The Chicago White Sox Will be Good by 2028

Jerry Reinsdorf is thinking about selling the team. Which may then move to Nashville. Executive Vice President Kenny Williams and General Manager Rick Hahn have been fired; the first time the White Sox have ever fired team personnel mid-season. While Manager Pedro Grifol is currently still employed, his status is being examined by Tony La Russa, most probable future GM Chris Getz, and future front office executive Dayton Moore. That would be the former manager who got the job because he is friends with the owner and subsequently ran the team into the ground, the current Assistant General Manager who has presided over a number of controversies while in charge of the terrible Sox minor league system, and the former GM of the Royals who organized an anti-porn seminar for the team and championed a convicted child molester.

It’s one step forward and who knows how many steps back for the White Sox. Reinsdorf may sell the team, providing hope for a true refresh and rebuild of the franchise. Which could then relocate. The top two executives who oversaw the building of and ensuing collapse of the team were fired. Then effectively replaced by two people wholly unqualified for the jobs.

And also La Russa.

And the players don’t seem to care or take any responsibility.

But the White Sox will be good again in 2028.

Or at least thereabouts. 2028. Or thereabout. So about 5 years. Here’s a simple breakdown.

2023 – Obviously awful. Lost year. Everyone fired.

2024 – Rebuild. Just feels like it’s going to be another lost year while the team figures out what it’s going to do.

2025 – Rebuild, Year One redux. Start to turn the corner. Still bad, but hopeful.

2026 – Rebuild, Year Two.

2027 – Rebuild, Year Three. Maybe start thinking about being competitive.

2028 – Rebuild, Year Four. Competitive. Make the playoffs, even if just the Wild Card.

It’s the 2025 season which is the pivotal year/season. That will probably be the turning point for the White Sox organization. The year that the fortunes of the organization and the team really reach a critical mass that determines the future success or failure of the Chicago White Sox. Or Nashville White Sox. Whatever/wherever the team ends up. Because 2025 is most likely the year the White Sox gain new ownership. Because 2025 is most probabilistically the year Jerry Reinsdorf will die.

To be clear, that is not a desired outcome. But it is seemingly that event at which the team would be sold. In the past, Reinsdorf has said that his recommendation to his family is they sell the White Sox following his death. Which would be in 2025. At that time Jerry Reinsdorf would be 89 years old, which is the average lifespan for billionaires. And as Chicago fans have seen in the past, struggling franchises many times need a radical overhaul in order to change fortunes. Whether that be a change in ownership or at least an innovation in team operations. The White Sox under Reinsdorf, it feels like the former; again, without any hope of that event.

It was the sale of the Chicago Cubs to the Ricketts family which paved the way for all the future success of that team. The current promising direction, hopefully leading towards sustained future success of the Chicago Bears was preceded by a radical departure in team operations from the past team model. While the Chicago Bulls, also owned by Reinsdorf, have ostensibly altered their front office structure and how it operates in recent seasons, that structure is apparently still hobbled by restrictions placed upon it by ownership. And the Stanley Cup success of the Chicago Blackhawks following a decade of a quite moribund existence, was really only made possible by the death of owner Bill Wirtz.

While there is no empirical proof a change in team ownership leads to a greater probability of team success, anecdotally it feels like a positive precursor. What is undeniably true is that the White Sox need a change of direction, both for the team as well as how the organization is run, in order to win. And the direction of the current search for new leadership does not build confidence. Radical change requires a radical change in mindset and operation.

The Ricketts family bought the Cubs in 2009. The team made the playoffs in 2015 and won the World Series in 2016. The Bears brought in current team General Manager Ryan Poles in 2022, vastly altering the structure of the front office and team operations in the process. By the 2024-25 season, the Bears will hopefully be in contention for the NFL playoffs. And when Bill Wirtz died in 2007, his son Rocky assumed responsibility of team operations, ushering in an entirely new era of Blackhawks hockey. The ‘Hawks were in the playoffs in 2008-09, won the Stanley Cup in 2009-10, as well as 2 more in the next 5 years.

So that’s 6 years, hopefully 3 years, and 2 years, respectively, between a vast change in team ownership and/or team operations and team playoff success. Small sample size and it’s difficult to make sweeping declarations and lessons across different sports, but 3 to 4 years on average between the change and success. And 2028 would be 3 years after ownership change in this scenario. 2028 optimistically, maybe 2029 more realistically.

Although rather bleak, the death of Jerry Reinsdorf would appear to be the most likely path towards future team progress.

Here’s to 2025.