The Detroit Tigers are navigating through the off-season with a major dilemma—trade Tarik Skubal now or risk losing him for nothing in 2026? If you ask insiders like Jeff Passan whether the Tigers can move away from the ace, the answer would be—they need to!

Jeff Passan, in fact, even lists the Yankees as a team that could land the back-to-back Cy Young winner Tarik Skubal in a trade this offseason. But here is where things get interesting- he even says that to land Tarik Skubal, the Yankees would have to give up some arms.

And honestly, there are a few names of top prospects and young arms of the New York Yankees that come to mind. Names like Cam Schlittler, Will Warren, Clarke Schmidt, and Luis Gil are all Detroit Tigers that may be interested in trading for.

Sure, losing these players would hit the New York Yankees’ depth and development pipeline hard, but everyone knows how high the stakes are for them this time. They have not only prolonged the drought of the championship, but even after being one of the teams with the highest payroll, they embarrassingly ended their season. So they need depth, they need major changes, and Skubal can bring one.

And of course, to get an arm like Skubal’s would be expensive. He has been one of the league’s most dominant pitchers in the last two seasons. The two-time All-Star had won the pitching Triple Crown in 2024, going 18-4 with a 2.39 ERA, 0.92 WHIP, and 228 strikeouts across 192 innings. Then he somehow topped it, winning another ERA title last season with a 2.21 mark, a 13-6 record, a 0.89 WHIP, and 241 strikeouts over 195.1 innings.

With Skubal in the rotation, the Tigers could reach the postseason back-to-back and were just one win shy of the ALCS in both 2024 and 2025. No pitcher has been more central to a team’s identity and success like that. That’s why the Tigers will hesitate, but then they cannot risk letting Skubal walk for nothing. That could be even worse, and the Tarik Skubal deal could bring Detroit a franchise-shifting return with multiple top prospects from the Yankees—maybe even long-term pieces.

And it’s not just the Yankees who could go the extra mile for Skubal; even the Dodgers could. This could become one of the biggest storylines this winter!

Red Sox reunion with Alex Bregman could open the door for Tarik Skubal

Now talk of the New York Yankees and, of course, their rival Boston Red Sox enters the picture—and honestly, they could make the pinstripe chase for Skubal tough. And it all starts with Alex Bregman. So, there is a growing buzz that Boston might be heading towards a reunion with Bregman. He is the best third baseman on the free agent market, and he brings a veteran eye to the young roster. But Boston is not the only team eyeing him.

The Tigers, who missed on Alex Bregman, are eyeing him too, and they could jump back in. In fact, Tarik Skubal recently commented on Bregman, saying, “He’s a great player… I’d love to play with him… Hopefully, we can do it again this year.” Isn’t this sounding like a recruiting pitch?

And here is where things get interesting. Skubal becomes a free agent after 2026, and if adding Bregman convinces the Cy Young winner to stay, then the Tigers might push more than anyone. But this same logic applies to Boston. The Red Sox not only need a third baseman after trading their homegrown star to the Giants last year, but Bregman could also be key to convincing Tarik Skubal to come to Boston.

The real question is whether the Boston Red Sox are ready to act like a big-market powerhouse again. They had waited until February to sign Bregman the first time, and they have been away from the free agents who are high-profile. Plus, the 2027 lockout makes teams signing huge deals tricky. The Sox need Bregman, and bringing him back may have them chasing Skubal—is this too far-fetched? We think not!