What would it take to extend Tarik Skubal?

The Tigers recently attempted to extend reigning AL Cy Young award winner Tarik Skubal, according to a report from Evan Petzold of the Detroit Free Press, but Petzold suggests the offer from Detroit was not competitive and the sides ultimately did not come close to hammering out a deal. 

It’s certainly understandable that Detroit would have interest in locking up their ace long-term, as they’re beginning to enter their competitive window and have just two years of team control remaining before Skubal can depart in free agency. With that being said, Skubal is a client of Scott Boras, who typically encourages his players to test free agency to maximize value, and the lefty has plenty of leverage coming off a 2024 season that saw him win the AL Triple Crown and become the club’s first Cy Young award winner since Max Scherzer in 2013.

That’s not to say an extension is impossible, however. A handful of high-profile Boras clients, including Jose Altuve and Xander Bogaerts, have previously signed extensions with their clubs prior to testing free agency. And there’s certainly precedent for Cy Young-caliber hurlers signing extensions, as well. The Tigers famously signed future Hall of Famer Justin Verlander to two extensions across his 13 years in Detroit, the first being a five-year, $80M contract that bought out his final two arbitration years and three free agent years prior to the 2010 season, and the second being a five-year deal signed prior to the 2013 season that covered the 2015-19 seasons and guaranteed Verlander an additional $140M.

While Verlander’s first contract stands as a fairly straightforward comparison point to Skubal given that the lefty is also two years away from free agency and Verlander had just finished third in AL Cy Young award voting prior to the deal being signed, that deal is a decade and a half old at this point and prices around the league have risen considerably since then. Verlander’s second extension may serve as a more accurate point of comparison when discussing the possibility of another Cy Young winner extending his stay with the Tigers given the high-end deals players such as Gerrit Cole (nine years, $324M), Stephen Strasburg (seven years, $245M), and Zack Greinke (six years, $206.5M) have signed over the past decade.

Perhaps the best comparison for Skubal’s situation can be found in right-hander Jacob deGrom. deGrom signed an extension with the Mets prior to the 2019 season that covered the 2020-23 seasons. The deal guaranteed him $120.5M in new money and included a club option for 2024 that could have raised the total guarantee to $153M over five years. More importantly, the deal afforded deGrom the opportunity to opt out following the 2022 season. That deal was inked in a very similar situation to the one Skubal and the Tigers find themselves in now. deGrom was just two years from free agency and had secured his first career Cy Young award on the heels of an otherworldly season that saw him post a 1.70 ERA and 1.98 FIP in 217 innings of work.

That season was even more dominant than the one Skubal posted in 2024, and deGrom at the time had a much less checkered injury history than Skubal currently does. While those factors may suggest that deGrom’s deal ought to be a target for the lefty to shoot for, he has one major factor on his side that could substantially boost his earning power beyond even that of deGrom: age. Skubal just turned 28 on Nov. 20 while deGrom was nearly three years older during his Cy Young-winning age-30 season back 2018. In other words, Skubal is not only younger now than deGrom was at the time of his extension, but he’ll actually still be younger than deGrom was at the time of the deal when he’s slated to reach free agency following the 2026 season.

Being able to market an age-30 season in free agency is a huge boost to a player’s overall value on the open market, particularly for pitchers. Cole’s massive nine-year deal with the Yankees came prior to his age-29 season, suggesting that a $300M payday could be a stretch for Skubal, but Strasburg was a year older than Skubal will be upon reaching free agency when he secured his $245M contract on the open market and had a similarly checkered injury history to the southpaw. Strasburg’s deal wound up being among the worst contracts in recent memory due to subsequent injury woes, which could make clubs skeptical of replicating it, but it’s easy to imagine Skubal landing a deal north of $200M should he reach free agency during the 2026-27 offseason.

That’s a hefty price tag for the Tigers to contend with, but it’s certainly feasible they could put a compelling offer on the table. After all, the club has just two players signed to guaranteed contracts for the 2026 season: Javier Baez and Colt Keith. Keith won’t make more than $5.3M annually until and unless his club option for the 2030 season is picked up, while Baez’s $23.3M AAV will drop off the books following the 2027 season. For a club that was able to afford hefty annual salaries to both Verlander and Miguel Cabrera a decade ago, it should be fairly manageable to commit an AAV in the $25-30M range to Skubal.

Skubal is projected by MLBTR contributor Matt Swartz for an $8M salary via arbitration this year, and would presumably be in line for a healthy raise next winter as well. If the Tigers were willing to guarantee Skubal a combined $25M for his final two trips through arbitration, then perhaps a seven-year, $175M extension could make sense for both sides. Such a deal would guarantee Skubal a total payday through his age-34 season that approaches the $200M guarantee he could hope to land in free agency, while allowing the Tigers to lock up their ace through his prime years. It’s also possible that Skubal could take a page out of deGrom’s playbook and sacrifice some total guarantee in order to get a second bite at the apple in the form of an opt-out, perhaps following his age-32 season in 2029.