The Boston Red Sox have a golden opportunity to build one of MLB’s most fearsome pitching duos by pairing Garrett Crochet with Tarik Skubal, the Detroit Tigers’ ace and likely two-time AL Cy Young Award winner. While no official reports confirm Skubal’s availability, whispers among analysts suggest the Tigers might consider trading the 29-year-old lefty this offseason as he enters his final year of arbitration. For a Red Sox team desperate for a top-tier arm, landing Skubal could be a game-changer—but only if they don’t repeat the Yankees’ mistake with Juan Soto.
Skubal is in the midst of a historic run, dominating hitters with a sub-1000-inning career that makes him even more valuable due to his relatively low mileage. Experts predict that if he hits free agency, he’ll become the highest-paid pitcher in baseball. The Tigers could lock him up with a long-term extension and keep him as a lifelong Tiger, but insiders doubt Detroit has the financial muscle to make it happen. With no extension talks reportedly underway, the Tigers face a tough choice: trade Skubal now or risk losing him for nothing in free agency next offseason.
Enter the Red Sox, one of the few teams with both the prospect capital and financial firepower to make this deal a reality. Boston’s farm system is loaded with pieces that could entice Detroit, and the Fenway Sports Group has shown it’s not afraid to spend big. Just look at their recent moves: they were ready to pay Alex Bregman $40 million a year (before he opted out), with Rafael Devers locked in at $28 million annually and Trevor Story earning $25 million. Money isn’t the issue here—commitment is.
The cautionary tale? The New York Yankees. After trading for Juan Soto, they banked on extending him post-2025 World Series, only to watch the Mets swoop in with a bigger offer. The Mets, by contrast, got it right with Francisco Lindor. When they traded for him from Cleveland at a similar career stage as Skubal, they didn’t have a contract in place but knew they’d get one done. And they did. Boston needs to take notes.
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If the Red Sox want to trade for Skubal, it’s going to cost them major prospects—think top-tier talent to land a pitcher who’s neck-and-neck with Paul Skenes as the best in the game. But no team, including Boston, will part with that kind of capital without a guarantee that Skubal stays long-term. Chief Baseball Officer Craig Breslow knows this. He’s no stranger to blockbuster deals, but he’ll need owner John Henry to back him with a blank check to secure Skubal’s extension.
The bottom line: if Boston wants to land Skubal, they can’t just trade for him—they have to lock him up. The Yankees whiffed on Soto by hoping for the best. The Red Sox can’t afford to make the same mistake. With Crochet already in the rotation, adding Skubal could make Boston’s pitching staff the envy of MLB. But it all hinges on one thing: a massive, long-term contract to keep Skubal in a Red Sox uniform for years to come. Don’t blow it, Boston.