The Mookie Betts deal and the 15 worst MLB trades of the past decade

Mookie Betts added to his legend this week when he made his return to the Los Angeles Dodgers lineup, hitting a home run in his first game back after missing two months due to a hand fracture.

While moments like that are what many baseball fans have come to expect from Betts over the years, it further solidified his status as one of the greatest players in recent memory. It also led FOX Sports’ Colin Cowherd to make a pretty big proclamation.

“The two worst trades in major league baseball history both belong to the Red Sox,” Cowherd said. “They gave up Babe Ruth, and they gave up Mookie Betts.

“You think I’m being hyperbolic here, Mookie Betts had been gone for two months. The kid’s incredible. When he was in his prime, the Red Sox were like, ‘We’re going to move him to the Dodgers.’ Yeah, you’ll need a search party for the guys they got for him because only one player still remains with the Red Sox.”

When the Red Sox traded Betts in February 2020, he was entering the final year of his contract. As Boston failed to get him to agree to a long-term deal, some thought he might have been bound for free agency.

However, Betts signed a 12-year, $365 million deal with the Dodgers in July 2020. Three months later, the Dodgers won the World Series, with Betts playing a key role.

Meanwhile, the Red Sox haven’t achieved the highs that they reached with Betts, who won AL MVP in 2018 and helped them win the World Series that same year. Boston ranks 17th in winning percentage, 17th in run differential and 18th in home run differential since the 2020 trade.

On a note that might scare Red Sox fans, the Betts trade came exactly 100 offseasons after they traded Ruth. Of course, it’s too early to tell if an 86-year title drought will come from the Betts deal. But it’s already evident that it’s among the worst in MLB history.

Let’s look at some of the worst trades of the last decade. 

Braves get Max Fried as part of haul for Justin Upton (2015 offseason)

Braves received: Max Fried, Jace Peterson, Dustin Peterson, Mallex Smith
Padres received: Justin Upton and Aaron Northcraft

The Braves hit big on their return in the Upton trade, selling high after his strong season and a year before he became a free agent. Fried, who was one of the best pitching prospects in baseball at the time of the trade, was four months removed from Tommy John surgery.

As a result, Atlanta didn’t fully reap the rewards of the deal for quite some time. Fried was called up in 2017, but didn’t become a full-time starter for the big league team until 2019. He’s been one of the best pitchers in baseball since, earning two All-Star nods and two top-five Cy Young finishes. He was also the ace of the Braves’ 2021 World Series rotation.

Upton had an All-Star season with the Padres in 2015. But he was only in San Diego for one year, signing a six-year, $132.75 million deal with the Detroit Tigers in the ensuing offseason. 

Blue Jays received: Josh Donaldson
Athletics received: Brett Lawrie, Kendall Graveman, Sean Nolin, and Franklin Barreto

The Athletics decided to move off their best hitter even though he was cost-controlled and helped them make the playoffs for a third-straight season. 

Donaldson almost instantly made this one of the worst trades in recent memory. He hit 40 homers in his first season with the Blue Jays, winning AL MVP in 2015. He remained one of the best hitters in the American League for the next couple of seasons, combining with a pair of playoff berths as Toronto had its best run since its title-winning seasons in the early 1990s. 

Meanwhile, the A’s traded Lawrie after one season, while Graveman had a few OK, but unspectacular, seasons in Oakland. 

Marlins received: Luis Castillo, Kendry Flores
Giants received: Casey McGehee

There might be a few trades involving Castillo that could make this list. Let’s go with the one that started it all. 

The Giants dumped Castillo for McGehee to replace third baseman Pablo Sandoval. McGehee didn’t last two full months in San Francisco, getting designated for assignment after hitting .213 with a .575 OPS with the Giants. 

Meanwhile, Castillo remained in the Marlins’ system for a couple of seasons. He was actually traded to the Padres in 2016, but was sent back to the Marlins when Colin Rea was injured in his first start with Miami. The Marlins traded Castillo to the Reds in the following offseason as part of a package for Dan Straily, who at least pitched in Miami for two seasons.

