After two decades of bad luck and organizational missteps, Chicago catches a break in the draft lottery. The No. 1 overall pick can change everything.
Chicago White Sox fans have had little to celebrate over the last 20 years. Ever since the 2005 team paraded through the streets of the Windy City, the organization has failed its fanbase in just about every way imaginable.
In those two decades, the White Sox have made the postseason only three times. They never advanced. They finished in 4th or 5th place in the AL Central — one of baseball’s weakest divisions — ten different times.
And somehow, despite all that losing, they never picked higher than third in the MLB Draft.
Ownership hasn’t spent. The front office has made nightmare trades that sent future stars elsewhere. And the key piece of the only successful core they managed to build became too injury-prone to ever reach their ceiling.
It has often felt like the White Sox are cursed — unlucky at best, incompetent at worst.
But that changed on Tuesday night.
From the Winter Meetings in Orlando, Major League Baseball conducted the 2026 Draft Lottery drawing, and for once, the ping-pong balls finally bounced Chicago’s way.
The White Sox landed the No. 1 overall pick.
Yes, they entered with the best odds, but it was still only a 27.73% chance. The more likely outcome was that they would slip — and in a year with a clear top prospect, the stakes were massive.
Much can change between now and July, but UCLA shortstop Roch Cholowsky is already viewed as the best college shortstop prospect in more than 20 years. Evaluators believe he’s head-and-shoulders above each of the last 10 players who went first overall. You’re talking about a franchise-altering talent — a potential superstar who could become one of baseball’s marquee young faces within a few years.
And now the Chicago White Sox are in position to draft him.
The rebuild has already taken meaningful steps forward, with a 19-win improvement from 2024 to 2025 and several rookies breaking through. But what the Sox still lack is the guy — a true cornerstone, a perennial MVP candidate, a face of the franchise who can anchor the next era on the South Side.
I’m not exaggerating when I say this might be the most important moment for the Chicago White Sox since that 2005 World Series run.
For the first time in a long time, it’s a day to rejoice, Sox fans. This could be exactly what the South Side has been waiting for.