Do all roads lead to despair for the White Sox under Jerry Reinsdorf’s ownership?

There is only one possible happy ending for the team, and it’s an unlikely one

All optimism for the Chicago White Sox’s 2025 season has been extinguished as rapidly as it was built up. The Sox started the season strong with an Opening Day win over the Angels, but Chicago is back to disappointing fans as the sole owners of last place in the AL Central riding a five-game losing streak. Similarly, on the management side of the organization, the Sox are facing a setback, as any hopes of ownership changes were recently squashed.

USA Today’s Bob Nightengale, who we all know is the “Deep Throat” of White Sox executive messaging, recently revealed that Sox owner Jerry Reisndorf has no intention of selling the team “as long as he remains in good health.” According to Nightengale, Reinsdorf has “rebuffed all of minority investor Justin Ishbia’s requests to purchase controlling interest of the team.”

For Sox fans, who have long awaited Reinsdorf’s relinquishment of the team, this is beyond infuriating. Although it was hard to believe that Reinsdorf would go through with a sale when he first announced his interest in putting the team on the market in October, hope lingered when Ishbia bought most minority owners’ shares earlier this year, improving his stake and standing over the franchise’s control. As it turns out, Reinsdorf wasn’t fully committed to seeing the Sox succeed, at least without him in the picture (shocker), so it’s no surprise that the 44-year owner of the club suddenly lost interest in selling. Chicago fans shouldn’t feel bad that they drank Reinsdorf’s Kool-Aid — at least when Jerry was the one making and drinking his own Kool-Aid, too.

With a greedy billionaire, who seems to be living off the elixir of life and who has a history of making poor hiring decisions, at the head of the franchise, what awaits Chicago in the second half of this decade? There are four fates for the Sox.

The Sox continue to finish at the bottom of the AL Central with no clear path forward.
Of all four options, this is the most realistic. General manager Chris Getz continues to assemble a team of waiver-wire pickups with a few young but promising players filling in the gaps. Although it’s too early to say that players like Miguel Vargas and Brooks Baldwin won’t bloom into solid roster fixtures later this year or in subsequent years, it’s hard to see them blossoming with comparatively weak veteran mentorship.

If the budget doesn’t change, the Sox may be in purgatory longer.

The Sox regress to the point of having to start another rebuild.
Seeing the Sox fail so rapidly at this rebuild is less realistic, but the Sox have clearly shown that they can and will defy expectations. Seeing how top position player prospect in the farm system Colson Montgomery is faring in Triple-A, the Sox might be in for high prospect turnover. Chicago is familiar with failed rebuilds, and they may need to start their third rebuild in 15 years on the off-chance that their Top 10 prospects sink instead of swim.

Jerry sells the team, but they move out of Chicago.
Unfortunately, this scenario could still be in the cards. Regardless of how well the Sox play, Reinsdorf’s refusal to sell Ishbia the majority stake in the team could be because he’s holding out hope that he’ll get a bigger and better offer from someone who wants to move the team to another city. The Rate Field lease runs through 2030, but after that, there’s no guarantee that the Sox stay in the city. Between The 78, Arlington Heights, and Nashville, it’s widely speculated that the Sox won’t continue to play on the South Side much longer.

While tragic and heartbreaking, Reinsdorf doesn’t care about the Sox’s history in the league, or Chicago — he cares about money. If offered more than the $2 billion Forbes currently evaluates as the franchise’s value, Reinsdorf will probably take the offer even in the best of health.

The Sox become a playoff-caliber team.
Honestly, the chances of the Sox becoming a winning team are slim. Although new director of hitting Ryan Fuller, director of pitching Brian Bannister and manager Will Venable are helping this team elevate their game, it’s hard to fully buy into a GM who couldn’t develop the club’s talent during the first rebuild.