10 years, $500 million?! Who are the top suitors? MLB insiders predict Tarik Skubal's free agency

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  Kiley McDanielOct 2, 2026, 07:00 AM ET

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  • ESPN MLB Insider
  • Kiley McDaniel covers MLB prospects, the MLB Draft and more, including trades and free agency.
  • Has worked for three MLB teams.
  Co-author of Author of 'Future Value'

There has been a steady flow of elite free agents -- complete with discussion about where they might land and how big their contracts might be -- during the past few offseasons: Aaron Judge after the 2022 season, Shohei Ohtani after the 2023 season, Juan Soto after the 2024 season (and a postseason update) and then Kyle Schwarber and Kyle Tucker after the 2025 season.

This year's free agent class isn't as good top to bottom as they often are, but there is a clear prize: Los Angeles Dodgers lefty Tarik Skubal, the back-to-back AL Cy Young winner.

There are a lot of intriguing questions around Skubal's potential free agency: Will he deliver in the playoffs for the back-to-back champion Dodgers? How will teams perceive the history of procedures on his arm? Will Skubal's agent Scott Boras pull a rabbit out of his hat? Will Skubal sign before or after the expected lockout coming Dec. 1?

Given all that, it wasn't hard to get industry insiders to discuss his potential contract and the unique conditions he faces.

How much will Skubal get?

Here are the 27 contract projections from the folks I spoke with, broken into tiers of guaranteed money:

Up to $300 million (7)
4 years, $176 million
6 years, $210 million
6 years, $264 million
7 years, $280 million
7 years, $300 million
5 years, $300 million
6 years, $300 million

$300 to 350 million (7)
10 years, $325 million
8 years, $325 million
7 years, $325.5 million
7 years, $330 million
8 years, $340 million
7 years, $350 million
10 years, $350 million

$351 to 400 million (9)
8 years, $352 million
10 years, $360 million
9 years, $387 million
8 years, $400 million
8 years, $400 million
8 years, $400 million
8 years, $400 million
10 years, $400 million
10 years, $400 million

Over $400 million (4)
9 years, $450 million
10 years, $460 million
9 years, $500 million
10 years, $500 million

The average projected contract was eight years and $355 million, which is a $44.6 million average annual value (AAV). Sixteen of 27 projections (59%) were for $325 to 400 million guaranteed over seven to 10 years -- a clear sweet spot, and you'll see below why that is.

I also asked panelists whether the deal would be done before the Dec. 1 expiration of the CBA, when the expected lockout would start: 21 of 27 (78%) predicted the deal will be done before Dec. 1, similar timing to the nine-figure deals of Corey Seager, Marcus Semien, Max Scherzer, Robbie Ray, Kevin Gausman and Javier Baez that came before the 2021-2022 lockout began. Boras negotiated the first three of those contracts.

The key factors

Panelists often mentioned three standards projecting what the Skubal camp will be shooting for: Yoshinobu Yamamoto's 12-year, $325 million contract (highest pitcher guarantee), Scherzer's three-year, $130 million deal (highest pitcher AAV at $43.3 million) and Gerrit Cole's nine-year, $324 million deal (the guarantee mark Yamamoto barely beat; many think Skubal will get an inflation-adjusted version of this). Boras was the agent for the Scherzer and Cole deals.

There are two reasons panelists believe there will be a small group of teams bidding near the eventual contract: the history of how nine-figure pitcher deals have worked out and Skubal's injury history. The poor track record of pitcher megadeals is self-explanatory. A vintage one is Corbin Burnes landing $210 million guaranteed and making 14 starts over the first two years of the deal due to various arm issues. In Skubal's case, he had Tommy John surgery in 2016 while in college, a 2022 surgery on the flexor tendon in his throwing elbow and a 2026 procedure to remove a loose elbow particle.

The average age of the 32 prior pitchers to land nine-figure free agent deals was 30, which Skubal will be in a few months. His three-year platform performance entering free agency is among the best of that cohort. His ERA+ trails only Jacob deGrom (who threw less than half as many innings as Skubal in his three-year window) and narrowly falls behind Kevin Brown in 1999, the first to land such a deal.

The contenders

I didn't ask panelists who they believed would sign Skubal, but some volunteered guesses or readings of the market.

Sleepers: The Los Angeles Angels, Chicago White Sox and San Diego Padres were mentioned in this category; the Angels and Padres have new ownership, and the White Sox have a new owner in waiting.

In most high-end free agent bidding processes, there's at least one surprising or mystery team. After circling back with some sources after the projections were in, the Padres seemed to be the consensus pick for the most serious bidder in this group.

True contenders: The Dodgers, Detroit Tigers and New York Mets came up most often for this category, though the Tigers were mentioned as more likely to be on the periphery than a true contender. Most insiders project the Dodgers and Mets to be serious bidders, but there is some hesitation surrounding the Dodgers given the controversy around the team's ownership. Some thought the Mets might be looking to do a shorter-term deal such as they did with Bo Bichette, which might not work if Skubal is looking to set a record for guaranteed money.

The New York Yankees were just behind that lead group in total mentions. For those who thought the Dodgers wouldn't break the bank, and the Mets would only offer AAV-record deals, the Yankees were a common fallback. Brian Cashman has landed Cole, Max Fried and Carlos Rodon in free agency in the last half dozen years and adding Skubal to a group that also includes Cam Schlittler, Ryan Weathers, Will Warren and Clarke Schmidt would give the Yankees the best starting pitching in the sport. That much depth likely would necessitate a trade.

Skubal's strategy

There were some projections of opt-outs, with four panelists laying out a contract with multiple opt-outs. Deferrals also came up from four panelists. Although there is some suspicion they might be outlawed in the new CBA, there also was general agreement that Boras and Skubal will be going for the biggest total guarantee, which can be juiced on paper with deferrals.

Opt-outs and deferrals are two common levers for agents to pull in free agent contract negotiations, but Skubal's specific situation might include another notable lever: a big signing bonus. One panelist thought Skubal would get almost 20% of the guarantee from his projected contract in the form of a signing bonus, half of that payable before the Dec. 1 expiration of the current CBA.

The thinking behind that would be to 1) be sure to be paid this year, even if a season doesn't happen and 2) if a season is shortened and salaries are paid pro rata, the bonus wouldn't be reduced the way a salary would be. There are also possible personal tax advantages to Skubal if he's paid before playing for a new team, which could have higher state income taxes than where he lives in the offseason. An agent summed up the strategy: "As much up front as possible ... not sure if owners will allow it."

Skubal's injury history also was a point of discussion, with the belief he could go for a shorter-term deal and shoot for the AAV record. If his long-term options aren't to his liking, could a team come in with four years, $200 million with opt-outs and injury language (a year added to the deal at a lower salary if he has an elbow surgery, for example)?

Panelists largely thought Skubal would go for the biggest total guarantee, but when I floated the AAV-buster scenario, a strategy that the Mets employed to land Bichette last winter, many reconsidered. Maybe a few teams take that approach, and Skubal's process plays out like Tucker's free agency last offseason, when he signed a four-year, $240 million deal with the Dodgers.

The final thing to consider is simply how many teams will be bidders above the $325 million mark, which is widely believed to be the first standard Skubal wants to clear. It's always hard to predict these things as it's an ownership-level call, but the list of clubs that would pay the expected market price for a long-term deal on a 30-year-old pitcher with three procedures on an elbow can't be long. Some teams will be philosophically out due to years, position and age, but Skubal and Boras need only two teams to make a bidding war possible. Based on the previous free agent contract polls I've done, clearly the best player on the market tends to overperform the projections.