The Ryen Russillo Podcast – June 24, 2025

Episode: Simons-Holiday Trade Thoughts and the Value of a Top-10 Pick. Plus, Kevin Boyle on the Draft

1. Trade Analysis: Drew Holiday to Portland Trailblazers for Anthony Simons

The episode kicks off with a deep dive into a significant NBA offseason move: Drew Holiday of the Boston Celtics was traded to the Portland Trailblazers in exchange for Anthony Simons. Ryen Russillo breaks down the intricacies of the deal, highlighting the financial and strategic motivations behind it.

Russillo [09:00]: "Drew is going to pick that one up. So you're looking at paying him $37.2 million at 37 years old when he didn't look great this past year."

2. Financial Implications: Navigating the Second Apron

Russillo explains the Celtics' maneuver to lower their tax bill by trading Holiday's hefty contract for Simons' more manageable deal. This move places the Celtics over the second apron, introducing a slew of salary cap restrictions.

Russillo [12:30]: "This deal alone saves ownership $40 million of tax savings where the Celtics are now $18 million over the second apron."

He elaborates on the second apron rules, emphasizing the limitations it imposes on the Celtics' future transactions, including restricted trade flexibility and the inability to use trade exceptions.

3. Potential Future Moves: Porzingis and Roster Adjustments

The conversation shifts to fan speculation about possible future trades, notably concerning Kristaps Porzingis. Russillo contemplates whether the Celtics might leverage the Porzingis situation to further alleviate their salary cap constraints.

Russillo [16:45]: "There's a Pozingus trade out there... he's an expiring $30 million deal... It's about how much they can lower that $18 million number over the second apron."

4. Celtics' Roster and Future Strategies

Russillo assesses the broader implications for the Celtics' roster, including the potential adjustments around key players like Jaylen Brown and the challenges posed by the team's current financial state.

Russillo [21:10]: "What are the Celtics really capable of this off season? It's worth at least spending a couple minutes on that."

5. Top 10 Draft Picks Trends: Stability vs. Movement

Transitioning to draft analysis, Russillo reviews the stability of top 10 picks over recent years, noting a trend where a minority remain with their drafting teams.

Russillo [28:00]: "If we really go through 17, 21, 6 year average, three and a half picks of the top 10 picks stay with the team that brought them in last draft."

6. Interview with Kevin Boyle: Insights on His Elite Draft Class

A pivotal segment of the episode features an interview with Kevin Boyle, the acclaimed head coach at Spire Academy in Ohio. Formerly at Mount Vernon, Boyle has a storied history of coaching top-tier high school talent.

Key Discussion Points:

• Elite Talent Development: Boyle discusses his current draft class, which boasts four first-rounders, including Cooper Flag, Liam, Asa, and Derek Queen.

  Boyle [20:28]: "Liam, I think worked like hell to, to first to be a guy that I think some people question, is he a second round pick?"

• Coaching Philosophy: Emphasizing transparency, Boyle advises his players on adapting to NBA roles, whether as primary scorers or impactful role players.

  Boyle [21:56]: "We try to be very honest to them and also to tell them how many guys that are ranked really high are not playing."

• Training Regimen: Highlighting the rigorous practice routines, Boyle ensures his athletes are well-prepared for the demands of collegiate and professional basketball.

  Boyle [23:24]: "Our thing is we don't want them to go to a college and then to say practice is harder in college."

• Player Development: Discussing individual players, Boyle provides insights into their strengths and potential NBA roles, forecasting bright futures for his protégés.

  Boyle [26:34]: "Cooper is, to me, he's going to probably be a 19, 7 and 7, 22, 10 and 8, and kind of like Kate Cunningham, who we had all of a sudden, like, he's averaging 27, 11 and 9, you know, and just incredibly impactful."

7. Conclusion and Final Thoughts

The episode wraps up with Russillo summarizing the key takeaways from the trade analysis and the insights shared by Kevin Boyle. The overarching theme highlights the interplay between financial strategy and talent management within the NBA, underscored by the promising trajectory of emerging high school stars.

Russillo [82:29]: "Because when the pressure dials up, you have a teammate who can help."

Notable Quotes:

• Russillo on the Trade's Financial Impact [12:35]: "This deal alone saves ownership $40 million of tax savings..."

• Boyle on Player Roles [21:56]: "Steph Curry's a role player. His role is to get 30."

• Russillo on Draft Pick Trends [28:00]: "Three and a half picks of the top 10 picks stay with the team that brought them in last draft."

• Boyle on Coaching Philosophy [21:56]: "We try to be very honest to them and also to tell them how many guys that are ranked really high are not playing."

Final Thoughts

This episode of The Ryen Russillo Podcast offers a comprehensive analysis of recent NBA trades, the financial strategies of top teams like the Boston Celtics, and an exclusive look into the development of future NBA stars through the lens of Kevin Boyle’s coaching expertise. Whether you're a die-hard basketball fan or a casual listener, this episode provides valuable insights into the current landscape of professional basketball and the emerging talents poised to shape its future.