Now It's Legal with Jim Cavale

In Part Two of Now It’s Legal’s conversation with DeMaurice Smith, the focus shifts from the NFL to college athletics and the structural failures now playing out in real time. Drawing on his experience leading the NFLPA through multiple collective bargaining agreements, Smith explains why college sports are facing unprecedented instability: a lack of accountability, no collective bargaining framework, fragmented leadership and decision-making driven by emotion rather than rational business strategy.

In the 2026 season premiere of Now It’s Legal, host Jim Cavale and Athletes.org co-founder Brandon Copeland sit down with former NFL Players Association Executive Director DeMaurice “De” Smith, who led the NFLPA from 2009–2023. The conversation traces Smith’s unexpected path to union leadership, the motivations behind his book Turf Wars and the existential battle between NFL players and league ownership that culminated in the landmark 2011 Collective Bargaining Agreement.

In this week’s episode of Now It’s Legal, Jim Cavale sits down with Chris Ogden, General Manager of Texas Men’s Basketball, to unpack the complexities of building a competitive roster in the modern era of college sports. Ogden shares how his role as part recruiter, part negotiator, part strategist, has rapidly evolved amidst a chaotic landscape of NIL, the transfer portal and the House settlement. He explains how retention, culture, fit and long-term development must now be balanced with real-time market pressures and limited structure. Despite the volatility, Ogden advocates for standardized contracts, shared rules and a sustainable model for athletes and programs alike.

In this episode of Now It’s Legal, Jim Cavale sits down with UNC Athletic Director Bubba Cunningham to discuss the future of college athletics amid growing legal, economic and structural challenges. Cunningham shares insights on his planned transition from the AD role and the strategic decision to bring in Steve Newmark, a professional with broad business experience. The conversation dives deep into the evolving economic model in college sports, emphasizing the urgent need for enforceable rules, potential for collective bargaining and the consequences of inaction, including the loss of Olympic sports and further institutional disruption. In this episode, Cunningham advocates for a realistic, measured path forward all while highlighting the importance of leadership, collaboration and fresh perspectives in solving the challenges facing college athletics today.

Mark Byington is currently the head coach of the Vanderbilt University men’s basketball team. Prior to this role, he was the head coach at James Madison University, leading the team to its most successful four-season run in more than 30 years. From 2013-2020, Mark was the head coach at Georgia Southern, achieving three-consecutive 20-win seasons. Before becoming a head coach, he was an assistant coach at Virginia Tech and the College of Charleston.

Mark joins Now It’s Legal to discuss his current role as the head coach of the Vanderbilt University men’s basketball team, and his experience reconstructing the team through the NCAA transfer portal during his first season.
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About Now It's Legal   In July 2021, NIL forever changed the trajectory of college athletics. It’s been a long time coming as the NCAA has long needed changes like NIL, the transfer portal, revenue sharing and other benefits for college athletes.   We introduce to you the Now It’s Legal podcast. Join us as we discuss the industry that holds the hearts of millions of fans who want to understand where its trajectory is heading. We are talking to those who are invested in and affected by NIL including: Former and current college athletes, presidents and head coaches, broadcasters and media personalities, investors and more. This is just the beginning of NIL and what it means for the future of college athletics.        

Host Jim Cavale is a former college athlete and entrepreneur who has become an advocate for young athletes across the country. In 2017, he created the INFLCR app that allowed athletes to build their brand on social media, and in 2021, evolved into the NIL management technology for more than 100,000 athletes across 200 college athletic programs. INFLCR has since been acquired by sports tech titan, Teamworks.        

In 2023, Jim founded Athletes.org which which is the players association for college athletes to negotiate the best terms for their college athletics experience. AO provides its member athletes with a free membership, empowering them with a voice, on demand support, and group licensing income in the same ways that professional league associations do for their member athletes.        

Tune in to a new episode on Wednesdays this summer and join in on the conversation on Instagram with @nowitslegalpod and @jimcavale.

