Chicago’s loyal fan base isn’t demanding megadeals — just meaningful investment. Instead, they’re staring down another offseason of one-year Band-Aids and recycled excuses.
Chicago White Sox fans don’t ask for much. One of the most tortured fan bases in all of sports somehow manages to temper expectations year after year — a skill that’s become as ingrained in the South Side experience as tailgates in Lot B or dollar dog nights at Rate Field.
Heading into free agency this winter, there’s no reason the White Sox shouldn’t be looking to supplement their young core with a few steady, veteran additions. It’s not like fans are clamoring for Kyle Tucker with a $400 million price tag. They’d just like to see an honest investment — a signal that this rebuild is meant to go somewhere.
Fans want a reason to tune in for 2026 beyond simply watching the young core develop. Because even as rookies like Kyle Teel, Shane Smith, and Colson Montgomery shined in 2025, it was hard to take the team seriously when players like Jacob Amaya, Bobby Dalbec, Nick Maton, and Michael A. Taylor were still getting regular at-bats early in the season.
Yet here we are again.
The White Sox remain one of only two franchises in baseball that have never handed out a contract worth more than $100 million. It’s ridiculous that this is still true in 2025. But even asking for something as reasonable as Josh Naylor for $60 million over four years somehow feels far-fetched on the South Side.
And of course, it is.
Even with a young core that flashed promise in 2025 — and glaring needs at first base, right field, and the back half of the bullpen — multi-year contracts still aren’t Jerry Reinsdorf’s style.
General manager Chris Getz is already bracing the fanbase for disappointment.
“To go beyond this upcoming season I think would be a little premature considering the state of our club,” he said recently.
Let that sink in, Sox fans: another offseason of one-year deals and bargain-bin promises.
Maybe Rhys Hoskins becomes a stopgap at first base. He’ll be coming off a Grade 2 UCL sprain in his left thumb that cost him playing time in Milwaukee. Maybe Kenley Jansen takes a one-year flyer similar to the $10 million deal he signed with the Angels last offseason and delivers 30 saves out of the bullpen. Those are the kinds of moves the White Sox can stomach.
And to be fair, they’d help. Those signings would make the 2026 team a little better, maybe even interesting for a while. But they don’t make the White Sox contenders — and more importantly, they don’t fix anything long-term.
It’s the same story, every winter. And short-term contracts just mean the same holes today will be holes next year.
The same cycle of patchwork solutions, followed by disappointment, followed by another rebuild. You can blame the impending lockout or the uncertainty of a new collective bargaining agreement — and I’m sure Jerry Reinsdorf will — but this isn’t new. This is who they’ve always been.
And until that changes, White Sox fans will keep doing what they do best: showing up, staying loyal, and expecting nothing — because history tells them that’s exactly what they’ll get.