As MLB teams prepare for the offseason, the impending free agency of players like Juan Soto will have organizations feeling optimistic about potential long-term contracts. Soto, at 26 years of age, is expected to sign a deal extending close to 15 years. Given his elite offensive skills, there is a general consensus that any contract he signs will age favorably, even if his primary position changes during that time. While inherent risks always accompany such large contracts, including the potential for significant injuries, Soto represents one of the more secure investments in terms of talent longevity among this year’s free agents. Comparatively, other high-profile players may carry a greater risk, given their injury histories or inconsistent performances leading up to free agency.

Alex Bregman of the Houston Astros is projected to seek a deal resembling the 11-year, $350 million extension signed by Manny Machado with the San Diego Padres ahead of the 2023 season. This raises questions regarding not only Bregman’s past performance but also the long-term viability of such lucrative contracts. In comparing their performances from 2020 to 2022, Machado posted a .291 batting average with a .881 OPS, generating 14.2 Wins Above Replacement (WAR), while Bregman’s numbers during the same timeframe—.260 batting average, .798 OPS, and 14.0 WAR—suggest a marked difference in production during a critical period for contract negotiations. A major consideration for teams will be whether that potential salary is justified based on Bregman’s trajectory as he approaches free agency.

As for Jack Flaherty, he recently demonstrated his ability as a solid pitcher with a 3.17 ERA across 162 innings, playing for both the Detroit Tigers and Los Angeles Dodgers. However, a lack of consistency over the previous four seasons presents a concern for potential suitors. Flaherty logged a disappointing 4.99 ERA, following an impressive 2019 season where he finished fourth in NL Cy Young voting. Consequently, MLB insiders predict he may land a three-year, $60 million deal, but teams must weigh the risk of investing heavily in a pitcher who has struggled for several seasons. Should he return to form, as seen in 2019 or 2024, he would certainly offer terrific value.

Max Scherzer, widely regarded as one of the premier pitchers in MLB history and a three-time AL Cy Young Award winner, might command a one-year contract of $16 million this offseason. However, concerns linger regarding his health after an offseason back surgery delayed his debut in 2024. Given his age—turning 41 during the upcoming season and with over 2,878 career innings pitched—there's growing speculation that his durability may not hold up. If Scherzer plays to his past standards, he could provide profound benefits; however, a repeat of the injuries from the previous season would pose significant financial liability for any team willing to invest.

Another intriguing player is Nick Pivetta, who has shown promise throughout his career. Following a season where he posted a 4.09 ERA over the last two years, Pivetta's potential earned him a one-year, $21.05 million qualifying offer from the Red Sox, which he subsequently declined. This leaves teams looking at him in free agency wondering if they can capture the best version of Pivetta, as he approaches his age-32 season.

Anthony Santander of the Baltimore Orioles presents a unique situation as well. With a monster 2024 campaign that featured 44 home runs and 102 RBIs, projecting his future performance becomes challenging. Consistency in terms of power output is essential, and while forecasts suggest a five-year, $101 million contract might be on the horizon, the margin for error is narrow due to his previous performance variations.

Justin Verlander is another veteran player attracting attention this offseason, despite being left off the AL Wild Card Series roster following a lackluster regular season performance, including a 5.48 ERA across 17 starts. His past accolades, including being a three-time AL Cy Young winner, make him an attractive option for teams willing to take a gamble on a one-year deal, despite his 42nd birthday approaching. Unlike younger players, investing in Verlander carries the weight of how quickly he could age and the effectiveness of his performance on the mound in 2025.

Walker Buehler's journey back from injury has raised concerns regarding his ability to recapture his former Cy Young-caliber pitching. While he contributed to the Dodgers' World Series success, his regular season numbers, including a 5.38 ERA, create uncertainty about what a team would get should they sign him for a more extended period. Most projections suggest that a one-year deal would likely be sufficient as a trial period, with future contract implications hinging on performance and health.

Finally, Jurickson Profar's dramatic fluctuations in performance make him a wild card entering free agency. His transition from an uninspiring 2023 season to an All-Star 2024 suggests both his upside and potential downside are considerable, hovering between two extremes in various contexts. Depending on how his performance is perceived, Profar could see a modest contract offer or a more substantial deal, representing the dichotomy facing many teams as they consider the financial ramifications of pursuing free agents coming off unpredictable seasons.

In summary, various MLB players heading into free agency this winter may represent both significant risks and opportunities for teams willing to roll the dice. Close evaluations from teams' front offices will be crucial in determining which players are worth the investment versus those who may ultimately prove to be overpays over the duration of their contracts.