The departure of Mookie Betts from the Boston Red Sox to the Los Angeles Dodgers in 2020 was a pivotal moment in Major League Baseball, sparking debate about the team’s future direction and the financial realities that shape player transactions. Former Red Sox executives have now suggested that Betts could have remained in Boston if the team had been willing to make different financial decisions, particularly involving deferred money in his contract. This revelation brings into question the financial strategies employed by both teams and offers insight into the broader dynamics of player movement in MLB.
Mookie Betts, one of the most talented and beloved players in Red Sox history, was traded to the Dodgers in February 2020, just one year before he was set to enter free agency. The trade, which sent Betts and pitcher David Price to Los Angeles in exchange for Alex Verdugo, Jeter Downs, and Connor Wong, was met with shock and disappointment by many fans in Boston. At the time, the Red Sox justified the trade as a financial move, arguing that they could not afford to commit the kind of money Betts would command on the open market, especially given their already high payroll.
However, former Red Sox executives have since indicated that the situation might have unfolded differently had the team been willing to offer deferred money in a potential extension with Betts, similar to what the Dodgers were willing to do. Deferrals in contracts are a common practice in MLB, particularly when teams need to manage their immediate financial obligations while still providing players with significant long-term compensation. The deferred payments would allow the team to pay the player over a more extended period, thus reducing the immediate financial burden.
The Dodgers, in contrast to the Red Sox, were willing to structure Betts’ deal in a way that would provide him with the massive payout he was seeking, while also allowing the team to manage their finances more flexibly over the years. Betts signed a 12-year, $365 million contract with Los Angeles in July 2020, just months after being traded. The deal included significant deferred payments, ensuring that Betts received his full compensation but over a longer period than a traditional contract might allow.
From the Red Sox’s perspective, executives have pointed out that had they been open to a similar structure, they could have retained Betts, allowing him to remain in Boston for the long haul. The Red Sox were at the time trying to reset their financials, which included avoiding a luxury tax threshold that would have placed additional strain on the team’s payroll. By offering deferred payments, the Red Sox could have made Betts’ contract more palatable in the short term, buying themselves time to work through their financial issues while keeping one of the best players in baseball.
However, it is important to note that while deferrals may have been a potential solution to retaining Betts, the broader question of whether the Red Sox truly valued him at the level of his worth remains central. The decision to trade Betts also highlighted the Red Sox’s reluctance to allocate vast sums of money to a single player, even one as generationally talented as Betts. The team’s front office at the time, led by Chief Baseball Officer Chaim Bloom, was focused on long-term financial flexibility and avoiding large, high-risk commitments to aging players, a strategy that ultimately led to the trade.
In contrast, the Dodgers, with their larger financial capacity and willingness to push the payroll limits, were able to commit to a player of Betts’ caliber. They could afford to add deferred payments into the equation, knowing that their deep-pocketed ownership group could weather the financial implications of such a deal.
Looking back, the trade of Mookie Betts remains a contentious issue in Boston, with many fans questioning whether the team made the right call. While the Red Sox may have been operating under the constraints of their financial model at the time, the situation underscores the complex relationship between financial flexibility and competitive success in professional sports. Had the Red Sox been more creative in their contract structure, such as incorporating deferrals, the outcome might have been different, and Betts might still be playing in Fenway Park today.
