As much as the Tigers should try to extend Tarik Skubal while they have the chance, the consensus around baseball is that they won't be able to meet his asking price. Skubal will reach free agency – if industry insiders are to be believed – as most Scott Boras clients do.
What those insiders fail to point out is the risk that comes with extending any starting pitcher, let alone Skubal. When Skubal does eventually sign on the dotted line, he will become the richest starter in baseball history. Starting pitchers are as fragile as they come, and Skubal is no exception.
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Why the Detroit Tigers can – but won't – extend Tarik Skubal
Scott Harris's mindset on extending Skubal is no secret. The Tigers acknowledge just how valuable Skubal can be at his best – he carried Detroit's rotation for much of the second half and won yet another AL Cy Young award – but they also know that formula for success has its limits.
Detroit Tigers pitchers Tarik Skubal and Denny McLain both won back to back Cy Young awards.
— Jim Miloch (@podoffame) November 14, 2025
McLain in 1968/1969 and Skubal the last two years.
Starting pitching sure has changed. pic.twitter.com/ZXIh8iyJCl
If Detroit is going to win a World Series in the next half-decade, it will not be because Skubal willed them there. It will be (perhaps with Skubal on the roster) because they assembled a deep rotation, bullpen and lineup which is up for the challenge. That sounds simple, but there's no denying how top-heavy the Tigers were this season, even at their best.
Chris Ilitch can afford to hand Skubal a blank check, one that would likely come out to around $400 million long term. In doing so, he would forfeit much of the future capital he plans to spend on the roster. For better or worse, that is how the Little Caesars CEO operates. It's far different from his father, Mike, who wanted nothing more but to watch the Tigers win a World Series prior to his death in 2017.
If these Tigers are going to achieve what Mike Ilitch's team couldn't near the tail end of his life, they will win thanks to player development and a modest payroll. That includes taking educated risks, and signing Skubal to the largest contract for a pitcher in MLB history doesn't qualify in the minds of Harris and Chris Ilitch.
Tarik Skubal, like any starting pitcher, comes with his own injury concerns
Skubal underwent Tommy John surgery in college, when he pitched for Seattle University. At the time, Skubal's baseball future was in question. The Tigers took him anyway in the ninth round, and he has rewarded that trust. However, there's a big difference between taking a draft flyer on a pitcher recently removed from Tommy John, and signing him to a record-breaking contract.
The reason I bring up an ancient surgery (from Skubal's perspective, at least) from 2016 is that, unfortunately, many starting pitchers who have Tommy John once, end up needing it a second time. Any starting pitcher who has undergone two Tommy John surgeries struggles to recover, both physically and mentally. There are always exceptions to any rule, but it's tough to know which side of that argument Skubal would fall under.
Per the National Library of Medicine, upwards to 35 percent of patients who go under the knife once to receive Tommy John, end up needing a second surgery. That is all patients – not just those who throw a baseball over 100 MPH on a regular basis.
Someone will pay Skubal his worth. They should, frankly, given his resume and age, but let's not pretend it doesn't come with some risk. As a Tigers fan, I'd love nothing more than to spend Ilitch's pizza money on the best starting pitcher in the sport. I'd welcome it, honestly. But we should not be surprised the Tigers are taking a patient approach with Skubal, and listening to trade rumors while they're at it.