As the 2026 MLB season begins, several prominent players face crucial contract years that could shape their free-agent futures. Standouts include pitchers like Tarik Skubal and Chris Sale, alongside position players such as Jazz Chisholm Jr. and Trent Grisham, all aiming to build on recent performances.
The 2026 MLB season spotlights a group of players in their final contract years, where strong showings could lead to lucrative free-agent deals. Tarik Skubal of the Detroit Tigers, coming off a 6.6 fWAR in 2025, seeks a third consecutive Cy Young Award and aims to eclipse Yoshinobu Yamamoto’s $325 million pitcher contract record. At 29, the left-hander’s performance will draw intense scrutiny, whether he stays with Detroit or gets traded.
Jesús Luzardo, now with the Philadelphia Phillies after a trade from Miami, posted a 3.92 ERA in 2025 despite a tough stretch, backed by a 2.90 FIP over 183 2/3 innings with 216 strikeouts. The 28-year-old must prove durability, having topped 18 starts only twice in his career.
Among position players, New York Yankees’ Jazz Chisholm Jr. delivered a 30-30 season in 2025 with a 125 OPS+ despite an oblique injury, positioning the 28-year-old as a top free-agent target in a thin class. Teammate Trent Grisham rebounded dramatically, hitting 34 home runs with a 125 OPS+ in center field after accepting a $22.025 million qualifying offer.
Chris Sale of the Atlanta Braves, entering free agency at 37 for the first time, follows his 2024 Cy Young with a solid but injury-affected 2025 (3.6 fWAR). A deal akin to Max Scherzer’s 2021 $130 million pact could await if he sustains his renaissance.
Meanwhile, recent free-agent signings like Jack Flaherty (Tigers) and Anthony Santander (Blue Jays) eye rebounds after underwhelming 2025 campaigns. Flaherty, on a two-year deal, posted a 4.64 ERA last year after a strong 2024 split between Detroit and the Dodgers. Santander managed just six homers in 54 games due to injuries on his five-year, $92.5 million contract.
These narratives underscore the high stakes as teams evaluate talent for the open market.
