Friday, September 18, 2026

Big Cat: Wisconsin NIL, Barstool and Bears

Barstool Sports has gone from getting laughed out of LA pitch meetings to landing deals with Netflix and Fox Sports in the span of a decade. Dan Big Cat Katz has been there for all of it, and Baker Machado gets into exactly how Barstool evolved from a scrappy independent operation to a content engine that the biggest names in streaming are now coming to them to work with. The Wisconsin NIL situation has reportedly cost Madison up to $68 million in game day spending, and Big Cat has been trying to get involved for years.

He also started a coffee company named after his rescue dog that has donated nearly a quarter million dollars to pet adoption, and is now putting a hundred percent of ready to drink can profits toward funding a thousand pet adoptions nationwide. Pat McAfee, Alex Cooper, Will Compton: Barstool has launched some of the biggest independent sports media careers in the business.

Baker asks what it is about Barstool that keeps producing breakout talent, what the future looks like for Big Cat personally, and where Diana Russini fits into the independent media landscape after leaving The Athletic. Plus his honest take on the Bears potentially moving to Indiana.

Matt Iseman takes viewers beyond the scoreboard, inside the deals, and face-to-face with the personalities shaping sports.

Find Your Local Channel
Up Next

Learfield CEO on $40M Football Rosters, Jersey Patch Boom and Changes in..

Learfield CEO Cole Gahagan on NIL spending, jersey patches and college sports…
September 18, 2026

Mike Tirico on Michael Jordan, Pat McAfee, and Sports Media Landscape

Mike Tirico discusses Michael Jordan’s one season on NBA on NBC.
September 17, 2026

How an MLB Lockout Could Benefit the Savannah Bananas

Jackson Olson talks about the money behind the Savannah Bananas.
September 17, 2026