Dave Checketts has spent nearly two decades at the highest levels of professional sports, and in a revealing new interview, the former NBA executive is sharing the playbook that shaped his career. From running the New York Knicks and Utah Jazz to investing across multiple leagues, Checketts offers a masterclass in sports business strategy.

In the latest episode of Portfolio Players, presented by E*TRADE from Morgan Stanley, Checketts breaks down why scarcity remains the ultimate driver of franchise value. He points to the NFL and NBA as prime examples—limited supply, massive demand, and a business model that rewards patience over flash. "The teams that win long-term are the ones that treat their assets like gold," he explains.

But the conversation isn't all balance sheets. Checketts also shares unforgettable stories from his time in the trenches, including behind-the-scenes moments with Michael Jordan during the Knicks-Jazz rivalry. He reflects on the unique challenges of building in markets like Las Vegas and Utah, and why venture capital has often struck out when trying to launch startup leagues from scratch.

From NIL and education reform to future expansion in MLB and shifting ownership dynamics, Checketts provides a blueprint for how seasoned operators evaluate risk and build enduring value in sports. Whether you're a die-hard fan or an aspiring executive, his insights are a reminder that in the game of sports business, the best investments are often the ones you hold onto the longest.