The 10 Most Interesting Contract Years to Watch in 2026
The contract calendar flips to 2026 with a mix of pressure and timing that makes this year especially fun to track. Stars are either chasing historic money, weighing home-state pulls, or deciding whether to lock in security or gamble on one more big season. Here are the players whose next seasons come with more at stake than most.
Tarik Skubal
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Detroit’s ace enters 2026 coming off a 6.6 fWAR season, which ranked among the most valuable pitching years in baseball in 2025. At 29 years old, Tarik Skubal is chasing a third straight Cy Young Award, something only Greg Maddux and Randy Johnson have ever done. Another season anywhere near his recent level could put him in a position to top Yoshinobu Yamamoto’s $325 million pitching contract. Trade rumors remain part of the backdrop, since elite starters with one year left rarely stay put on the market.
Jesús Luzardo
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The surface numbers hide how strong last season actually was, with Jesús Luzardo finishing 2025 with a 3.92 ERA, but a 2.90 FIP tells a more accurate story of his performance. He struck out 216 hitters across 183 2/3 innings, both career highs, while pitching for Philadelphia after an offseason trade. Durability is the open question, since he has topped 18 starts only twice, but he hits free agency at age 28 with real upside.
Jazz Chisholm Jr.
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Jazz Chisholm Jr. posted the first 30 home run, 30 stolen base season by a Yankees player in more than 20 years during 2025. He also delivered a 125 OPS+ while handling second base defensively after a midseason position shift. An oblique strain cost him over a month, but he still reached 4.4 fWAR. The upcoming free-agent class lacks impact bats, which works in his favor.
Nick Pivetta
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By having Nick Pivetta, San Diego’s gamble is already looking smart. He responded to a four-year, $55 million deal by posting a 2.87 ERA with 190 strikeouts over 181 2/3 innings. He had never finished a season with an ERA below 4.04 before 2025, which made the jump stand out across the league. An opt-out after 2026 gives him a clear incentive to prove last year was repeatable.
Freddy Peralta
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Consistency drives value, and that’s been Freddy Peralta’s calling card, who kept his ERA at 3.86 or lower for five straight seasons. He turns 29 during the year and could be aiming for a fourth consecutive season with at least 30 starts and 200 strikeouts. Dylan Cease’s seven-year, $210 million deal shows how much teams pay for reliable innings paired with swing-and-miss stuff.
Chris Sale
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Chris Sale’s resume already includes a Cy Young Award and multiple All-Star appearances. He enters his age-37 season having never tested free agency, thanks to a long trail of extensions. His 2024 Cy Young was followed by an injury-affected but productive 2025. Max Scherzer’s three-year, $130 million contract at the same age provides a recent reference point if Sale reaches free agency.
Trevor Rogers
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Trevor Rogers posted a 1.81 ERA in 2025 after struggling through a 5.09 ERA stretch from 2022 to 2024. His 2021 season included a 2.64 ERA and frontline metrics, which still shape how teams view him. A clean walk year could settle the debate about which version is real.
Trent Grisham
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The context around Trent Grisham’s 2025 season matters. He hit 34 home runs with a 125 OPS+ while starting 124 games in center field after Juan Soto left New York. From 2022 to 2024, he posted an OPS+ of 84 across 381 games, which made the breakout stand out. He accepted a $22.025 million qualifying offer to reset his market without draft penalties.
Randy Arozarena
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Production has followed Randy Arozarena from city to city; he recorded five straight 20-home run, 20-steal seasons with a combined 120 OPS+. Seattle’s ballpark suppresses offense, yet his numbers have held steady. He enters free agency slightly older than Chisholm but with a track record that still plays well in a thin-hitter market.
Michael King
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Health will decide the ceiling. Michael King showed in 2024 that he could handle a starter’s workload with a 2.95 ERA and 201 strikeouts. Injuries limited him to 15 starts in 2025, which muted his value despite a solid performance. He signed a three-year, $75 million deal and could opt out after 2026 if the innings return.