Boston Red Sox have long been known for their willingness to spend big on star players, but in recent years, two of their high-profile contracts have come under heavy scrutiny. As MLB analysts continue to assess the most burdensome deals in the American League (AL), two Red Sox names consistently make the list: Chris Sale and Trevor Story. These contracts, once thought to be investments in elite talent, are now considered among the worst in the league due to underperformance, injuries, and long-term financial. When the Red Sox extended ace Chris Sale in 2019 with a five-year, $145 million contract, it seemed like a no-brainer. Sale had been one of the most dominant pitchers in baseball, with a devastating slider and a track record of Cy Young-caliber performances. However, his tenure since signing the extension has been riddled with injuries. Sale missed the entire 2020 season following Tommy John surgery and has struggled to return to his pre-surgery form.
In the years since the surgery, Sale has been in and out of the rotation due to various injuries, failing to pitch a full season. With Boston paying $27.5 million annually for a pitcher who has barely been on the mound, the deal has become a major financial burden. The hope that Sale would return as the ace of the staff has faded, and his contract now limits the team’s ability to pursue other free agents or invest in player development.
**Trevor Story: The Uncertain Future**
Trevor Story’s six-year, $140 million deal, signed in 2022, was meant to solidify Boston’s infield following the departure of key players like Xander Bogaerts. The former Colorado Rockies star brought a strong defensive profile and consistent offensive production to the Red Sox, but injuries have derailed his time in Boston. Story missed a significant portion of the 2023 season due to elbow surgery, and questions about his durability have only grown.
In addition to his injury woes, Story has struggled to adjust to Fenway Park after playing most of his career at hitter-friendly Coors Field. His offensive numbers have dipped, and with four years remaining on his contract, Boston faces a difficult situation. The Red Sox are paying top-tier money for a player who has yet to live up to the expectations, and the team is unsure if he can regain his form.
**The Financial Fallout**
These contracts, when combined, put immense pressure on Boston’s payroll, hindering their flexibility to make competitive offseason moves. With Sale and Story locked into long-term deals, the Red Sox are financially tied to two players who have not provided the expected returns on investment. As other AL teams continue to grow stronger with strategic acquisitions, Boston’s roster limitations, tied to these contracts, are a cause for concern.
While both Sale and Story have the potential to bounce back, their current trajectory has placed them on the list of the worst contracts in the AL. If the Red Sox hope to regain their footing as perennial contenders, they will need either significant turnarounds from these two players or creative financial management to mitigate the impact of their bloated deals.
