The Pirates struck gold with Paul Skenes — a reminder of how one lucky lottery night could do the same for the White Sox.
Major League Baseball has crowned its World Series champion, and the Los Angeles Dodgers have done it again — going back-to-back to defend their title.
Now, all eyes turn to the offseason. Twenty-nine other clubs are chasing the Dodgers, each trying to close the gap on baseball’s model franchise. Easier said than done. Between the depth of their roster and the size of their wallet, the Dodgers aren’t slowing down anytime soon.
They’re expected to be aggressive in free agency yet again. But as always, there are levels to it. Some teams will tweak playoff-caliber rosters. Others will try to build true contenders. And then there are clubs like the Chicago White Sox — just trying to take the next step toward relevance.
A Crucial Winter for the South Side
White Sox fans have reason to hope this offseason, though history has trained them to brace for disappointment. Whether or not Chris Getz and the front office can deliver meaningful progress remains to be seen.
But regardless of what happens in free agency or the trade market, there’s one date this winter that looms larger than all the rest for the White Sox:
December 9.
That’s when the MLB Draft Lottery will take place during the Winter Meetings in Orlando. The White Sox hold the best odds at landing the No. 1 overall pick in the 2026 MLB Draft — and the outcome of that drawing could shape the next decade of baseball on the South Side.
It’s not hyperbole to say December 9 could become a defining moment in franchise history.
The Paul Skenes Example
Just look at the Pittsburgh Pirates. They went 62-100 in 2022. The A’s and Nationals finished with worse records, and the Reds were tied with them — yet some lottery luck gave Pittsburgh the top pick in the 2023 draft.
They used it on Paul Skenes.
Two years later, Skenes is already a two-time All-Star and the likely 2025 NL Cy Young Award winner. He’s the kind of arm that transforms a franchise — either by leading it to October or by becoming a massive trade asset. The Pirates hit the jackpot that day, and it changed everything.
Even if Pittsburgh hasn’t fully reaped the rewards of that pick just yet, Paul Skenes gives them an ace in the hole — a get-out-of-jail-free card. He’s either the foundation of their future or the centerpiece who could kick-start their next rebuild. Skenes is arguably the most valuable asset the Pirates have had in decades — even more valuable than Chris Sale was in his prime.
All because the lottery balls bounced their way.
Building a Core, But Missing a Face
The White Sox have already laid down a promising foundation. Colson Montgomery, Kyle Teel, and Shane Smith were among the best rookies in baseball in 2025. More talent — like Braden Montgomery and Hagen Smith — isn’t far behind.
What the previous rebuild lacked, though, was a true face of the franchise. José Abreu filled that void admirably, but he was already on the back end of his career by the time the Sox finally broke through. And that breakthrough was short lived.
Like we just saw with Vladimir Guerrero Jr. and the Blue Jays during their recent run, the White Sox need a young superstar they can build around — the kind of player who defines an era. For an organization that doesn’t spend heavily in free agency, the easiest way to land that kind of talent is through the draft.
As of today, the consensus top prospect for the 2026 MLB Draft is UCLA shortstop Roch Cholowsky — though plenty can change between now and July. A high-school phenom could emerge, or college arms could rise with big spring performances.
Whoever it ends up being, one thing is clear: the White Sox absolutely cannot afford to miss. The 2026 Draft must be a home run.
December 9, 2025, could go down as one of the most important days in modern franchise history — no matter which way the lottery balls bounce.