The Toughest Contract Decision Facing the Dodgers This Winter

As hard as it is to fathom the Los Angeles Dodgers' season ending with a four-game sweep at the hands of the Milwaukee Brewers, try to imagine where they would have been without Tarik Skubal.

Skubal was seen as a luxury when the Dodgers acquired him ahead of the August trade deadline. Yet when they needed a Game 1 starter for the National League Division Series against the Atlanta Braves, and the NL Championship Series against Milwaukee, the Dodgers turned to Skubal over any of the incumbents — Yoshinobu Yamamoto, Blake Snell or Tyler Glasnow.

Skubal allowed only three runs across his two postseason starts, after posting a 2.61 ERA in the regular season following the trade. The two-time American League Cy Young Award winner now enters free agency as the most coveted player on the market.

While many teams might be content to have rented Skubal for a few months at the end of his free agent walk season, the Dodgers are likely among few teams who possess the financial resources to bring him back.

Yamamoto set the market for starting pitchers with his 12-year, $325 million contract in December 2023. He was 25 at the time of his debut; Skubal will begin next season at age 30. Lop the first five years off Yamamoto's contract, and he'll be paid almost $200 million over seven years starting at age 30. Expect the numbers for Skubal to fall no short of those.

A Dodgers rotation that retains all of its "Big Four" would be formidable on paper. What makes the decision to re-sign Skubal a difficult one is where it leaves the Dodgers' rotation as they age.

Glasnow, 33, is signed through 2028. Snell, who turns 34 in December, is signed through 2029. Yamamoto, 28, is signed through 2033. Roki Sasaki, who turns 25 in November, gives the group a dash of youth. However many innings remain in the 32-year-old right arm of Shohei Ohtani do not.

The Dodgers are already well-equipped to weather injuries to anyone in that group. Right-hander Emmet Sheehan and left-hander Justin Wrobleski combined to make 44 starts in 2026; Wrobleski even made the National League All-Star team before fading down the stretch.

The Dodgers have demonstrated repeatedly that MLB's existing luxury-tax thresholds are mere speed bumps on the road to their championship ambitions. They also have a knack for finding room in their six-man rotation for as many starting pitchers as necessary, while keeping each as healthy and happy as possible.

Thus, a crowded rotation and bloated budget are not major issues when the Dodgers' front office considers re-signing Skubal.

However, if Major League Baseball prevails in its labor negotiations over the MLB Players' Association and institutes a hard cap on player salaries, the Dodgers would be more heavily impacted than any other team. That's why, monetarily, it's difficult to gauge whether Skubal is worth an investment of seven or more years.

For now, the debate centers on the duration of the commitment. Should the Dodgers extend themselves to sign arguably the best pitcher in baseball, or let another team wear the risk of injuries and decline that is demonstrably probable for pitchers older than 30 — especially with Ohtani, Snell and Glasnow presenting their own red flags?

In a rotation otherwise populated with 20-somethings, signing Skubal to a long-term contract is an easier sell (all other things being equal). For the Dodgers, there are compelling reasons on both sides of this debate, making Skubal potentially the toughest decision the Dodgers' front office will face this offseason.