MLB Free Agency 2026-27: Top Questions and Predictions (2026)

As we approach the midpoint of the 2026 MLB season, it's time to shift our focus to the upcoming offseason and the intriguing questions surrounding free agency. This year's free agency period promises to be an exciting and complex affair, with several factors coming into play that will shape the future of the league.

The Tarik Skubal Conundrum

One of the most intriguing storylines involves Tarik Skubal, who has undergone multiple elbow surgeries, including Tommy John surgery in college and a recent procedure to remove loose bodies from his left elbow. Despite these setbacks, Skubal's potential payday remains a hot topic among industry insiders. The average projection for his contract, based on a straw poll, is an impressive $357 million over 7.7 years, which would surpass Max Scherzer's record for average annual value. However, the question remains: will teams be willing to commit to such a deal given Skubal's durability concerns?

Labor Negotiations and the Potential Work Stoppage

The looming labor negotiations and the possibility of another lockout are sure to impact free agency. Teams often want to make their big spending moves before the current CBA expires, both to avoid delays and to signal their commitment to player spending. However, with the assumption that a lockout is likely, the question becomes: which teams and players will be willing to take the risk and sign before the deadline? The potential for a rushed posting process and the impact on the Korean and Japanese leagues further adds to the complexity of this offseason.

Who's the Top Position Player?

When it comes to position players, there is no clear front-runner. In the infield, names like Jazz Chisholm Jr., J.P. Crawford, and Brandon Lowe are in the mix, while the outfield features a group of similar players, including Daulton Varsho and Seiya Suzuki. The lack of high-end position players available in free agency is expected to drive more activity in the trade market, especially after the anticipated lockout.

Starting Pitching Depth

One area where the 2026-27 free agent market excels is starting pitching. Behind Skubal and Freddy Peralta, there is a deep pool of talented pitchers, including Trevor Rogers, Kevin Gausman, and Zac Gallen. This depth could provide teams with an opportunity to upgrade their rotations and compete for a championship.

The Mets and Cubs: A Tale of Two Teams

The New York Mets and Chicago Cubs find themselves in contrasting situations. The Mets, despite having the second-highest payroll in baseball, are struggling with the worst record. With over $71 million coming off the books and the potential opt-out of Bo Bichette's $42 million salary, the Mets have the opportunity to reshape their roster and make some much-needed upgrades. On the other hand, the Cubs, with one of the best records in baseball, face the challenge of replacing a significant portion of their rotation and outfield, as well as shoring up their bullpen.

Final Thoughts

This offseason promises to be a fascinating period of negotiation and strategy, with teams navigating the complexities of labor negotiations, player durability concerns, and the ever-changing market dynamics. As an avid baseball fan and analyst, I can't wait to see how these storylines unfold and shape the future of the MLB.

MLB Free Agency 2026-27: Top Questions and Predictions (2026)

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