Andy Kennedy is currently the head coach of the University of Alabama Birmingham men’s basketball team, leading them to two March Madness appearances. His coaching career began as an assistant at the University of South Alabama from 1994-1995. Andy was also an assistant coach at UAB and the University of Cincinnati before becoming Cincinnati’s interim head coach. From 2006-2018, Andy was the head coach of the University of Mississippi men’s basketball team.  Andy joins Now It’s Legal to discuss his coaching career at UAB and Ole Miss, and his thoughts on the current landscape of college athletics.  
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About Now It's Legal   
In July 2021, NIL forever changed the trajectory of college athletics. It’s been a long time coming as the NCAA has long needed changes like NIL, the transfer portal, revenue sharing and other benefits for college athletes.   We introduce to you the Now It’s Legal podcast. Join us as we discuss the industry that holds the hearts of millions of fans who want to understand where its trajectory is heading. We are talking to those who are invested in and affected by NIL including: Former and current college athletes, presidents and head coaches, broadcasters and media personalities, investors and more. This is just the beginning of NIL and what it means for the future of college athletics.        

Host Jim Cavale is a former college athlete and entrepreneur who has become an advocate for young athletes across the country. In 2017, he created the INFLCR app that allowed athletes to build their brand on social media, and in 2021, evolved into the NIL management technology for more than 100,000 athletes across 200 college athletic programs. INFLCR has since been acquired by sports tech titan, Teamworks.        

In 2023, Jim founded Athletes.org which which is the players association for college athletes to negotiate the best terms for their college athletics experience. AO provides its member athletes with a free membership, empowering them with a voice, on demand support, and group licensing income in the same ways that professional league associations do for their member athletes.        

Tune in to a new episode on Wednesdays this summer and join in on the conversation on Instagram with @nowitslegalpod and @jimcavale.

Josh Pastner is currently the head coach of the University of Nevada, Las Vegas men’s basketball team. He played on the 1997 National Championship team at the University of Arizona before becoming their assistant coach from 2002-2008. During the 2008-2009 season, Josh was an assistant coach and recruiting coordinator at the University of Memphis before taking the role of head coach of the men’s basketball team until 2016. He is the second winningest head coach for the first seven seasons in the history of Tigers basketball. Josh was the head coach of Georgia Tech from 2016-2023.

Josh joins Now It’s Legal to discuss his involvement with the transfer portal at UNLV, adapting to and embracing the ever-changing landscape of college basketball.
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About Now It's Legal  

In July 2021, NIL forever changed the trajectory of college athletics. It’s been a long time coming as the NCAA has long needed changes like NIL, the transfer portal, revenue sharing and other benefits for college athletes.      We introduce to you the Now It’s Legal podcast. Join us as we discuss the industry that holds the hearts of millions of fans who want to understand where its trajectory is heading. We are talking to those who are invested in and affected by NIL including: Former and current college athletes, presidents and head coaches, broadcasters and media personalities, investors and more. This is just the beginning of NIL and what it means for the future of college athletics.      

Host Jim Cavale is a former college athlete and entrepreneur who has become an advocate for young athletes across the country. In 2017, he created the INFLCR app that allowed athletes to build their brand on social media, and in 2021, evolved into the NIL management technology for more than 100,000 athletes across 200 college athletic programs. INFLCR has since been acquired by sports tech titan, Teamworks.      

In 2023, Jim founded Athletes.org which which is the players association for college athletes to negotiate the best terms for their college athletics experience. AO provides its member athletes with a free membership, empowering them with a voice, on demand support, and group licensing income in the same ways that professional league associations do for their member athletes.      

Tune in to a new episode on Wednesdays this summer and join in on the conversation on Instagram with @nowitslegalpod and @jimcavale.

John Talty is an award-winning national college sports reporter for CBS Sports. He is the Wall Street Journal best-selling author of his book, "The Leadership Secrets of Nick Saban: How Alabama's Coach Became the Greatest Ever." Armen Keteyian is an 11-time Emmy award-winning television journalist, previously a CBS News correspondent and a Sports Illustrated writer-reporter. John and Armen are co-authors of their book, “The Price: What It Takes to Win in College Football’s Era of Chaos.”

John and Armen join Now It’s Legal to discuss their co-authored book that includes an in-depth dive into the “Wild West” of college athletics: NIL, endorsements, the transfer portal and the effect this chaos has on premier college coaches and athletes.
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About Now It's Legal
In July 2021, NIL forever changed the trajectory of college athletics. It’s been a long time coming as the NCAA has long needed changes like NIL, the transfer portal, revenue sharing and other benefits for college athletes.    

We introduce to you the Now It’s Legal podcast. Join us as we discuss the industry that holds the hearts of millions of fans who want to understand where its trajectory is heading. We are talking to those who are invested in and affected by NIL including: Former and current college athletes, presidents and head coaches, broadcasters and media personalities, investors and more. This is just the beginning of NIL and what it means for the future of college athletics.    

