Tarik Skubal, the Detroit Tigers’ best pitcher, is about to become a free agent. And their president of baseball operations, Scott Harris, has to choose between keeping Skubal, who is worth $5 million in compensation, and trading an ace for something that isn’t guaranteed to happen.

If Harris “fails on the trade front,” it could impact his tenure at the org. The stakes couldn’t be higher. Skubal will be 29 before Thanksgiving, and is on track to win the Cy Young Award twice. He is the Tigers’ best chance to make it to the World Series in 2026.

The Tigers’ first half of 2025 gave fans hope as they became the first team to reach 60 wins. However, their second-half collapse made people wonder what was going on. So, the Skubal situation is critical right now.

At the end-of-season press conference on October 13, Harris talked about his cautious philosophy. He said that every offseason, he doesn’t try to “chase the flashier name and offer a lot of money” like some other teams do. But this rule might not apply to his own time in office.

Scott Boras is Skubal’s agent, and it looks like he is set on testing free agency even though Detroit can’t finish contract talks. Other teams view Skubal as a one-year rental, making him much less valuable in trade talks. Harris could keep the ace until 2026, but if he doesn’t, and Skubal leaves, he would get the same criticism that Ilitch gave Avila.

This choice brings back memories of the organization’s past high-wire acts.

Three years ago, Ilitch publicly criticized Avila’s trades. The message spread throughout baseball: making big moves that don’t work out can hurt your career. Harris now has to decide if keeping Skubal means stability or stagnation, and if trading him means vision or panic.

The Detroit Tigers showed that they could win 60 games first in early 2025. If Harris lets that momentum fade away without using his star pitcher to win a championship, he could end up being another cautionary tale in Tigers history.

Why the Tigers can’t afford to lose Skubal

Skubal’s case makes it clear what Harris is really up against: a pitcher who is Detroit’s only real chance for a 2026 WS run. If Harris lets Skubal go without winning a championship, it will make his credibility problem worse, not just with ownership but also with the team’s rebuilding story.

Skubal’s dominance was the foundation of the Tigers’ plan for 2026.

He won the Cy Young award last year and had a 2.21 ERA in 31 starts, striking out 241 batters and proving that he was baseball’s most dependable ace. The way he pitched six innings against Seattle in the divisional round showed exactly why Detroit built its rotation around him. The Tigers may go from being contenders to pretenders in the AL Central without Skubal.

Harris understands this calculus, yet time works against him.

According to Ken Rosenthal, a Tigers staffer made their position crystal clear: “We want to win with him.” The clock is running out, though. Rosenthal notes that “top Scott Boras clients hardly ever sign extensions when they are this close to free agency,” so Detroit’s chance to lock up its best player is almost gone.