The Deal with Alex Rodriguez and Jason Kelly – Details, episodes & analysis

In this episode of The Deal, Alex Rodriguez and Jason Kelly talk with David Rubenstein, co-founder of The Carlyle Group, about his recent purchase of the Baltimore Orioles. Rubenstein tells the hosts about 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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In this episode of The Deal, Alex Rodriguez and Jason Kelly sit with tennis champions Billie Jean King and Ilana Kloss to discuss the current buzz around women’s sports. King and Kloss, the dreamer and builder (respectively) behind Billie Jean King Enterprises, King says, tell the hosts about their investments in the Los Angeles Dodgers and Angel City FC, the story behind how they helped launch the Professional Women's Hockey League and the lessons they think athletes should learn about the business of sports. 

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On this episode of The Deal, Alex Rodriguez shares his excitement for attending the Olympics as a fan, reminisces about historic moments of the Games and analyzes their impact on athletes’ careers and brands. The conversation then shifts to Masai Ujiri, founder of Giants of Africa and president of the Toronto Raptors. Ujiri tells Jason Kelly about his journey from scouting talent in Africa to leading social and economic development on the continent through basketball.

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In this episode of The Deal, Jason Kelly and Alex Rodriguez reflect on baseball legend Cal Ripken Jr. and his influence on Rodriguez and the broader baseball community. Then Ripken tells Kelly about his business partnership with Josh Harris and David Blitzer, and their effort to expand youth sports. He also discusses the effect his father had on his career and the challenges of building a business that remains true to the Ripken family’s core values.

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In this episode of The Deal, Monarch Collective's Jasmine Robinson tells Alex Rodriguez and Jason Kelly about the business case for investing in women's sports leagues. Jasmine explains how her $150 million fund decided to invest in the NWSL and how she sees future growth opportunities for women's sports.

(Corrects to remove reference to the WNBA in first paragraph.)

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In this episode of The Deal, The Chernin Group's Jesse Jacobs tells Alex Rodriguez and Jason Kelly about a few of his notable deals, including Barstool Sports, the Professional Lacrosse League and his recent venture in Unrivaled Sports alongside Josh Harris and David Blitzer. Jesse shares his unique approach to business, the impact of digital media on sports and his thoughts on the evolving landscape of college and youth sports markets.

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In this episode of The Deal, entrepreneur Joe Pompliano tells hosts Alex Rodriguez and Jason Kelly about his rise in the sports media landscape, potential directions for sports valuations and future trends in sports media.

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In this episode of The Deal, Jessica Gelman, chief executive of Kraft Analytics Group, tells Alex Rodriguez and Jason Kelly how she navigates the intersection of business and sports with a special focus on the transformative impact of data analytics. Alex and Jason also discuss Willie Mays' legacy and the lessons they learned from Reggie Jackson at a celebration of the Negro League.

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With all the money pouring into sports these days, big-time investor Marc Lore says he has an additional metric for success: happiness. On the latest episode of The Deal with Alex Rodriguez and Jason Kelly, Lore lays out his thinking on some of his deals, including a few with Rodriguez. 

Lore and Rodriguez initially tried to buy the New York Mets, a race they ultimately lost to billionaire hedge fund manager Steven Cohen. Then came the Minnesota Timberwolves and Lynx, and the pair jumped. There’s currently a lot of happiness in Minnesota about the Timberwolves’ performance, given their initial success in the NBA playoffs.

The 52-year-old Lore made his fortune as an entrepreneur through a series of startups, including Diapers.com and Jet.com, which he and his partners sold to Amazon and Walmart, respectively. Those experiences pushed him toward a near-obsession with company culture and mission. He’s created a framework he dubs VCP—which stands for “vision, capital and people.”

The capital in Lore’s equation has come quickly and seemingly easily. Diapers was sold to Amazon for more than $500 million and Jet.com was acquired by Walmart for about $3.3 billion. Yet, Lore insists the drive was about more than the cash, a lesson he learned with the Diapers deal.

“After the money was wired to our bank account, we sort of said, ‘We should be celebrating right now,’” Lore says. “And we’re like, depressed. And it just goes to show you, it wasn’t about the money. Like the mission that we had set out was kind of crushed with the sale to Amazon.”

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Stephen A. Smith says he’s always been ambitious, but nothing fueled a burning drive to succeed like being fired from ESPN. His exit from the sports network in 2009 radically changed how he felt about himself, Smith says—and how he wanted to make a living.

After ESPN and Smith parted ways, he began the long road back, starting on radio and leveraging his experience as a print journalist to develop sharp points of view. He eventually built a following whose size effectively made his return to TV inevitable. 

After resuming his position in front of the camera, Smith quickly helped remake the modern sports media landscape. Now 56, he’s widely credited (or derided) for the “hot take” version of sportscasting that now dominates ESPN, Fox Sports and social media. It’s literally in the name of his flagship ESPN morning show, “First Take,” which he initially popularized with Skip Bayless. It now features Smith with a rotating cast of sparring partners, as well as moderator Molly Qerim. 

Yet Smith has constantly stretched himself beyond ESPN—and sports—most notably through his podcast, The Stephen A. Smith Show, which he created and runs through his own production company. With more than 600,000 subscribers to its YouTube feed alone, Smith says he’s more convinced of his ability to flex that popularity for another record contract with ESPN (his current deal is up next year).

You can also watch The Deal on Bloomberg Originals, YouTube or Bloomberg TV.

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