The Succession Wave
Three of baseball’s most established front offices went through leadership changes in quick succession, and each one played out differently. On June 24, 2026, the Cardenales de San Luis promoted Bill DeWitt III to CEO while his father, Bill DeWitt Jr., remained as principal owner. That same year, on February 12, 2026, the Rojos de Cincinnati made their first change in 20 years when Phil Castellini took over for his father, Bob Castellini. And in Cleveland, the Guardianes de Cleveland faced an unplanned transition when owner Larry Dolan died on February 23, 2025, at age 94, with David Blitzer holding an option to take control around 2028.
These weren’t simultaneous announcements or coordinated moves. They happened over months, each one carrying a different story about how power and responsibility shift in a family business worth hundreds of millions of dollars. Together, they’re reshaping the ownership landscape at a level most fans never see.
Three Different Paths
The Cardenales de San Luis transition was the cleanest handoff. Bill DeWitt III stepped into the CEO role while his father stayed involved, a structure that keeps continuity while introducing new leadership. The Rojos de Cincinnati saw Phil Castellini step into a role his father held for two decades—a change that carried the weight of 20 years of operations under one person.
Cleveland’s situation was the most uncertain. When Larry Dolan passed away, the team didn’t automatically transfer to a new owner. Instead, David Blitzer, who bought a 25% stake in 2022, has a path to majority control through a prearranged option at a set price, with that transition expected around 2028. That structure means the Guardianes de Cleveland will operate under interim leadership while the clock runs toward a predetermined date.
Why This Matters Now
These transitions matter because ownership decides payroll, trades, stadium investment, and ticket prices. A new owner or CEO can shift a team’s entire direction. When a 30-year run ends in St. Louis or a 20-year tenure concludes in Cincinnati, the people making those decisions change. The philosophies can change. The patience with losing seasons can change.
For fans, these handoffs aren’t abstract. They affect whether your team spends to win now or builds for five years from now. They affect whether the front office stays stable or gets completely remade. They affect whether a new owner decides to invest in the ballpark or hold back.
The timing also matters. All three teams are navigating this transition while the sport itself is changing—salary structures are evolving, free agency works differently, and the pressure to compete in a 30-team league is constant. A new leader stepping in has to learn the current landscape while inheriting whatever decisions the previous leadership made.
What’s striking is that none of these transitions happened the same way. Bill DeWitt III didn’t inherit the team outright; he inherited a role. Phil Castellini took over a family operation. David Blitzer is waiting for a predetermined moment to take full control. Each path reflects different family structures, different business plans, and different ways of thinking about succession.
The next few seasons will show whether these transitions were smooth or rocky. Bill DeWitt III has to prove he can run the Cardenales de San Luis at the same level his father did. Phil Castellini has to establish his own identity separate from his father’s two decades. David Blitzer has to keep the Guardianes de Cleveland competitive while waiting for his option to trigger.
This is the quiet drama of baseball ownership—not the trades or the free agents, but the moment when power passes from one generation to the next. It happens rarely, it happens differently every time, and it reshapes how a franchise operates for years to come.
The number: In less than two years, three MLB teams—the Cardenales de San Luis, Rojos de Cincinnati, and Guardianes de Cleveland—all underwent ownership or leadership transitions, each following a completely different path.
Ownership data verified as of 2026-08-12.
