MLB’s 6 riskiest contracts of the offseason feature Alex Bregman prominently, as his recent signing with the Boston Red Sox raises eyebrows. The hot stove season has wrapped up, with many top players now off the market. Free agency inherently carries risks for both teams and players, as those in charge must balance the potential for high rewards against the fear of being tied to a burdensome contract. For executives and superstars alike, the stakes are high, and the consequences of miscalculations can haunt them for years.
However, with risk comes the chance for significant rewards and opportunities. Teams willing to take bold steps deserve recognition for their efforts to enhance their rosters, even if the outcomes remain uncertain. This season’s high-profile moves are sure to shape the future of Major League Baseball.
Examining the six riskiest contracts of the offseason reveals the complexities involved. The Oakland Athletics made a notable gamble when they secured a middle-of-the-rotation starter, Luis Severino, to the largest contract in franchise history despite his injury history. While this move may have been necessary to attract a veteran arm to a struggling organization, it raises questions about their financial strategy, especially when the second-highest salary on the A’s 2025 payroll is a mere $10.5 million for Jeffrey Springs.
Spending $22 million annually over three years on a starter with durability concerns is a risky proposition. Severino, who previously struggled with injuries—including Tommy John surgery—has shown signs of improvement, throwing 182 innings last season. Yet, his mediocre 3.91 ERA and below-average strikeout rate indicate that he may not return to his former ace status.
The San Francisco Giants also face uncertainty with Willy Adames, who will play in the home-run suppressing Oracle Park for the next seven years. After a career year with 32 home runs in 2024, concerns linger about whether Adames has peaked. His previous season’s struggles, including a .217 batting average, raise alarms about his consistency. Although he has been reliable in avoiding significant injuries and is recognized for his leadership, the $28 million average annual value makes this contract precarious.
The Atlanta Braves’ Max Fried also exemplifies the risks associated with long-term contracts for pitchers. His recent forearm injuries and the lengthy eight-year duration of his deal with the New York Yankees could lead to complications. Fried’s injury history, combined with the Yankees’ strategy of stacking their rotation, places immense pressure on him to perform consistently.
The Boston Red Sox’s decision to sign Alex Bregman for $40 million per year has generated excitement among fans eager to see a big-market team make a splash. However, Bregman, who can opt out after each season, must maintain his performance levels to justify the investment. His strong offensive stats at Fenway Park could mitigate concerns about his declining on-base percentage since 2019. Still, if his numbers falter, the Red Sox risk being locked into a hefty contract for 2026 and 2027.
Another consideration for the Red Sox is Bregman’s potential shift to second base, which could hinder the development of top prospect Kristian Campbell. With Rafael Devers struggling defensively at third base, the team faces tough decisions about positioning and player development moving forward.
The Los Angeles Dodgers also made headlines by securing the most sought-after free-agent reliever, Scott, for a record-setting contract. His $18 million average annual salary places him among the highest-paid relievers in baseball history, but the pressure to deliver on such a significant investment is palpable.
1. Juan Soto, Mets: 15 years, $765 million
The New York Mets’ signing of Juan Soto stands out as a monumental risk. At 26 years old, Soto must avoid serious injuries, but his impressive track record of playing 150 games in each of the last five seasons offers some reassurance. The financial burden of Soto’s $51 million annual salary complicates the Mets’ strategy, especially with other players like Pete Alonso seeking long-term deals. However, Soto’s exceptional hitting ability may ultimately justify the risks associated with this historic contract.
As the offseason progresses, the implications of these contracts will unfold, and teams will hope their high-stakes decisions pay off in the long run.