Braves acquire Dansby Swanson in haul for former star pitcher (2016 offseason)

Braves received: Dansby Swanson, Ender Inciarte, Aaron Blair
Diamondbacks received: Shelby Miller and Gabe Speier

In the offseason after getting Fried, the Braves landed another top prospect who helped kick-start their recent run as perennial contenders in the National League. 

Just six months after he was the No. 1 pick in the 2015 MLB Draft, Swanson was the main piece to be moved for Miller, who was coming off an All-Star season. Miller struggled in Arizona, posting a 6.15 ERA in 2016 before missing the majority of the 2017 and 2018 seasons due to Tommy John surgery.

Swanson became the Braves’ everyday shortstop within a year of the trade, becoming one of the best shortstops in baseball by 2020. As Swanson hit a pair of big homers in the Braves’ 2021 World Series win, Inciarte was an All-Star in 2017, tipping the scales even further for Atlanta. 

Padres received: Fernando Tatis Jr.
White Sox received: James Shields

This trade might be one of the most lopsided one-for-one deals in MLB history. The White Sox looked to bolster their rotation, giving up a 17-year-old Tatis who’d yet to play a game in their system, for Shields, a decorated veteran. 

Shields’ best days were past him, though, when he arrived in Chicago’s South Side. He had a 6.77 ERA in his first year with the White Sox before posting a 5.31 ERA over his three-plus years with the team. 

As for Tatis, he’s only become one of the best hitters in baseball since his call-up in 2019. He’s already a two-time Silver Slugger winner at 25 and is poised to be one of the best players in baseball over the next decade.  

Astros receive Yordan Álvarez in trade for reliever (2016 trade deadline)

Astros received: Yordan Alvarez
Dodgers received: Josh Fields

Andrew Friedman has rarely missed over his two decades as a lead baseball executive. But he missed in a big way when he traded for Fields, an ordinary reliever, in the middle of the 2016 season. He gave up Alvarez, who was 19 at the time and had yet to play in a Major League game. Alvarez quickly rose through the Astros’ system and was called up in the 2019 season, instantly turning into one of the best sluggers in the league. 

Friedman expressed regret over the trade during Alvarez’s torrent rookie season. 

“Looking back on it now, we obviously wish we would have said yes to other names they asked for before him,” Friedman told reporters. “It’s pretty special watching what he’s doing in the batter’s box.”

White Sox received: Eloy Jiménez, Dylan Cease, Matt Rose, and Bryant Flete
Cubs received: Jose Quintana

As the Cubs were desperate to get pitching help in their quest to try and repeat in 2017, they wound up helping their crosstown rivals in a big way. 

Jiménez and Cease played big roles in the White Sox’ brief success earlier in the decade, with the former winning a Silver Slugger Award in 2020. Cease was one of the top young pitchers at the time and has developed into one of the top pitchers in the game.

While the White Sox didn’t achieve great success with Jiménez and Cease, they were at least able to move them for prospects in recent months. As for the Cubs, Quintana had a few OK-ish seasons, but didn’t help the team even come close to winning a title.

Marlins land two standout pitchers for Marcell Ozuna (2018 offseason)

Marlins received: Sandy Alcántara, Zac Gallen, Magneuris Sierra, Daniel Castano
Cardinals received: Marcell Ozuna

Miami went on a fire sale during the 2018 offseason, but one of the trades netted it a pair of future All-Star pitchers. It got Alcántara, a two-time All-Star who won the NL Cy Young in 2022, and Gallen. The Marlins didn’t get to enjoy Gallen’s All-Star emergence, trading him to the Arizona Diamondbacks at the deadline in 2019. However, they got Jazz Chisholm as part of that deal.

Ozuna has been on a tear with the Braves this season, but the Cardinals didn’t get to enjoy him for too long. After two solid seasons at the plate, Ozuna left St. Louis in free agency ahead of the 2020 season. 

Brewers received: Christian Yelich
Marlins received: Lewis Brinson, Isan Díaz, Monte Harrison, and Jordan Yamamoto

One of the other trades the Marlins made in their fire sale immediately blew up in their face. Yelich won NL MVP in his first season in Milwaukee and was the runner-up in 2019. 

