The Tigers recently tried to extend the AL Cy Young award Tarik Skubalaccording to a report from Evan Petzold of the Detroit Free Pressbut Petzold suggests that Detroit’s offer was not competitive and that the parties ultimately did not come close to reaching an agreement. It’s certainly understandable that Detroit would have interest in locking down their ace for the long term, as they are just starting to enter their competitive window and only have two years of team control over the lefty before he can leave in free agency. That being said, Skubal is a client of Scott Boras, who typically encourages his players to test free agency to maximize value, and the southpaw certainly has plenty of leverage after a 2024 season that saw him win the NFL’s Triple Crown. ‘AL and become the club’s first Cy Young Award winner since Max Scherzer in 2013.

However, this does not mean that an extension is necessarily impossible. A handful of prestigious Boras clients, including Jose Altuve And Alexandre Bogaertshave already signed extensions with their clubs before testing free agency. And there’s certainly precedent for Cy Young-caliber pitchers signing extensions, too. The Tigers signed the future Hall of Fame Justin Verlander to two extensions during his 13 years in Detroit, the first being a five-year, $80 million contract that bought out his final two arbitration years and three free agent years before the 2010 season, and the second being a five-year contract signed before the 2013 season that covered the 2015-19 seasons and guaranteed Verlander an additional $140 million.

While Verlander’s first contract makes for a fairly easy point of comparison with Skubal given that the southpaw is also two years away from free agency and Verlander had just finished third in AL Cy Young Award voting before the signing of the deal, this deal has lasted a decade and a half at this point and prices around the league have increased significantly in the years since. Given this, 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 high-end player deals such as Gerrit Cole (nine years, $324 million), Stephen Strasburg (seven years, $245 million), and Zack Greinke (six years, $206.5 million) signed over the past decade.

Perhaps the best comparison to Skubal’s situation is at right-handed Jacob of Grom. deGrom signed an extension with the Mets before the 2019 season that covered the 2020-23 seasons. The deal guaranteed him $120.5 million in new money and included a club option for 2024 that could have brought the total guarantee to $153 million over five years. More importantly, the deal gave deGrom the option to opt out after the 2022 season. This deal was signed in a very similar situation to the one Skubal and the Tigers find themselves in currently; deGrom was just two years away from free agency and had earned his first career Cy Young Award on the heels of an otherworldly season that saw him post a 1.70 ERA and 1,000 FIP, 98 in 217 innings of work.

This season was even more dominant than the one Skubal posted in 2024, and deGrom had a much less checkered injury history then than Skubal does now. While these factors might suggest that deGrom’s deal should be a target for the southpaw, he has one major factor on his side that could significantly increase his earning power beyond even deGrom’s: age. Skubal just turned 28 last week, but deGrom was nearly three years older than Skubal during his Cy Young-winning age-30 season in 2018. In other words, Skubal isn’t just younger now than deGrom was at the time of his extension, but he will actually be even younger than deGrom was at the time of the deal, when he is expected to hit free agency after the season 2026.

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, especially for pitchers for whom teams are often reluctant to guarantee long-term contracts. Cole’s massive nine-year contract with the Yankees came before his age-29 season, suggesting a $300 million salary might be a bit of a stretch for Skubal, but Strasburg was a year older than Skubal won’t have it when he hits free agency when he gets his $245. MM contract on the open market and even had a similarly checkered injury history for the southpaw. Strasbourg’s deal turned out to be one of the worst contracts in recent memory due to subsequent injuries, which could make clubs skeptical of his repeat, but it’s easy to imagine Skubal doing a deal at north of $200 million if he reaches free agency during the 2026-27 season. offseason.

That’s a steep price for the Tigers, but it’s certainly possible they could bring an attractive offer to the table. After all, the club only has two players signed with guaranteed contracts for the 2026 season: Javier Baez And ColtKeith. Keith will make no more than $5.3 million per year until his club option for the 2030 season is selected, while Baez’s $23.3 million AAV will disappear from the books after the season 2027. For a club that was able to pay high annual salaries to both Verlander and Miguel Cabrera Ten years ago, it should be pretty manageable to commit an AAV in the $25-30 million range to Skubal.

Skubal is screened by Matt Swartz, MLBTR contributor for an $8 million salary via arbitration this year, and would likely be in line for a nice raise next winter as well. If the Tigers were willing to guarantee Skubal a total of $25 million for his final two trips to arbitration, then perhaps a seven-year, $175 million extension could make sense for both sides. Such a deal would guarantee Skubal a total salary through his age-34 season that comes close to the $200 million guarantee he could expect to land in free agency, while allowing the Tigers to retain their ace during his early years. It’s also possible that Skubal could take a page from 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 after his age-32 season in 2029.