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Legendary NBA Exec Dishes on Michael Jordan, David Stern, Knicks & More
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.
Soccer legend Gareth Bale shares why he looks to Steph Curry when preparing for life beyond the game
I look at Steph Curry as a great example… you can see that he's really kind of put in the work in to do business.” Soccer legend ...
Gareth Bale on MLS vs Premier League, Retirement & Buying Cardiff City
Five-time Champions League winner Gareth Bale kicks off this season of Portfolio Players and shares how lessons from past ...
Gareth Bale on MLS vs Premier League, Retirement & Buying Cardiff City
In Season 2 Episode 1 of Portfolio Players presented by E*TRADE from Morgan Stanley, Gareth Bale reflects on his playing ...
TNT Says Goodbye to the NBA | How Will Barkley and Shaq Fit in at ESPN?
After 35 years, TNT has officially bid adieu to the NBA, with NBC and Amazon Prime Video taking over the network's coverage ...
How Shaq Created a $100m+ Business Empire
Discover how Shaquille O'Neal transformed from a $300 million NBA superstar into a $500 million business mogul with smart ...
How An Angry Fan Changed The Trajectory of Shaq's Career 👟
After an interaction with an angry fan, Shaquille O'Neal turned down a $40 million Reebok deal to create a new brand with ...
Michael Jordan is Giving Away A Set of Every Jordan Sneaker Ever Made 👟
Michael Jordan will give one fan a pair of every Jordan sneaker ever made — if they buy his abandoned Chicago mansion.
Highlights
Former MLB CFO On What’s Driving Team Valuations and Ownership Trends
What does it take to protect the long-term value of a sports league? In Episode 9 of Portfolio Players, Jonathan Mariner—former ...
MLB’s Post-Pitch Clock Boom Continues
MLB had its best-attended weekend in over a decade, while its local broadcasting future gets hashed out in court. Meanwhile ...
What's Holding up the A's New Vegas Stadium?
The Oakland A's remain on the hunt for funding to build their Las Vegas stadium, but that, and many of the basic details of their ...
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