The Top 10 Contract Years to Watch in 2026: Unlocking Massive Deals or Bust?
The upcoming season promises to be a pivotal year for many players as they approach the end of their contracts, with potential mega-deals on the horizon.
As we embark on the 2026 season, the spotlight shines on those players entering their contract years, a crucial period that can significantly impact their careers and earnings. While teams assess a player's entire career during contract negotiations, the final season before free agency can be a make-or-break moment.
Here's a deep dive into the top 10 players with intriguing contract years, ranked by their 2025 FanGraphs WAR:
Skubal's Historic Chase: Skubal's journey this season is one to watch. He aims to join the elite club of Greg Maddux and Randy Johnson as the only pitchers with three consecutive Cy Young Awards. A remarkable feat, but there's more. With another dominant season, Skubal, at 29, could surpass Yoshinobu Yamamoto's record-breaking $325 million contract, the richest ever for a pitcher. Will he cement his legacy and break the bank?
Luzardo's Redemption: Despite a 3.92 ERA in 2025, Luzardo's true potential was masked by a rough patch. His 2.90 FIP tells a different story, indicating a stellar season for the Phillies' lefty. After a strong comeback from an injury-plagued 2024, he struck out 216 batters in a career-high 183 2/3 innings. But here's the catch: Luzardo's injury history might be a concern for teams. With only two seasons of 18+ starts, can he prove his durability and become a free-agent darling?
Chisholm's Star Potential: In a free-agent class lacking star power, Chisholm can shine. His 2025 season was impressive, achieving a rare 30-30 season for the Yankees. But there's a twist: Chisholm is relatively young, turning 28 next offseason. Can he replicate his success and become the face of a weak free-agent class?
Pivetta's Payoff: Last offseason, Pivetta's $55 million deal with the Padres raised eyebrows, given his ERA history. But he silenced critics with a career year, posting a 2.87 ERA and 190 K's. With an opt-out clause in 2026, Pivetta could secure an even bigger payday if he maintains this form.
Peralta's Consistency: Dylan Cease's massive deal with the Blue Jays set a precedent for durable strikeout artists. This bodes well for Peralta, who aims for his fourth straight season with 30+ starts and 200+ strikeouts. Interestingly, Peralta's ERA has been more consistent than Cease's in recent years. And this is the part most people miss: Peralta's reliability could make him a hot commodity.
Sale's Late-Career Gamble: Chris Sale, surprisingly, has never been a free agent, thanks to a series of extensions. But at 37, he's approaching uncharted territory. The Max Scherzer-Mets deal at a similar age sets a precedent. Can Sale, coming off a strong 2024 and an injury-filled 2025, continue his late-career magic and command a massive contract?
Rogers' Redemption Arc: The past five years have been a rollercoaster for Rogers. Was his 2021 and 2025 success a fluke, or are his 2022-24 numbers more indicative of his true ability? His contract year will be a telling tale.
Grisham's Breakout: Grisham's 2025 season was a revelation, hitting 34 home runs and posting a 125 OPS+. But his free agency was complicated by draft compensation penalties. He accepted the Yankees' qualifying offer, and now he aims to prove his worth again.
Arozarena's Bat Power: Arozarena, like Chisholm, stands out in a free-agent class lacking impact hitters. With five straight 20-20 seasons and a solid OPS+, he's a force to be reckoned with. But a high strikeout rate and Seattle's pitcher-friendly park might be hurdles. Can he overcome these challenges and land a massive deal?
King's Injury Comeback: King's 2025 was cut short by injuries, but his 2024 performance proved his starter potential. With draft compensation attached, his free agency was affected. Now, a healthy 2026 could be his ticket to a bigger contract without the QO constraints.
Other Notable Contract Years: Sandy Alcantara (club option), Shane Bieber, Jack Flaherty, Kevin Gausman, Sonny Gray (club option), Shota Imanaga, Casey Mize, Robbie Ray, Brandon Woodruff, Ian Happ, Luis Robert Jr. (club option), George Springer, Seiya Suzuki, Daulton Varsho, Taylor Ward, Nico Hoerner, Gleyber Torres, Max Muncy, Ha-Seong Kim, Bryan Abreu, David Bednar, Ryan Helsley (opt-out), and Pete Fairbanks.
As these players navigate their contract years, the baseball world eagerly awaits their performances. Will they rise to the occasion and secure their place in history and on the payroll? Only time will tell. But one thing is certain: the 2026 season will be a pivotal year for these athletes, with potential controversy and massive deals on the line.
