Will Tarik Skubal Land Historic $400M Contract? Rumors on SP Eyeing Yamamoto's Record

One year away from free agency after winning back-to-back American League Cy Young awards, Detroit Tigers ace Tarik Skubal has his sights set on landing the richest contract for a pitcher in MLB history.

Per The Athletic's Jim Bowden, Skubal's camp is "waiting" for the Tigers to make him a proposal that would far surpass their previously reported offer and potentially exceed Yoshinobu Yamamoto's deal with the Los Angeles Dodgers.

ESPN's Kiley McDaniel added there's a chance Skubal ends up becoming the first pitcher to sign a contract worth at least $400 million whenever he does sign.

The first big question is how serious the Tigers are going to be in their efforts to retain their superstar pitcher. Jon Heyman of the New York Post reported in October there was a gap of $250 million between what Skubal was seeking and what Detroit offered after his first Cy Young season in 2024.

A subsequent report from Heyman noted the Tigers' offer at that time was worth $80 million over four years.

If Yamamoto's deal is the starting point for Skubal, that does represent a gap of about $250 million. The Dodgers signed Yamamoto to a 12-year, $325 million contract in December 2023 that made him the highest-paid pitcher in MLB by total value.

There are some factors that could hold teams back from going that far on a Skubal deal. Yamamoto was 25 when he signed with the Dodgers. Skubal will be entering his age-30 season in 2026.

Gerrit Cole, who was the highest-paid pitcher before Yamamoto, got a nine-year, $324 million contract from the New York Yankees as a free agent going into his age-29 season.

The only other pitchers with contracts currently worth at least $200 million are Max Fried and Corbin Burnes. Both of them signed their deals entering their age-30 seasons.

Even though Skubal has undeniably been better than Fried or Burnes when they became free agents, how eager are teams going to be to give the type of long-term pact it would take to sign him with injury rates for pitchers on the rise in recent years?

Cole missed all of 2025 after undergoing Tommy John surgery in March. Burnes looked very good in 11 starts for the Arizona Diamondbacks after getting his big contract, but his season ended in June due to an elbow injury that required Tommy John surgery.

Skubal has been durable over the past two seasons, making 62 starts, but he missed the final two months of 2022 and first three months of 2023 due to flexor tendon surgery on his left elbow.

There's also the matter of MLB's labor relations since the current collective bargaining agreement expires on Dec. 1, 2026. Indications at this point are there will be a work stoppage with owners expected to push for a salary cap that the MLB Players Association doesn't want.

If there is some sort of cap implemented, the entire salary structure in MLB would be overhauled.

On merit, Skubal absolutely deserves a record-breaking contract. He leads MLB in fWAR (12.6), ERA (2.30), FIP (2.47), ranks second in strikeout-to-walk percentage (26.7) and third in strikeouts per nine innings (10.9) since the start of 2024. The southpaw became the first pitcher to win consecutive Cy Young awards since Jacob deGrom in 2018 and 2019.