .222 in 51 games at Single-A Jupiter.
Mets Trade Pete Crow-Armstrong for Half a Season of Javier Báez
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After Pete Crow-Armstrong hit just .216 with a .634 OPS after the All-Star Break last season, the jury remains out exactly what PCA is as an offensive player.
Despite that disappointing second half at the plate, Crow-Armstrong still finished eighth in NL MVP voting as a 23-year-old. That's in part because he homered 31 times, drove in 95 runs and stole 35 bases.
But the largest chunk of Crow-Armstrong's value comes in him being arguably the best defender at any position in baseball, as he won a Gold Glove Award in center field last season with 15 defensive runs saved and 21 outs above average at a premium position.
Crow-Armstrong—who can't become a free agent until after the 2030 season—was traded by the Mets for half a season of Javier Báez in July of 2021. (The Mets did also acquire RHP Trevor Williams in the trade.) Báez actually did post an .886 OPS as a Met, but New York crashed and burned after the trade, finishing the season at 77-85. The Mets let Báez walk for a six-year, $140 million deal with the Detroit Tigers, which has proven to be a smart move. However, it makes giving up Crow-Armstrong a year after he was their first-round pick even more perplexing. Imagine if they had him in center field right now.
Instead, the Mets are rolling the dice on Luis Robert Jr. in 2026, hoping that this is the year the former All-Star is finally able to stay healthy.
Red Sox Deal Chris Sale Before Cy Young Season
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When Chaim Bloom and the Red Sox traded Chris Sale and cash considerations to the Atlanta Braves for Vaughn Grissom in December of 2023, there was definitely logic in it.
Sale pitched just 151 total innings between 2020 and 2023, leaving you with the impression that someone who was once one of the greatest starters in the sport wouldn't stay healthy enough to be a frontline pitcher again.
Additionally, while there were defensive concerns with Grissom, he had impressed enough to make his MLB Debut as a 21-year-old in 2022. He hadn't shown much in his early time in the majors, but Grissom seemed like a strong change-of-scenery candidate.
But while there was logic at the time of the deal, it's turned into a disaster for the Red Sox.
Sale won the NL Cy Young Award in 2024, his first season with the Braves. He's been an All-Star twice in as many seasons in Atlanta, and while he was limited to 125.2 innings in 2025, the 2.46 ERA he has in 303.1 innings with the Braves means he's regained his place as one of the game's elite starters.
Meanwhile, Grissom played in only 31 games with the Red Sox, hitting .190 with a miserable .465 OPS in 2024. After spending his entire 2025 season at Triple-A Worcester, the Red Sox traded Grissom to the Los Angeles Angels in December.
It's entirely possible that 2026 will be the final season of Sale's career, which might be destined for the Hall of Fame after what he's done during his first two seasons in Atlanta. If there's any consolation, Sale's Cooperstown plaque will probably still have a Red Sox cap on it.
Twins Trade Future All-Star Closer for … Basically Nothing
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It often takes relief pitchers multiples stops to really figure things out, and Trevor Megill is a great example of that.
When the Minnesota Twins designated Megill for assignment in April of 2023, he had a 6.03 ERA in 67 career relief appearances between the Cubs and Twins. There was no indication the Twins would regret trading him to the Milwaukee Brewers for a player to be named later or cash considerations.
However, in parts of three seasons since being acquired by the Crew, Megill has a 2.88 ERA and 2.62 FIP across 129 games. During that period, he's thrived as both a set-up man and a closer. He was an All-Star in 2025 for a Brewers team that led baseball in wins, as he recorded 30 saves in 50 appearances. While he's 32 years old, he still won't be eligible for free agency until after the 2027 season.
We'll wait to see how the returns that the Twins got for Jhoan Duran, Griffin Jax and Louis Varland last summer pan out. There's been enough time in this case, though, to conclude that the Twins would like a mulligan on Megill.
Dodgers Give Up Young Oneil Cruz
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The Dodgers have so much financial might that the rare mistakes they make don't burn them nearly as much as they would for lower-budget clubs. Also, to be clear, future Hall of Fame executive Andrew Friedman doesn't miss very often.
However, relatively early in his time on the job in Los Angeles, Friedman traded Cruz and Angel German to the Pirates for left-handed reliever Tony Watson at the 2017 trade deadline. Watson did post a 2.70 ERA in 24 games for the Dodgers after the trade, and then was a postseason workhorse for a team that pushed the Houston Astros to seven games in the World Series.
But Watson departed for a multi-year deal with the Giants after the 2017 season. He last pitched in the majors in 2021. Meanwhile, Cruz perhaps still hasn't reached his full potential, but he led the NL with 38 stolen bases in 2025. He's also posted a .795 OPS against right-handed pitching in his career. Perhaps if he was in Los Angeles, his full potential would have been unlocked by now, although this version of the 27-year-old is still very useful.
Oh well, Friedman can cry onto the three World Series trophies he's won since trading Cruz away for a rental reliever. You can't win 'em all.
Rays Trade Future Ace During Roster Crunch
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People use to say that if the Rays are interested in someone on your roster, you don't want to trade that player, because you're probably missing something that Tampa Bay will tap into.
However, former Phillies general manager Matt Klentak struck gold on a trade with the Rays in November of 2019. With the Rays needing to add Cristopher Sánchez to the 40-man roster or risk losing him in the Rule-5 Draft, the Phillies swooped in and traded infield prospect Curtis Mead for the lanky lefty.
It took a few years for Sánchez to look like much more than a fringe major leaguer, but boy has he come on. Since the start of the 2024 season, Sánchez's 11.1 WAR is second only to Tarik Skubal, per FanGraphs. He was an All-Star in 2024, and then finished runner-up to Paul Skenes in NL Cy Young Award voting in 2025.
Meanwhile, Mead hit just .238 with a .629 OPS in parts of three seasons with the Rays from 2023 to 2025, before being traded to the White Sox last summer as part of the deal that brought Adrian Houser to Tampa Bay.
Sánchez, still only 29, is one of the consensus top five pitchers in baseball entering the 2026 season.