Host Jim Cavale is a former college athlete and entrepreneur who has become an advocate for young athletes across the country. In 2017, he created the INFLCR app that allowed athletes to build their brand on social media, and in 2021, evolved into the NIL management technology for more than 100,000 athletes across 200 college athletic programs. INFLCR has since been acquired by sports tech titan, Teamworks.    

In 2023, Jim founded Athletes.org which which is the players association for college athletes to negotiate the best terms for their college athletics experience. AO provides its member athletes with a free membership, empowering them with a voice, on demand support, and group licensing income in the same ways that professional league associations do for their member athletes.    

Tune in to a new episode on Wednesdays this summer and join in on the conversation on Instagram with @nowitslegalpod and @jimcavale.

Diego Pavia is currently a quarterback for the Vanderbilt University Commodores. He previously played for New Mexico State, leading them to a 10-5 record which included beating Auburn. In December 2023, Diego entered the transfer portal before transferring to Vanderbilt in January 2024. He led the Commodores to the Birmingham Bowl, their first bowl game since 2018, where he was named MVP. Diego also led the team to an upset victory against Alabama — the program's first win over Alabama since 1984.  

Diego joins Now It’s Legal to discuss winning an injunction against the NCAA, allowing him to enter the transfer portal and play in 2025.

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About Now It's Legal
In July 2021, NIL forever changed the trajectory of college athletics. It’s been a long time coming as the NCAA has long needed changes like NIL, the transfer portal, revenue sharing and other benefits for college athletes.    

We introduce to you the Now It’s Legal podcast. Join us as we discuss the industry that holds the hearts of millions of fans who want to understand where its trajectory is heading. We are talking to those who are invested in and affected by NIL including: Former and current college athletes, presidents and head coaches, broadcasters and media personalities, investors and more. This is just the beginning of NIL and what it means for the future of college athletics.    

Host Jim Cavale is a former college athlete and entrepreneur who has become an advocate for young athletes across the country. In 2017, he created the INFLCR app that allowed athletes to build their brand on social media, and in 2021, evolved into the NIL management technology for more than 100,000 athletes across 200 college athletic programs. INFLCR has since been acquired by sports tech titan, Teamworks.    

In 2023, Jim founded Athletes.org which which is the players association for college athletes to negotiate the best terms for their college athletics experience. AO provides its member athletes with a free membership, empowering them with a voice, on demand support, and group licensing income in the same ways that professional league associations do for their member athletes.    

Tune in to a new episode on Wednesdays this spring and join in on the conversation on Instagram with @nowitslegalpod and @jimcavale.

Johnny Manziel is a former NFL quarterback for the Cleveland Browns. Out of high school, he was nationally recruited as a redshirt freshman for Texas A&M. He broke numerous NCAA Division I FBS and SEC records, including being the first freshman and fifth player in NCAA history to pass for 3,000 yards and rush for 1,000 yards in one season, and was the first freshman to win the Heisman Trophy, the Manning Award and the Davey O'Brien Award. Johnny was selected by the Browns in the 2014 NFL draft as the 22nd overall pick, playing for two seasons.  Johnny joins Now It’s Legal to discuss his nationally recognized and record-breaking college football career and his perspective of playing in the NCCA.  
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About Now It's Legal  
In July 2021, NIL forever changed the trajectory of college athletics. It’s been a long time coming as the NCAA has long needed changes like NIL, the transfer portal, revenue sharing and other benefits for college athletes.      
We introduce to you the Now It’s Legal podcast. Join us as we discuss the industry that holds the hearts of millions of fans who want to understand where its trajectory is heading. We are talking to those who are invested in and affected by NIL including: Former and current college athletes, presidents and head coaches, broadcasters and media personalities, investors and more. This is just the beginning of NIL and what it means for the future of college athletics.      

Host Jim Cavale is a former college athlete and entrepreneur who has become an advocate for young athletes across the country. In 2017, he created the INFLCR app that allowed athletes to build their brand on social media, and in 2021, evolved into the NIL management technology for more than 100,000 athletes across 200 college athletic programs. INFLCR has since been acquired by sports tech titan, Teamworks.      

In 2023, Jim founded Athletes.org which which is the players association for college athletes to negotiate the best terms for their college athletics experience. AO provides its member athletes with a free membership, empowering them with a voice, on demand support, and group licensing income in the same ways that professional league associations do for their member athletes.      

Tune in to a new episode on Wednesdays this fall and join in on the conversation on Instagram with @nowitslegalpod and @jimcavale.