As the Detroit Tigers stare down the final season of Tarik Skubal’s team-controlled years, the organization faces one of the toughest calls in baseball. The 2024 Cy Young winner is about to hit the open market after 2026, and extension talks have gone quiet.
With every passing week, the idea of trading the game’s most dominant left-hander before he walks for nothing looks less like a last resort and more like sound business.
Few teams are better positioned to meet Detroit’s sky-high asking price than the Boston Red Sox. After another postseason-less October, Boston’s rotation remains the clearest weakness on an otherwise ascending roster. Plugging Skubal alongside Garrett Crochet (acquired last winter) would instantly create the most feared one-two punch in the American League.
Bleacher Report’s Zachary D. Rymer laid out the math that underscores why the Tigers can—and probably should—play hardball this offseason. He also predicted that the Red Sox would be the team to acquire Skubal.
“Even though Skubal is likely to earn close to $20 million in his last year before free agency, Baseball Trade Values puts his surplus value at a little over $60 million,” Rymer wrote. “That’s close to twice as much surplus value as Corbin Burnes had when the Milwaukee Brewers rented him out to the Baltimore Orioles two winters ago, so the Tigers have every right to not move Skubal unless they get everything they ask for.
“To this end, multiple top-100 prospects would be a must. The Tigers could also try to replace him in their 2026 rotation, either with an MLB-ready prized pitching prospect or someone who already has No. 1 credentials in the bigs.”
Translation: Detroit isn’t settling for a decent haul—they want a franchise-altering package. Boston has the ammunition. Marcelo Mayer, Roman Anthony, and Kristian Campbell headline a farm system deep enough to surrender two or even three top-100 talents while still keeping elite depth. Add in big-league pieces like Triston Casas or Wilyer Abreu if the Tigers want immediate help, and the framework starts to take shape.
For the Red Sox, the calculus is simple: Skubal doesn’t just patch a hole—he catapults them back into legitimate contention in the AL East. Pairing the reigning Cy Young winner with Crochet would give Boston a rotation ceiling rivaled only by the Yankees and Orioles on paper. The catch, of course, is money. Any trade would almost certainly come with the expectation—or at least the strong hope—that Skubal signs a long-term extension, likely in the range of seven to ten years and north of $250 million.
That’s where the gamble lives. The Red Sox have been cautious with megadeals in recent years, but passing on a 28-year-old ace entering his prime would be a missed opportunity of historic proportions.
Detroit, meanwhile, would reset its contention clock with an influx of blue-chip talent while avoiding the nightmare scenario of watching Skubal sign elsewhere for nothing but a compensatory draft pick.
The fit is almost too perfect, which is exactly why so many around the game remain skeptical it actually happens. When a pitcher is this good, this young, and this cost-controlled, teams rarely let go—unless the return is so overwhelming that saying no becomes the harder choice.
This winter, the Tigers might finally get an offer they can’t refuse. And if they do, Fenway Park could be the new home of the best pitcher on the planet.
