The 2026 Contract Year Countdown: Who Will Cash In and Who Will Crash Out?
The final season before free agency is make-or-break for any player. It's their last chance to prove they're worth a massive payday, and the pressure is on. While teams look at a player's entire career, that final year can be a game-changer. With 2026 underway, let's dive into the ten most intriguing contract years to watch, players who could be poised for superstardom... or a disappointing stumble. (Players are listed in order of their 2025 FanGraphs WAR.)
Can Skubal Join the Cy Young Elite?
All eyes are on lefty Tarik Skubal. Will he be traded before the season starts? Regardless, he's chasing history. A third consecutive Cy Young Award would put him in the same league as legends Greg Maddux and Randy Johnson. And if he keeps dominating, he could shatter Yoshinobu Yamamoto's record-breaking $325 million pitcher contract. But here's where it gets controversial: can a pitcher truly sustain this level of excellence for three straight years?
Luzardo's Health: The Million-Dollar Question
Jesus Luzardo's 2025 ERA was a misleading 3.92. A rough patch skewed the numbers, but his 2.90 FIP tells a different story – one of a dominant pitcher. With 216 strikeouts in a career-high innings count, Luzardo has the stuff. But his injury history is a red flag. Can he stay healthy for a full season and become a top free-agent target?
Chisholm: 30-30 and Ready to Cash In
Jazz Chisholm Jr. is a speedster with power. His 30-30 season in 2025, the first for a Yankee in over two decades, was impressive. Add in his solid defense and youth (just 28 next offseason), and he's a prime candidate for a big contract. But in a weak free-agent class for position players, will teams overpay for his potential?
Pivetta's Redemption Arc: Can He Keep It Up?
Nick Pivetta's $55 million deal with the Padres raised eyebrows. A 31-year-old with a history of high ERAs? But Pivetta silenced the doubters with a stellar 2025, posting a 2.87 ERA and 190 strikeouts. With an opt-out clause in 2026, he could be in line for an even bigger payday. And this is the part most people miss: Pivetta's success could signal a shift in how teams value veteran pitchers.
Peralta vs. Cease: The Durability Debate
Dylan Cease's massive Blue Jays contract highlights the value of durability and strikeouts. Freddy Peralta, seeking his fourth straight 30-start, 200-strikeout season, fits that mold. He's also been more consistent than Cease in preventing runs. But can Peralta maintain this level of performance, or will injuries catch up to him?
Sale's Last Dance: Can He Still Command Top Dollar?
Chris Sale, a veteran ace, has never tested free agency. At 37, he's entering uncharted territory. Max Scherzer's $130 million deal with the Mets at the same age offers a glimpse of what's possible. But Sale's injury history is a concern. Can he stay healthy and prove he's still an elite starter?
Rogers' Rollercoaster: Which Version Will Show Up?
Trevor Rogers has been a puzzle. His 2021 and 2025 seasons were stellar, but 2022-24 were disappointing. Which Rogers will we see in 2026? His contract year will be a defining moment, revealing whether he's a true ace or a flash in the pan.
Grisham's Redemption: Proving 2025 Wasn't a Fluke
Trent Grisham went from afterthought in the Juan Soto trade to a Yankees standout in 2025. His 34 home runs and 125 OPS+ were a dramatic turnaround. But his past performance and draft compensation penalties could limit his free-agent market. Can he replicate his success and secure a lucrative deal?
Arozarena's Power: Overcoming Strikeouts and Safeco
Randy Arozarena, like Chisholm, benefits from a weak free-agent class. Five straight 20-20 seasons with a 120 OPS+ speak for themselves. But his high strikeout rate and Seattle's pitcher-friendly park could be hurdles. Can he overcome these factors and become a top free-agent target?
King's Comeback: Opt-Out or Stay Put?
Michael King's 2025 was derailed by injuries, but his 2024 success (2.95 ERA, 201 K’s) shows his potential. His $75 million Padres deal is solid, but if he stays healthy and dominates in 2026, he'll likely opt out and aim for an even bigger contract.
Who do you think will have the biggest contract year in 2026? Will Skubal join the Cy Young elite, or will injuries derail Sale's final push? Let us know your thoughts in the comments!
