Hall of Famer Tracy McGrady is considered one of the best shooting guards to ever play the game of basketball. His post-playing career is one of a multifaceted businessperson. T-Mac is one of the lead studio analysts on NBC’s nostalgic return to NBA coverage. And in December 2024, Tracy and his cousin Vince Carter were among 10 limited partners who joined the Buffalo Bills ownership group. Oh, and he started his own league, Ones Basketball.

In this episode of The Deal, Alex and Jason sit down with Tracy to walk through his journey from the court to the boardroom. He shares how the Bills deal fulfilled one of his longtime goals and Alex and Tracy compare notes on lessons they’ve learned in the transition from athlete to owner. Tracy also explains how the 90s revolutionized the business of basketball, the joy of doing business alongside his cousin Vince and why he is going all-in on one-on-one.

You can also watch this interview on YouTube.

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Jess Pegula has spent her life around elite sports — both as one of the best tennis players in the world and as part of the family behind the Buffalo Bills and Buffalo Sabres. Beyond competing at the highest level, she’s become an influential voice in the future of professional tennis through her role as a player representative for the Women’s Tennis Association, giving her a rare window into both the business and competitive sides of the industry.

In this episode of The Deal, Alex Rodriguez and Jason Kelly sit down with Jess to talk about lobbying for change in professional tennis, balancing the interests of players and management, and what she’s learned from growing up around major sports franchises. Jess shares lessons from her parents Terry and Kim Pegula on leadership, team building and adapting to different personalities. She also discusses the unique culture of Buffalo sports and how her experiences in tennis and sports ownership have shaped the way she approaches business and competition.

You can also watch this interview on YouTube.

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Alan Waxman’s Sixth Street Partners has a deep conviction in sports. Over the past five years, Alan and his firm have taken a minority stake in teams in most major professional leagues, including: the Boston Celtics, the San Antonio Spurs, the San Francisco Giants and FC Barcelona. In 2024, Sixth Street became the first investment fund to take a controlling interest in an American pro team with the NWSL’s Bay FC. And as of September 2025, Sixth Street owns a 3% stake in one of the biggest names in sports- the New England Patriots.

In this episode of The Deal, Alex and Jason sit down with Alan live at Bloomberg Invest. Alan tells the story of getting the call from Robert Kraft and why Sixth Street is one of only a handful of PE firms approved to invest in the NFL. He also shares his view on international growth opportunities in the NBA, why a historic NWSL expansion fee paid off and how far away we are from institutional capital taking a controlling stake in an NFL or NBA team. Finally, Alex and Alan give their takes on how to “fix” professional baseball.

You can also watch this interview on YouTube.

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Baseball and softball are both having a moment. The 2025 Women’s College World Series was the most watched ever, with 2.4 million people tuning in to game 3. On the baseball side, almost 11 million people watched Venezuela beat the U.S. to take the 2026 World Baseball Classic title. The audience for both sports is growing, and LSU softball star and baseball media analyst AJ Andrews is one of their most enthusiastic ambassadors.

In this episode of The Deal, Alex Rodriguez and Jason Kelly talk to AJ about how the MLB must embrace player authenticity in order to flourish. She also shares how a conversation with ESPN’s Jessica Mendoza changed her career trajectory and why the future of softball lies in storytelling. Finally, AJ and Alex compare notes about the benefits of being an athlete turned broadcaster.

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Steve Young has created a playbook for so many athletes looking to make their way in business and spends a lot of his time paying it forward. HGGC, the private equity firm he started in 2007 with Rich Lawson, currently has an AUM above $10 billion. He also happens to be one of the best quarterbacks to ever play the game of football.

In this episode of The Deal, Alex Rodriguez and Jason Kelly hit the road to talk to Steve Young at his Palo Alto office. Steve shares why making a clean break from football was one of the best decisions he’s made in his career, why he considers himself “highly fireable” and how he built a fund with a spirit of abundance. He also shares some stories about Roger Staubach, Bill Walsh and his dad, Grit Young.

You can also watch this interview on YouTube.

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Kara Nortman bets big on women’s sports, and it’s paying off. She is the co-owner of Angel City FC, an NWSL team with a $335 million valuation. She is also the managing partner of Monarch Collective, the first investment platform exclusively dedicated to women’s sports. Monarch is now investing a $250 million fund with a stake in three NWSL teams and a European football club. In March, Monarch acquired a minority stake in Cleveland’s WNBA expansion team, becoming the first private equity firm to invest in the league.

In this episode of The Deal, Kara breaks down for Alex and Jason how Monarch became the first private equity firm approved to invest in the WNBA and why they chose Cleveland as their team. She also explains why she considers this moment the “third inning” of women’s sports investment and why she is willing to waste time with the right people. Kara also breaks down her belief that the key to derisking women’s sports is putting butts in seats.

You can also watch this interview on the Bloomberg Podcasts YouTube page.

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NBA fans, you’re about to see a whole lot more of Kenny Beecham. The founder of basketball media brand Enjoy Basketball first broke through in 2011 streaming NBA 2k games on Twitch. Since then, he has built a YouTube channel with over 700,000 followers, hosted altcasts on NBA TV and ESPN and interviewed Adam Silver. In October 2025, Kenny and Enjoy signed their biggest deal yet: a partnership with NBC Sports to produce original NBA programming, the network’s first partnership with a creator-led media company.

In this episode of The Deal, Kenny tells Jason and Alex why his appeal is based in the fact that he is “just a guy from Chicago.” He also shares how a cold email and getting stranded in a blizzard helped him close the deal with NBC. Kenny also explains how the YouTube “Adpocalypse” helped him build a basketball media juggernaut, how Allen Iverson changed the culture of basketball and why a show about NBA wives and girlfriends is such a hit.

You can also watch this interview on the Bloomberg Podcasts YouTube page.

See omnystudio.com/listener for privacy information.

Elle Duncan has heard your criticism of Netflix’s MLB Opening Day Coverage. And as the streamer’s first sports anchor, she has something to say about it.

In this episode of The Deal, Elle explains to Alex and Jason that there is a difference between constructive criticism and saying something is “too Netflix” and there’s a balance between "eventizing" sports and covering them. She also shares why she left ESPN after a decade and what it’s like to be on a desk with the notoriously anti-media Barry Bonds. Then, Elle talks about her other new role hosting USA Network’s 2026 WNBA coverage and why the growth of women’s sports depends on investing in coverage and giving ourselves permission to admit that some players are just better than others

You can also watch this interview on the Bloomberg Podcasts YouTube page.

See omnystudio.com/listener for privacy information.