The Bill Simmons Podcast

The Bleakest NBA Team Situations (Next 5 Years) With Ryen Russillo

133 snips
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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INSIGHT

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.
INSIGHT

Why the Chicago Bulls Have the Bleakest NBA Future

Bill Simmons and Ryen Russillo dive deep into NBA team roster situations and agree that the Chicago Bulls face the bleakest outlook in the Eastern Conference for the next five years. Simmons highlights the Bulls' lack of star power and questionable ownership, stating, "This has been a criminally misused asset since Jordan left," and "I just don't know what this team is other than a team that's going to go 40 and 42 every year." Despite having some young players and draft picks, their contracts and overall team construction offer little hope for contention.

The duo notes that the Bulls have around $85 million in expirings, but no clear path to elevate their status to a playoff contender. Simmons laments that the Bulls' tremendous fan base and Chicago market have been squandered by steady underinvestment and poor decision-making, making it a missed opportunity. The discussion underscores how ownership and front office mismanagement severely hamper a team's potential, regardless of its market size or history.

INSIGHT

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.
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