For nearly half a century, Jerry Reinsdorf has presided over the Chicago White Sox — a tenure marked by championship highs, gut-wrenching lows, and no shortage of Chicago-style controversy. But now, with a deal quietly structured behind the scenes, the first true framework of succession has finally been laid. Enter Justin Ishbia, the billionaire investor and Chicago native, who has long admired the game and the city. This week, the White Sox formally announced that Ishbia will begin increasing his stake, with an option to take full control of the club in the years ahead.

It’s a transaction years in the making. Originally pursuing ownership opportunities with the Minnesota Twins, Ishbia found himself redirected to Chicago when the Reinsdorfs approached him. What began as a conversation about increasing a minority stake has now evolved into something much larger: the blueprint for eventual control of one of baseball’s most iconic — and tortured — franchises. The deal echoes the structure used in Cleveland just a few years prior, with a long runway that stretches deep into the next decade.

In the meantime, Reinsdorf, ever the power broker, remains firmly at the helm. At 88 years old, he retains full operational control, even as the Sox endure one of the most painful stretches in their history. With a franchise-worst 121 losses last year and another bleak season unfolding, the backdrop is hardly one of triumph. But as always in baseball, the next chapter is never far away, and Ishbia’s arrival hints at sweeping change — in the boardroom, and potentially, on the diamond.

Justin Ishbia brings with him not only deep pockets but a family of sports executives familiar with the modern business of professional franchises. His brother Mat controls the NBA’s Phoenix Suns and WNBA’s Mercury, while his father Jeff joins the venture as well. Together, the Ishbias bring a corporate sophistication that could help reimagine how the White Sox operate — from player development to stadium negotiations to front office strategy — all under the watchful eye of Chicago’s famously passionate fan base.

Reinsdorf, who famously purchased the White Sox in 1981 for just $19 million, now presides over a franchise with a valuation approaching $2 billion. Many of the original minority investors have quietly cashed out, while others have remained in place, hoping the eventual Ishbia-led era might finally bring the consistency and ambition that has long eluded the South Side faithful. As always in Chicago, hope is both fragile and eternal.

​And looming behind it all remains the stadium issue — an unresolved subplot that will shape the franchise's future almost as much as ownership itself. Reinsdorf’s public efforts to secure a new taxpayer-funded stadium have yet to yield fruit, while alternative sites — like the South Loop’s 78 development — remain tangled in politics, real estate, and competing sports interests. One chapter nears its conclusion, but as Ishbia patiently waits for his inning, the most fascinating part of this story may still be ahead.