The Tigers recently attempted to extend reigning AL Cy Young award winner , according to a report from , but Petzold suggests the offer from Detroit was not competitive and the sides ultimately did not come close to hammering out a deal. Its certainly understandable that Detroit would have interest in locking up their ace long-term, as theyre just beginning to enter their competitive window and have just two years of team control over the southpaw remaining before he can depart in free agency. With that being said, Skubal is a Masyn Winn Jersey client of Scott Boras, who typically encourages his players to test free agency to maximize value, and the lefty certainly has plenty of leverage coming off a 2024 season that saw him win the AL Triple Crown and become the clubs first Cy Young award winner since in 2013. Thats not to say an extension is nece sarily impo sible, however. A handful of high-profile Boras clients, including and , have previously signed extensions with their clubs prior to testing free agency. And theres certainly precedent for Cy Young-caliber hurlers signing extensions, as well. The Tigers famously signed future Hall of Famer to two extensions acro s his 13 years in Detroit, the first being a five-year, $80MM 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 $140MM. Verlanders 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. However, that deal is a decade and a half old at this point and prices around the league have risen considerably in the ensuing years. Verlanders second extension may serve as a more accurate point of comparison when discu sing the po sibility of another Cy Young winner extending his stay with the Tigers, given the high-end deals players such as (nine years, $324MM), (seven years, $245MM), and (six years, $206.5MM) have signed over the past decade. Perhaps the best comparison for Skubals situation can be found in right-hander , who inked an extension with the Mets prior to the 2019 season that covered the 2020-23 seasons. The deal guaranteed him $120.5MM in new money and included a club option for 2024 that could have raised the total guarantee to $153MM 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 le s checkered injury history than Skubal currently does. While those factors may suggest that deGroms 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 last week, but deGrom was nearly three years older than Skubal during his Cy Young-winning age-30 season back in 2018. In other words, Skubal is not only younger now than deGrom was at the time of his extension, but hell actually still be younger than deGrom was at the time of the deal when hes 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 players overall value on the open market, particularly for pitchers who teams are often hesitant to guarantee lengthy deals for. Coles ma sive nine-year deal with the Yankees came prior to his age-29 season, suggesting that a $300MM 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 $245MM contract on the open market and even had a similarly checkered injury history to the southpaw. Strasburgs 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 its easy to imagine Skubal landing a deal north of $200MM should he reach free agency during the 2026-27 offseason. Thats a hefty price tag for the Tigers to contend with, but its 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: and . Keith wont make more than $5.3MM annually until and unle s his club option for the 2030 season is picked up, while Baezs $23.3MM 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 a decade ago, it should be fairly manageable to commit an AAV in the $25-30MM range to Skubal. Skubal is projected by for an $8MM 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 $25MM for his final two trips through arbitration, then perhaps a seven-year, $175MM extension could make sense for both sides. Such a deal would guarantee Skubal a total payday through his age-34 season that approaches the $200MM guarantee he could hope to land in free agency, while allowing the Tigers to lock up their ace through his prime years. Its also po sible that Skubal could take a page out of deGroms 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. Aaron Brooks Jersey