The Deal with Alex Rodriguez and Jason Kelly Bloomberg

Mark Shapiro has a habit of making the unlikely happen. From marrying Ultimate Fighting Championship with World Wrestling Entertainment to making the call to hire Stephen A. Smith at ESPN, Shapiro finds a way to get deals done. Now, as president and COO of Endeavor and TKO—the publicly traded combination of WWE and UFC—he and Ari Emanuel are reshaping sports, media and entertainment. On the latest episode of The Deal with Alex Rodriguez and Jason Kelly, Shapiro reveals their guiding principle: Even in the most turbulent of media worlds, people love to watch games.

Shapiro made his name as the brash young head of programming at ESPN, greenlighting some of its most iconic programs, including Pardon the Interruption, the long-running talk and debate show hosted by Tony Kornheiser and Michael Wilbon. It was also Shapiro who overruled his direct reports by bringing in Stephen A. Smith for an audition, a decision that catapulted Smith to the very top of the sports media pyramid and redefined the medium around hot takes. (Smith is a guest on an upcoming episode of The Deal).

The pair work together still, with Smith now represented by Endeavor’s talent arm. Shapiro and his partner Emanuel (made famous by the fictional Ari Gold on Entourage) have built Endeavor into a multifaceted entertainment company heavily invested in sports. Its biggest deal was creating TKO, which went public last fall and now has a market capitalization of $16 billion.

Amid all the dealmaking, Shapiro—who in between ESPN and Endeavor ran Six Flags—says he’s focused on creating situations where talent inside his shop and out can keep moving forward.

You can also watch The Deal on Bloomberg Originals, YouTube or Bloomberg TV.
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Future Hall of Fame wide receiver Larry Fitzgerald said he always expected to be coached. Just not by a Wall Street banker. So when Frank Bisignano—then a senior JPMorgan Chase & Co. executive and now CEO of Fiserv—pushed a twentysomething Fitzgerald to think about life beyond the National Football League, it changed his trajectory.

That led to a series of internships between football seasons, touching on everything from venture capital to real estate and mezzanine financing. Fitzgerald played football for more than a decade after his run-in with Bisignano, spending his entire pro career with the Arizona Cardinals. But thanks in part to that first internship (at JPMorgan), he’s since invested in more than 160 companies, ranging from tech firms to an Indian cricket team. One of his breakthrough business moments came in 2020, when he joined the board of Dick’s Sporting Goods Inc., a publicly traded retailer that now has a market capitalization of about $16 billion.

Arguably among Fitzgerald’s most interesting deals is one tied to his oldest passion: chess. He started playing as a kid, an effort by his parents to focus a restless young mind. His public affinity for the game led to a meeting with Danny Rensch, the “chief chess officer” of Chess.com. Fitzgerald invested in the company and played in a celebrity tournament. He even allowed Chess.com to create a bot trained on his previous matches.

You can also watch The Deal on Bloomberg Originals, YouTube or Bloomberg TV.
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Twenty-five years later than expected and following several false starts, women’s professional soccer looks to finally be planting long-term roots. And at the center of it all is one of the icons of a US championship team.

Brandi Chastain, whose electrifying penalty kick in front of more than 90,000 screaming fans at the Rose Bowl sealed the 1999 Women’s World Cup, is a co-owner of Bay FC, the latest franchise to join the fast-growing National Women’s Soccer League (NWSL). So what’s the difference with this league, this time, after two earlier failures? Solid investment for the long haul. 

The moment seems to have arrived for women’s soccer, as it has for the broader profile of women in American sports. Bay FC was taking the field this spring just as the women’s edition of NCAA March Madness kept breaking its own records, driven by outsized performances and personalities like Caitlin Clark and Angel Reese. This new era of attention and support for women’s sports hasn’t seen its equal since Chastain’s famous, jersey-shedding celebration of her World Cup victory. That team—and its successors—produced stars that broke through into the broader public consciousness: Carli Lloyd, Alex Morgan and Megan Rapinoe among them.

But all that excitement needed money to sustain it. These days, Chastain has linked up with Sixth Street Partners, a global investment firm that’s developed a business case for women’s sports. 

Now, Chastain says, it’s up to her and her fellow owners to leverage not just the money, but the expertise. That means blending her experience as a World Cup winner, Olympic gold medalist and coach with the analytics generated across reams of Sixth Street spreadsheets to produce a winning team.
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From George Steinbrenner to Jerry Jones, Gerry Cardinale has done deals with some of the biggest names in sports.

These days, the Goldman Sachs alum is making moves under the auspices of RedBird Capital, the firm he created in 2014. His purchase of the AC Milan soccer franchise and the resurrection of American football’s XFL stem from two decades spent at the intersection of sports, finance and media.

At Goldman, Cardinale got a chance to give advice to none other than Steinbrenner, aka “The Boss,” most notably about the 2002 launch of the YES Network. That debut brought its own made-for-TV drama, pitting Steinbrenner against New York Knicks and New York Rangers owner James Dolan (who also controls Madison Square Garden). Cardinale was in the middle of that fight as a key adviser to Steinbrenner—and his work took him deep into the Yankees front office.

Cardinale and Rodriguez recall a Manhattan dinner they shared with Yankees President Randy Levine where they mapped out the roster that would ultimately deliver the 2009 World Series championship to the Bronx. Around the same time, Cardinale and Goldman teamed up with the Yankees and the Dallas Cowboys to create the hospitality company Legends, born in part out of Cardinale’s desire to link the ambition of Steinbrenner to the only other owner who could match him: Jerry Jones.

Leaving the lucrative confines of his Goldman partnership also opened up more opportunity for Cardinale to be an investor. He teamed with Dwayne “The Rock” Johnson and Dany Garcia to restart the XFL, and the trio subsequently engineered its merger with the USFL, the other big springtime pro-football league, to create the UFL. The new-look league played its first game earlier this week. Cardinale then went a step further in soccer, buying AC Milan, one of the best-known clubs in the world.

You can also watch The Deal on Bloomberg Originals, YouTube or Bloomberg TV.
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Hannah Storm’s analysis of how pro basketball got so big is pretty simple: That guy from North Carolina.

“What happened was Michael Jordan,” Storm said on the latest episode of The Deal with Alex Rodriguez and Jason Kelly. She should know, since the pioneering television broadcaster and ESPN anchor was there from before the beginning. She had a front-row seat—literally—to basketball’s popular explosion in the 1980s, when Jordan electrified not just the sport but the broader culture. Storm witnessed how basketball came to compete with and eventually usurp baseball in the national conversation. 

One of Storm’s key assets when it came to explaining basketball and other sports to viewers was her familiarity with the inner workings of the industry. Her father, the late Mike Storen, was the commissioner of the American Basketball Association (which ultimately merged with the National Basketball Association), as well as the first general manager of the Indiana Pacers. (In case you’re wondering, Hannah Storen became “Hannah Storm” thanks to a stint as a hard-rock deejay in the 1980s).

These days, basketball feels like it’s at another catalytic moment, as one generation (LeBron James, Stephen Curry, Kevin Durant) edges toward the end of long careers and make way for a new wave. That younger cohort includes players like Nikola Jokic and reigning most-valuable-player Joel Embiid.

As a sports broadcaster, Storm said her profession faces a challenge in covering the NBA. She explained that her colleagues must redouble their efforts to search out less obvious stories and characters rather than falling back on marquee names and teams.

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