Ryan Howard spent more than a decade as one of baseball’s most feared hitters. Since retiring, he’s built an interesting second act as an entrepreneur and investor, with bets spanning everything from the “Topgolf of baseball” to youth sports and professional soccer.

In this episode of The Deal, Ryan tells Alex Rodriguez and Jason Kelly how he transitioned from playing baseball to investing in ventures like Batter Up that will help more people play baseball, why making deals can feel like playing baseball, and which issues he thinks could shape the labor fight between the MLB and the players' union.

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

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Vanderbilt is having a moment. The university has transformed from a respected southern institution into one of the country’s most selective and sought after schools. Athletics has become an increasingly important part of that rise. At the center of it is Vanderbilt University’s Vice Chancellor for Athletics and University Affairs and Athletic Director.

In this episode of The Deal, Candice Storey Lee joins us to discuss what it takes to build a winning culture, and how athletic success can amplify a university’s broader ambitions. They also talk about the forces reshaping college athletics, from NIL and revenue sharing to conference realignment, and what those changes could mean for athletes, universities, and fans.

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

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Alex Rodriguez and Jason Kelly recently had the opportunity to sit down again with David Rubenstein, co-founder of The Carlyle Group, to chat about his new book, “Inside the Owner's Box: Conversations on Power and Leadership in Sports.” That conversation got us thinking back to an earlier episode of The Deal, recorded shortly after Rubenstein's purchase of the Baltimore Orioles. We revisit that conversation, with Rubenstein telling the hosts why he bought his hometown baseball team, how he assembled the ownership group, and what the Orioles mean for the city of Baltimore.

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With the trade deadline in the rearview mirror, the Major League Baseball season is officially entering its final innings. So in this episode of The Deal, Alex Rodriguez and Jason Kelly break down some of the latest headlines, including what is happening with the negotiations over a collective bargaining agreement between the league and the players, the trade that may have guaranteed the Los Angeles Dodgers another World Series win, and why Alex is still bullish on his New York Yankees. Plus, Alex previews a very special 50th anniversary celebration for the Seattle Mariners.

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Investors have poured money into youth sports in recent years, with some reports saying the industry is worth as much as $40 billion. It’s no surprise, then, that renowned investors David Blitzer and Josh Harris partnered with The Chernin Group in 2024 to start Unrivaled Sports, a growing portfolio of youth sports investments across baseball, softball, flag football, and more. Unrivaled’s chairman and CEO Andy Campion says they’re only just getting started.

In this episode of The Deal, Andy tells Alex Rodriguez and Jason Kelly why he left Nike to go all in on youth sports. From the sidelines of a youth baseball tournament at Cooperstown All-Star Village, he explains the business model making youth sports more accessible while also offering premier experiences.

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

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The 2026 World Cup is done and the numbers are astounding. FIFA reportedly expects to bring in $15 billion in revenue, blowing past their original projection of $12 billion. This number isn’t surprising considering that almost 7 million people attended the tournament’s 104 games and 60 million people in North America tuned into Sunday’s final.

In this episode of The Deal, we dig into the stories beyond these record-smashing numbers. First up, Jason talks to Fox Soccer broadcaster Melissa Ortiz about how this World Cup compared to the others she has covered as a broadcaster and played in as a member of the Colombian national team. She also explains what made the officiating so frustrating and why she is already looking forward to next summer’s women’s World Cup.

Next, Jason is joined by Bloomberg News sports reporter and Business of Sports co-host Vanessa Perdomo about what makes this World Cup such an incredible business story and why FIFA will likely be eager to host another major tournament in the U.S. She also gives her take on how the World Cup’s momentum will impact the MLS and predicts the future of hydration breaks.

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8AM Golf is a holding company whose portfolio includes 15 companies that touch nearly every aspect of golf. Started in 2018 by Howard Milstein, 8AM’s umbrella includes Golf Magazine, Miura Golf and a newly constructed course in Nashville built in partnership with Justin Timberlake. So, there is no one better to talk to about what is going on in the world of golf than the company’s CEO, Hoyt McGarity.

In this episode of The Deal, Hoyt dials in from St. Andrews to give Alex and Jason the inside scoop on running a holding company, including: what companies 8AM chooses to invest in, which ones they don’t and when they know it’s time to sell. Hoyt also shares his perspective on making golf more accessible to a new generation of golfers while also respecting the traditions of the old heads and what existential threats the sport is facing. Finally, Hoyt tells us why a golf course must be a “good hang” and about his personal trajectory from caddie to CEO.

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If you know nothing else about women’s hockey, you probably know Hilary Knight. The 5-time Olympic medalist has played the most games in U.S. Women’s Hockey history. She has also served as the captain of two PWHL teams and is one of the reasons the league exists in the first place. In 2019, Hilary was among several players who vowed to boycott any North American league that was not financially sustainable. In 2022, the players entered into a partnership with Mark Walter and Billie Jean King to launch the PWHL. Four years later, the league is selling out games at MSG and accepting a $100 million investment.

In this episode of The Deal, Hilary details for Jason and Alex the process of starting a league where players were partners from the jump and why Mark Walter and Billie Jean King were the right people to work with. She also explains how the momentum from this year’s Olympics bled into the PWHL season and why Heated Rivalry is one of the best things to ever happen to hockey. Finally, she shares her hopes for her post-playing career (spoiler alert! she wants to own a team) and the responsibility of being the face of her sport. Plus, Alex shares a business idea and tells Hilary why she reminds him of NBA Hall of Famer Grant Hill.

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