Boston Red Sox, once known for their aggressive spending and ability to land superstar talent, are now facing scrutiny for some of the worst contracts in the American League (AL). Two of the most prominent names in the Red Sox lineup have found themselves on the list of bad contracts, a reflection of the team’s recent struggles to get value out of big-ticket signings while missing the playoffs for three consecutive seasons.
The first name on this list is pitcher Chris Sale, whose seven-year, $145 million extension signed in 2019 has become a source of frustration for the Red Sox and their fan base. When Sale first arrived in Boston in 2017, he was one of the most dominant pitchers in the game, leading the Red Sox to a World Series championship in 2018. However, since signing the extension, Sale has battled injuries, including Tommy John surgery, and has struggled to stay on the mound consistently. His inability to return to form, combined with his hefty price tag, has left many questioning the wisdom of the long-term commitment. The contract runs through 2025, and with Sale’s declining production and recurring health issues, it stands out as one of the most disappointing in the league.
The second name is outfielder and designated hitter Masataka Yoshida, whose five-year, $90 million deal has raised eyebrows since its signing in 2022. While Yoshida was brought in with high expectations after excelling in Japan’s Nippon Professional Baseball, his transition to Major League Baseball has been less than smooth. While he has shown flashes of power and on-base ability, his overall performance has not matched the lofty investment the Red Sox made. Critics argue that Yoshida has yet to justify the hefty contract, particularly as his defense and baserunning have also been below average, making him a liability in the field.
The inclusion of Sale and Yoshida on the list of worst contracts in the AL reflects a broader issue for the Red Sox: their financial mismanagement over recent years. Both contracts were signed with the hope of maintaining Boston’s status as a contender, but instead, they have weighed down the team’s payroll without delivering the expected results on the field As Boston continues to navigate a challenging financial landscape, the contracts of Chris Sale and Masataka Yoshida serve as cautionary tales of the risks that come with long-term, high-dollar deals. For the Red Sox to return to their former glory, they will need to make smarter investments moving forward, while finding a way to manage these burdensome deals that have become the face of their recent misfortunes.