Yelich’s hitting took a dip between the 2020-23 seasons as he dealt with lingering back issues. Still, Yelich was able to regain his All-Star form this season, and the four players the Marlins received in the deal aren’t even in the majors. 

Rays get haul for Chris Archer (2018 deadline)

Rays received: Tyler Glasnow, Austin Meadows, Shane Baz
Pirates received: Chris Archer

When the Pirates traded for Archer in 2018, they thought they were getting a pitcher who’d help them make a playoff push and be the ace of their rotation for years to come. 

Instead, they got a pitcher who went 6-12 with a 4.92 ERA in his year-plus with the ballclub. Oh, and they also gave up two future All-Stars and a promising pitcher. Glasnow and Meadows have since moved on from Tampa, but both had much better stints with the Rays than Archer did with the Pirates. Baz is finally back up in the majors and starting again after missing over a year due to Tommy John surgery. He was also initially a player to be named later in the trade. 

Guardians received: Emmanuel Clase, Delino Deshields Jr.
Rangers received: Corey Kluber, cash considerations

The Rangers gave up a future All-Star closer for one inning of Kluber. Kluber, a two-time Cy Young winner, suffered a torn teres major muscle in the first inning of his only start with Texas, missing the rest of the 2020 season with the injury before leaving in free agency. 

Clase missed the entire 2020 season due to a suspension for performance-enhancing drugs. But he’s been one of the game’s best relievers since he made his debut with the Guardians in 2021, being named an All-Star in each of the last three seasons and has 147 saves since 2021. 

Rangers acquire key title piece in Adolis García (2020 offseason)

Rangers received: Adolis García
Cardinals received: Cash considerations

While the Kluber deal was a disaster for the Rangers, another deal they made in the same month was one of the reasons why they won the World Series in 2023. 

Texas landed García for cash considerations after St. Louis designated him for assignment during the 2020 offseason. García, who was 26 at the time of the move, had struggled to break through and become an everyday player with the Cardinals. He only had six at-bats in the 2020 season before becoming an All-Star in 2021. He was an All-Star again in 2023 and later a postseason hero, winning ALCS MVP. 

Rays’ acquire postseason hero Randy Arozarena (2020 offseason)

Rays received: Randy Arozarena, Jose Martinez
Cardinals received: Matthew Liberatore

García wasn’t the only outfielder that the Cardinals gave up in the 2020 offseason who went on to be a postseason hero.

Arozarena was moved by St. Louis after a brief stint in the majors, traded as the Cardinals sought to improve their minor-league pitching. The trade aged poorly in less than a year, though. Arozarena was a catalyst for the Rays’ World Series run in 2020 before winning AL Rookie of the Year in 2021 and being named an All-Star in 2023.

As for Liberatore, he’s settled in with the Cardinals as a reliever after struggling in a starting role.

Dodgers trade for Mookie Betts (2020 offseason)

Dodgers received: Mookie Betts, David Price
Red Sox received: Alex Verdugo, Jeter Downs, Connor Wong

As Cowherd mentioned, this might be the second-worst trade in MLB history.

The Red Sox gave up Betts before he entered the final season of his contract, using the deal to also get half of Price’s remaining salary off the books. The deal was immediately panned as the Red Sox gave up a then 27-year-old superstar who had led them to a World Series title and was only a year removed from winning MVP.

Somehow, the deal has continued to age poorly. Betts led the Dodgers to a World Series win in 2020 and has remained one of the best players in baseball since the time of the trade. Meanwhile, two of the three players the Red Sox got in the deal are already out of Boston, with Downs failing to reach his potential as a prospect. Wong has had a solid season at the plate in 2024, but if the best player you get for a perennial MVP candidate is a catcher who doesn’t start every day, then you automatically enter this list.

Royals received: Cole Ragans, Roni Cabrera
Rangers received: Aroldis Chapman

Rangers fans could wipe away this move by saying that they won the World Series in 2023 and that banners fly forever. Chapman had some solid numbers in the postseason as well (2.25 ERA over nine appearances), giving some extra credence to that claim. 

However, giving up a 25-year-old starting pitcher who became an All-Star a year after the trade is a pretty tough pill to swallow, especially for a Rangers squad whose rotation largely consists of pitchers in their 30s.

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