The Deal with Alex Rodriguez and Jason Kelly

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).

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Serena Williams revolutionized tennis—that much is unquestioned. With her sister and fellow superstar Venus beside her and father Richard behind them both, Williams went on to transform the way the world looks at tennis stars. Having now put her racket down, she has moved on to the world of finance and started her own venture capital firm, Serena Ventures. But this time, she’s doing it all on her own. On the latest episode of The Deal with Alex Rodriguez and Jason Kelly, Williams explains just how these early financial lessons formed the basis of success in her second act.

In tennis, Williams is widely regarded as the greatest of all time. In business, she exudes similar ambition for her growing business empire. Williams says she’s built a team that she trusts while staying intimately involved with every major decision. Diving into the details is something she’s known for—Williams was literally at the table for her first big shoe endorsement deal, with Puma.

Serena Ventures has invested in more than 20 companies in its first fund, and that’s in addition to the dozens of angel investments Williams has made. She’s also focused much of the firm’s energy on investing in companies run by traditionally underrepresented founders, especially women and people of color. (Only 2% of venture capital goes to companies led solely by women, while just 1% goes to firms with Black founders.)

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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.

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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.

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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.

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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.

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George Steinbrenner’s decision back in 2004 to pair Derek Jeter and Alex Rodriguez—two generationally talented baseball players—turned out to be one of the biggest and arguably most successful deals in New York Yankees history. Or all of sports history for that matter.

The results that sprang from the Boss’s machinations became clear: a perennially contending team, a 2009 World Series championship and yes—a lot of headlines. For Jeter, all of that on-field success—and his ability to manage it so gracefully—made him one of the most sought-after athletes both during and after his baseball career. On the latest episode of The Deal with Alex Rodriguez and Jason Kelly, he tells the backstory of how Michael Jordan made him the first baseball player to be endorsed by a then-nascent Jordan Brand, and reveals some never-before-heard details of his tumultuous, three decade-long relationship with A-Rod.

Jeter distinguished himself during a 20-year career played entirely for the Yankees, winning five World Series rings during that time. The last of the titles (and the last time the Yankees won it all) was accomplished with Rodriguez just a few feet away at third base. The pair had known each other since they were teenagers and even shared a 1997 cover of Sports Illustrated.

Jeter was a first-ballot Hall of Famer, inducted into Cooperstown in 2020 with 99.7 percent of the vote. Shortly after retiring, he joined the ownership group of the Miami Marlins and served as the team’s chief executive (the first Black man to hold such a position in Major League Baseball), overseeing both the business and operations of the club. He resigned in 2022, citing strategic differences with his fellow Marlins owners.

Of late, Jeter has been splitting his time between his young family, investing, endorsements and broadcasting—reuniting with Rodriguez to provide on-air baseball commentary. 

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Back in the day, a professional athlete played, maybe made some money and then hung it up. When they retired, there was sometimes a chance to work for a local company to leverage whatever fame they had accrued. But a few players have realized there was much more to be done both before and after that final whistle blew. They also recognized it would be a good idea to get some help. That’s where Constance Schwartz-Morini comes in.

On the latest episode of The Deal with Alex Rodriguez and Jason Kelly, we speak with this National Football League executive-turned-manager who’s worked with everyone from Snoop Dogg to Erin Andrews.

Schwartz-Morini explains how she’s created one of the most successful playbooks for second acts—two high-profile examples of which are former football stars Deion Sanders and Michael Strahan. She says that Strahan embodies what she’s trying to do with athletes and entertainers: help them transcend sports into the broader culture.

One of her most prominent current projects is happening not in New York (her hometown) or Los Angeles (her current home), but in the Rockies. Schwartz-Morini is a primary architect of the post-NFL phenomenon that is Sanders, aka Coach Prime. A man who pushed himself into the zeitgeist as “Prime Time” back when he played for both the Atlanta Braves and Atlanta Falcons, Schwartz-Morini managed to guide Sanders toward coaching, first at Jackson State and then now at the University of Colorado Boulder.

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Was Michael Strahan always going to be a ubiquitous presence—from Good Morning America host to NFL commentator to having his own line of clothing at Men’s Wearhouse? Maybe—but if you ask him, he would tell you it wouldn’t have happened were it not for his move from Texas to New York. There was also another thing: winning a Super Bowl.

On this episode of The Deal, the ex-football Giant says trial by fire in the most unforgiving of sports towns set him on the path to success in everything else.

Strahan has put together a post-NFL career that’s unique for its simultaneous proximity and distance from the game. On one hand, there he is every Sunday during the season, jawing with a coterie of ex-players and coaches on Fox NFL Sunday. But during the week, he’s a co-host of Good Morning America, alongside Robin Roberts and George Stephanopoulos. Then there are the apparel lines with JCPenney and Men’s Wearhouse, and an annual collaboration with Starter for the Super Bowl.

His co-architect in all of this is Constance Schwartz-Morini, a former NFL executive-turned-manager who’s also worked with Snoop Dogg, Erin Andrews and Deion Sanders. Much of that work has come under the auspices of SMAC Entertainment, the firm Strahan and Schwartz-Morini created in 2011. We also got a chance to sit down with Schwartz-Morini, who is our guest on episode three of The Deal, dropping March 15.

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Maria Sharapova, the global tennis icon who spent her career defeating the sport’s best, is looking for some losers. On the premiere episode of The Deal with Alex Rodriguez and Jason Kelly, she tells us exactly what she means.

For many, Sharapova is a figure frozen in time. It was 2004 when she stunned Serena Williams on Centre Court to win her first Wimbledon and first Grand Slam. Sharapova would go on to become (like Williams) one of the most recognized tennis players of her generation. These days, however, she’s turned her laser focus to dealmaking. 

Even as she was climbing to the top of the tennis world, the Russian-born star was already building a business resume—these days she’s reportedly worth in excess of $200 million. 

Now with her tennis career behind her, all of those off-court projects have become a full-time job. With an attitude forged in the highest-pressure sporting arenas, she approaches a range of partnerships with a sly worldliness. One thing she’s keen to find? People who have seen it all go sideways. Sharapova says that only those who have lost can eventually win.

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The Deal, hosted by Alex Rodriguez and Jason Kelly, features intimate conversations with business titans, sports champions and game-changing entrepreneurs who reveal their investment philosophies, pivotal career moves and the ones that got away. From Bloomberg Podcasts and Bloomberg Originals, The Deal launches on February 29, 2024. The Deal is available on Apple Podcasts, Spotify, iHeart, Bloomberg Carplay, or wherever you get your podcasts. You can also watch The Deal on Bloomberg Television, and Bloomberg Originals on YouTube.

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