In Major League Baseball (MLB), the issuance of substantial contracts during the free agency period carries inherent risks. As teams once again evaluate the market for its premier performers this winter, the weight of previous unwise long-term agreements looms large. Although many questionable deals have expired, such as Patrick Corbin's contract with the Washington Nationals, several notable contracts remain in play as they move toward the 2025 season. This analysis ranks the ten least favorable contracts that teams will continue to manage, focusing on players who have multiple years left on their agreements. Contracts with only a year remaining were excluded from this survey, as teams are typically better positioned to navigate those final seasons.

Factors such as remaining financial commitments, recent performances, and forecasts for future outputs were taken into consideration when compiling this ranking. Contracts with two years remaining were grouped together under the tenth position, as they present a less daunting prospect with a clear end in sight. The players occupying this category include: 3B Anthony Rendon of the Los Angeles Angels, $77.1 million; SP Robbie Ray of the San Francisco Giants, $50 million; OF George Springer of the Toronto Blue Jays, $48.3 million; OF Nick Castellanos of the Philadelphia Phillies, $40 million; SP Taijuan Walker of the Philadelphia Phillies, $36 million; SP Lance McCullers Jr. of the Houston Astros, $35.4 million; IF DJ LeMahieu of the New York Yankees, $30 million; and 1B/3B Jeimer Candelario of the Cincinnati Reds, $29 million. Among these, Rendon’s contract stands out as particularly burdensome, with only 4.7 Wins Above Replacement (WAR) accrued during the first five seasons of a seven-year, $245 million deal, making him one of the highest-paid players heading into 2025.

Further down the list, pitchers Walker and LeMahieu appear to be candidates for outright release, as their negative contributions may lead teams to reconsider their financial commitments. Conversely, if healthy, Robbie Ray could emerge as a key factor for the San Francisco Giants, while George Springer retains the potential to revert to his All-Star form with improved support. Andrew Benintendi, signed for five years and $75 million, has struggled significantly, posting a minus-0.8 WAR in his second season with the Chicago White Sox, compared to his prior All-Star accolade. Additionally, Christian Yelich, who once boasted MVP status, is now seen as a financial strain for the Milwaukee Brewers, having recently undergone back surgery after a resurgence. Meanwhile, Giancarlo Stanton’s postseason heroics were mitigate by his declining performance during the regular season, and Trevor Story’s struggles with injuries raise concerns for the Boston Red Sox as they look to the future.