The Detroit Tigers boast one of the best pitchers in baseball in Tarik Skubal, the reigning American League Cy Young award winner who pitched to the tune of 2.39 ERA last season.

Here’s the problem, though: Skubal is slated to hit free agency after 2026, and over the winter, one MLB executive predicted that the 28-year-old would land a $400 million deal.

Well, after the six-year, $170 million contract extension the Boston Red Sox just handed Garrett Crochet, Skubal may ultimately get that $400 million pay day.

Why? Well, because Crochet only has one full season as a starter under his belt, and in his one “full” year, he totaled 146 innings. By contrast, Skubal registered 192 frames in 2024 and has already made 104 starts since entering the big leagues in 2020. Crochet? Just 33.

We already know that Crochet’s new pact with the Red Sox probably made it nearly impossible for the Houston Astros to retain Framber Valdez, who will hit the open market next winter. While Skubal may operate differently from those two, he is the superior pitcher, and don’t think for a second that Scott Boras won’t use Crochet’s contract as a “look at this” at the negotiating table.

And that’s the biggest problem for the Tigers: Skubal is represented by the best, most aggressive, most stubborn agent in the business. It was Boras who secured a $765 million contract for Juan Soto earlier this offseason, and that deal could reach as much as $800 million with certain qualifiers.

You don’t think Boras will be attempting to make Skubal the richest pitcher in MLB history just like he did with Soto as a position player?

Detroit isn’t afraid to spend, but the Tigers are not the Los Angeles Dodgers or the New York Mets. They have limits, and when it comes to competing with the Dodgers, Mets and possibly even the suddenly tempered New York Yankees in free agency, it may prove difficult to retain Skubal.

Boras clients almost always hit free agency, so the chances of Detroit actually being able to sign Skubal to an extension before his contract expires are slim.

We’ll see if the Tigers can buck the trend, but Crochet’s fresh deal with Boston just made things exceedingly more difficult for Detroit.

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