Chicago White Sox fans know all about being hamstrung by an owner. Jerry Reinsdorf’s refusal to spend in free agency has set the organization back for more than a decade.

Chicago remains one of just two MLB franchises (Athletics) to have never handed out a contract worth more than $100 million in total value. Because of that, the White Sox constantly find themselves trading away premier talent instead of extending their own stars.

Take Chris Sale, for example. A five-time All-Star with the White Sox, he finished top five in AL Cy Young voting four years in a row and racked up four straight 200-strikeout seasons. Sale had a career ERA right at 3.00, a clean bill of health, and was just 27 years old when the White Sox traded him to Boston.

Yes, that deal jumpstarted the last rebuild — but it also symbolized everything wrong with this franchise. Even if they wouldn’t admit it publicly, the Sox traded Sale because they knew they’d never pay to keep him.

The same thing happened with Garrett Crochet. After breaking out in 2024 as a first-year starter, Crochet looked like a legitimate ace — an All-Star at 25 with electric stuff. That’s the kind of pitcher you build a rotation around. But with just two years of team control remaining and ownership unwilling to commit big money, Crochet was shipped to Boston… where he immediately signed a $170 million extension.

All he did after that? Go 18–5 with a 2.59 ERA and an MLB-best 255 strikeouts, likely finishing as the runner-up for the 2025 AL Cy Young Award.

Dylan Cease? Same story. He was the Cy Young runner-up in 2022 with Chicago, but was traded before 2024 so the Sox could “maximize value” before they had to actually pay him.

It’s the same, old, sad cycle. Even when trades like the Crochet deal end up returning useful pieces, it’s hard for fans to feel inspired knowing that any player who becomes elite will be traded away within five years — all because ownership refuses to invest.

The Tigers Are Making the Same Mistake as the White Sox

If it’s any consolation, White Sox fans, a division rival might be about to repeat your same mistakes.

After a heartbreaking extra-inning loss in Game 5 of the ALDS, reports from Jim Bowden suggest the Detroit Tigers are planning to shop superstar pitcher Tarik Skubal this offseason.

Skubal is under team control through 2026. On the open market, he’d likely command half a billion dollars — and the Tigers apparently don’t want to be the ones writing that check.

He’s led the American League in ERA two years running, going 31–10 with a 2.30 ERA and 469 strikeouts since the start of 2024. He’s about to become the 12th pitcher in MLB history to win the Cy Young in back-to-back seasons.

And now they might trade him? That would be one of the biggest self-inflicted wounds in modern baseball.

Trading Skubal Would Open Up the AL Central

This franchise went nine years without a playoff appearance. Now, after finally breaking through — 87 wins in 2025, their most since 2014 — Detroit looks like a team on the rise. The AL Central is wide open: the White Sox and Twins are rebuilding, the Royals disappointed, and Cleveland’s late surge doesn’t hide Detroit’s superior roster on paper.

If the Tigers extend Skubal and keep their core together, they can own this division for years. Instead, they’re considering tearing it down over fear of a price tag — and this from the same team that once paid Jordan Zimmermann $110 million and Javy Báez $140 million.

Tarik Skubal is worth every penny.

If Detroit wants to shoot itself in the foot, that’s their choice. White Sox fans certainly won’t complain about a division contender voluntarily getting worse — not while Chicago is finally trying to climb back up the mountain.

But Sox fans have seen this movie before. And they know exactly how it ends.