The Bill Simmons Podcast The Bleakest NBA Team Situations (Next 5 Years) With Ryen Russillo
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Jul 7, 2025 
Ryen Russillo, an NBA analyst and podcast host, joins for a lively discussion about the most precarious roster situations in the league. They explore the aftermath of free agency, dissecting the challenges facing teams like the Bulls and Raptors. The conversation dives into LeBron’s uncertain future with the Lakers and evaluates DeAndre Ayton's fit in Los Angeles. With a mix of humor and insights, Ryen and Bill break down the financial strategies that may reshape NBA dynamics in the coming years.
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Toronto's Costly Roster Rigidity
- Toronto's top five players have pricey contracts with questionable health and impact.
- This makes flexibility minimal despite having relatively talented players like Scottie Barnes and Brandon Ingram.
Chicago's Bleak Roster and Ownership
- Chicago Bulls lack a clear star and have many expiring contracts.
- Ownership has shown unwillingness to invest, limiting future prospects.
Chicago's Untapped Franchise Potential
- Chicago is an undervalued asset with a passionate fan base and enormous market potential.
- Mismanagement has led to wasted opportunity since Jordan's departure.