Dave Checketts, veteran sports executive and investor, joins Portfolio Players for a conversation on ownership, expansion, and the evolving economics of global sports. Checketts breaks down: • Why scarcity is the single biggest driver of franchise value • The investment strategy behind his fund and why cash flow matters • Michael Jordan/Knicks stories, lessons from Utah & New York • The realities of launching new leagues and why venture capital often stays away • His perspective on MLS growth, global soccer, and media rights • The rise of NIL and why education still needs to be prioritized • Expansion opportunities across MLB, the NBA, and beyond This episode of Portfolio Players, presented by @etrade_frommorganstanley, explores how experienced operators think about ownership, capital allocation, and the long-term value of sports franchises. Chapters: 1:00 - Utah Presidency 2:50 - Las Vegas Expansion 3:30 - Seattle Expansion 4:30 - Vegas Expansion Continued 5:00 - Kareem Breaking Points Record + David Stern Story 7:00 - Influx of Gambling, Good or Bad? 8:45 - Prediction Markets, League Adoption 10:00 - Knicks/Brooklyn Story 11:00 - Attending Unrivaled, as a Veritable Business 13:10 - Investing in Sports Startups 14:25 - MLS Investment, MLS vs. PL, Apple TV Deal 17:00 - Knicks & Bulls Story, MJ non-sellout 19:30 - 1990s NBA 23:00 - Investment Strategy Looking Ahead, Golf + CFB 24:30 - PE Money in College, Collective Bargaining? 26:30 - Financial Literacy In Sports 28:15 - Golf Equipment Boom, Investment Opportunities 29:15 - MLB, Utah Expansion? NBA Story 33:30 - Ownership Competition across Leagues, NFL Rules 35:15 - Family Success Portfolio Players is Front Office Sports’s original series exploring the deals, capital, and decision-makers shaping the future of sports business. Subscribe for more conversations with the industry’s top builders and investors.