The Mookie Betts deal stands as a pivotal moment in Major League Baseball history, particularly for the Boston Red Sox. This week, Betts made headlines once again by returning to the Los Angeles Dodgers lineup, marking his comeback with a home run after a two-month absence due to a hand fracture.
Such remarkable performances are what fans have come to expect from Betts, further cementing his legacy as one of the greatest players of his generation. FOX Sports commentator Colin Cowherd made a bold statement regarding the Red Sox’s decision to trade Betts, claiming, “The two worst trades in Major League Baseball history both belong to the Red Sox. They gave up Babe Ruth, and they gave up Mookie Betts.”
Cowherd emphasized the absurdity of the trade, noting, “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.” This statement underscores the profound impact Betts has had on the Dodgers and the regret that lingers in Boston.
In February 2020, the Red Sox traded Betts as he entered the final year of his contract, unable to secure a long-term deal. Many speculated he would hit free agency, but he ultimately signed a staggering 12-year, $365 million contract with the Dodgers in July 2020. Just three months later, Betts played a crucial role in leading the Dodgers to a World Series victory.
Since that trade, the Red Sox have struggled to replicate the success they enjoyed with Betts, who was named AL MVP in 2018 and contributed significantly to their World Series win that same year. In stark contrast, Boston now finds itself ranking 17th in winning percentage and run differential, and 18th in home run differential since the trade.
Adding to the historical weight of this trade, it occurred 100 offseasons after the infamous Babe Ruth trade. While it remains to be seen if the Betts deal will extend an 86-year championship drought for the Red Sox, it is already recognized as one of the worst trades in MLB history.
In light of the Betts trade, let’s examine some of the other significant trades that have left fans and analysts scratching their heads over the past decade.
Braves acquire 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 capitalized on the Upton trade, acquiring Fried, a top pitching prospect recovering from surgery. Although Fried took time to develop, he emerged as a key player, contributing to the Braves’ 2021 World Series victory.
Blue Jays received: Josh Donaldson
Athletics received: Brett Lawrie, Kendall Graveman, Sean Nolin, and Franklin Barreto
The Athletics traded their best hitter, Donaldson, who went on to win the AL MVP in 2015 with the Blue Jays. In contrast, the players the A’s received failed to make a significant impact.
Marlins received: Luis Castillo, Kendry Flores
Giants received: Casey McGehee
The Giants traded for Castillo in a move that backfired, as McGehee struggled to perform and was quickly designated for assignment. Meanwhile, Castillo eventually found success in the Marlins’ system.
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
Swanson, a former No. 1 draft pick, became a cornerstone player for the Braves. In contrast, Miller struggled and underwent Tommy John surgery, diminishing his value.
Padres received: Fernando Tatis Jr.
White Sox received: James Shields
This trade is often cited as one of the most lopsided in MLB history. The White Sox traded a young Tatis, who has since become a superstar, for Shields, who did not deliver the expected performance.
Astros receive Yordan Álvarez in trade for reliever (2016 trade deadline)
Astros received: Yordan Alvarez
Dodgers received: Josh Fields
The Astros acquired Alvarez, who quickly became one of the league’s best hitters, while the Dodgers received a reliever who failed to make a significant impact.
White Sox received: Eloy Jiménez, Dylan Cease, Matt Rose, and Bryant Flete
Cubs received: Jose Quintana
The Cubs traded away key future stars in Jiménez and Cease for Quintana, who did not live up to expectations, leaving the White Sox with a significant advantage.
Marlins land two standout pitchers for Marcell Ozuna (2018 offseason)
Marlins received: Sandy Alcántara, Zac Gallen, Magneuris Sierra, Daniel Castano
Cardinals received: Marcell Ozuna
The Marlins acquired two future All-Stars in Alcántara and Gallen while the Cardinals traded away a player who left after two seasons.
Brewers received: Christian Yelich
Marlins received: Lewis Brinson, Isan Díaz, Monte Harrison, and Jordan Yamamoto
Yelich quickly became an MVP candidate with the Brewers, while the players received by the Marlins have struggled to make a significant impact.
Rays get haul for Chris Archer (2018 deadline)
Rays received: Tyler Glasnow, Austin Meadows, Shane Baz
Pirates received: Chris Archer
The Pirates traded for Archer, expecting him to be a top pitcher, but he struggled while the Rays gained two future stars in Glasnow and Meadows.
Guardians received: Emmanuel Clase, Delino Deshields Jr.
Rangers received: Corey Kluber, cash considerations
The Rangers traded for Kluber, who suffered a major injury, while Clase has emerged as one of the top closers in the game.
Rangers acquire key title piece in Adolis García (2020 offseason)
Rangers received: Adolis García
Cardinals received: Cash considerations
The Rangers acquired García for a minimal cost, leading to his emergence as an All-Star and postseason hero, showcasing the potential of low-risk trades.
Rays acquire postseason hero Randy Arozarena (2020 offseason)
Rays received: Randy Arozarena, Jose Martinez
Cardinals received: Matthew Liberatore
Arozarena became a key player for the Rays, helping them reach the World Series, while the Cardinals’ return did not yield the same success.
Dodgers trade for Mookie Betts (2020 offseason)
Dodgers received: Mookie Betts, David Price
Red Sox received: Alex Verdugo, Jeter Downs, Connor Wong
As Cowherd remarked, this trade may be one of the worst in MLB history. The Red Sox parted ways with Betts, a superstar who had led them to a championship, while the players they received have struggled to make an impact.
Royals received: Cole Ragans, Roni Cabrera
Rangers received: Aroldis Chapman
While the Rangers celebrated a World Series victory, the loss of Ragans, who became an All-Star, may haunt them in the future.
The Mookie Betts trade and these other significant trades highlight the complexities and potential pitfalls of player transactions in Major League Baseball. As teams weigh the risks and rewards, the long-term implications of such deals often unfold in unpredictable ways.
