Tom Ricketts: Tradition and Transformation Leading a Legacy Team into the Future

In this episode of On Stage, Tom Ricketts, Chairman of the Chicago Cubs, joins Joe Leccese, Chairman Emeritus of Proskauer, for a wide-ranging conversation about stewardship, leadership, and the evolving business of baseball. Recorded on November 19, 2025, at SBJ Dealmakers Conference, the discussion explores how Ricketts balances the weight of tradition that comes with owning one of the most iconic franchises in sports while positioning the Cubs for long-term success in a rapidly changing industry.
Key themes include:

• Owning a Legacy Franchise: What it means to lead a century-old team with a deeply rooted fan base and global profile.
• Long-Term Vision: How the Cubs think about competitive windows, financial discipline, and sustainable success.
• Business of Baseball: Ricketts’ perspective on league economics, media evolution, and the forces reshaping MLB.
• Leadership & Governance: Lessons from navigating change, aligning stakeholders, and making decisions with generational impact.
• Wrigley Field & the Fan Experience: How the Cubs continue to evolve their ballpark and surrounding ecosystem while honoring tradition.

It’s an insightful conversation with one of sports’ most dynamic owners — offering perspective on how legacy organizations adapt, endure, and evolve.

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