
Legendary NBA Exec Dave Checketts Dishes on Michael Jordan, David Stern, Running the Knicks & More
5/14/2026
0:00
44:05
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
hapters:
1:00 - UtahJazz 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
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