When I first read about Jerry Reinsdorf’s long-term succession deal involving the Chicago White Sox, I didn’t expect it to be such a compelling lesson in estate planning. But the interesting structure and flexibility behind the deal really stuck with me.
Reinsdorf, who has owned the White Sox since the 1980s, recently set up a unique transition with billionaire investor Justin Ishbia. It’s not going to be an immediate change of ownership. Rather, Ishbia will start by contributing capital as a limited partner over the next couple of years. After that, control will begin to shift gradually, with full ownership potentially taking place after the 2034 season.
If you stop and think about it, that approach makes a lot of sense. Whether you're passing on a business, a portfolio, or a complex estate - transitions tend to go more smoothly when they happen over time.
The deal includes options to sell, options to buy, and a timeline that helps preserve the organization’s stability. This is about more than just control - it’s also about timing, taxation, and preserving legacy.
Similarly, when we work with clients on estate or succession strategies (especially business owners or families with multi-generational wealth), we focus on many of the same principles.
For example:
• How can the plan reduce future tax burdens?
• Should the transition be structured in stages to limit disruption?
• Are gifts or trusts better suited to your goals?
• And how can we ensure that everyone involved understands their role?
These aren’t just questions for billionaires. They matter to anyone who has spent years building something meaningful and wants to make sure it continues in the right way.
If this story made you think about your own long-term plans, like it did for me, I’d be happy to have a conversation. It’s never too early to start thinking about the legacy of what you’ve worked so hard to build.