In 2023, David Rubenstein, a cofounder of the private equity giant Carlyle Group with an estimated net worth of $4.3 billion, was negotiating to buy the Baltimore Orioles when a Zoom call turned insulting.
Lawyers and investment bankers representing the buyers and the team’s owners were discussing the deal. Someone questioned whether Rubenstein, now 77, and his prospective partner, investment executive Mike Arougheti, 53, understood debt — though they’d spent their careers in finance.
“I announced to everyone that I had heard enough, I was dropping out of the deal and getting off the Zoom, and disconnected,” Rubenstein writes in “Inside the Owner’s Box: Conversations on Power and Leadership in Sports” (Simon & Schuster), out September 22. “That occurred in the space of about ten seconds.”
The blowup nearly ended his pursuit of his hometown team. “I began to think that maybe I had no business buying the team in the first place,” he writes. About two weeks later, he revived negotiations, eventually completing a $1.7 billion purchase in 2024.
Buying the team gave Rubenstein plenty of opportunities to have his judgment questioned again. His book, which includes interviews with fourteen other owners, reveals what comes with owning a major professional sports franchise: fans heckling you in the grocery store, trades you’re still defending years later and colleagues telling you just how stupid your latest decision was.
Brooklyn Nets owner Joe Tsai, 62, knows how quickly an expensive trade can turn an owner into a target. The Alibaba cofounder, worth an estimated $12.1 billion, still takes heat from fans for the January 2021 trade that brought James Harden to Brooklyn alongside Kevin Durant and Kyrie Irving.
Durant and Irving had arrived in 2019, before Tsai became controlling owner. Harden was his gamble, acquired at the cost of players and valuable draft assets. The trio never delivered a championship.
“The Harden decision was definitely on my watch,” Tsai tells Rubenstein. “That’s why I’m hated by fans on social media.”
Even before taking control, Tsai faced a decision that tested his personal loyalties. General manager Sean Marks called in 2018 to explain that the Nets were trading Jeremy Lin.
“Sean, if you trade Jeremy Lin, I will be hated in China, Taiwan, and Hong Kong,” Tsai recalls telling him. “The entire Chinese community will hate me forever.”
Marks replied, “That’s why I’m calling you.”
Tsai accepted the rationale. But he wanted a way to explain himself to fans, so he opened a Twitter account despite objections from his communications team. He promised to discuss sports rather than Alibaba or politics.
“I need to have a direct channel to communicate with our fans,” he tells Rubenstein. “I can’t have the New York Post interpret.”
Seattle Mariners owner John Stanton, 71, gets feedback without opening an app. An approximately eighty-year-old woman wearing Seahawks gear once planted herself in front of his grocery cart, announcing that she had important things to say.
Fortunately, she liked how the team was doing. When fans are unhappy, Stanton tells Rubenstein, “Sometimes you’re hearing yelling from another corner of the grocery store.”
Ted Leonsis, 69 and worth an estimated $4.5 billion, made his fortune selling his marketing company to AOL and then working as an executive there. He bought the Washington Capitals in 1999, well aware that success in one industry wouldn’t automatically transfer to sports.
Two years later, he helped push for the Capitals to acquire hockey superstar Jaromír Jágr.
“I advocated maybe a little more enthusiastically than I should have,” Leonsis tells Rubenstein. “We brought Jaromír here, and that was a disaster. I made a mistake.”
After two-and-a-half disappointing seasons, Washington traded Jágr to the Rangers in 2004, continuing to pay part of his salary.
Another intervention worked. Hockey executive Dick Patrick advocated locking up Alex Ovechkin with a thirteen-year contract, and Leonsis approved it. Then-NBA commissioner David Stern called with a blunt assessment.
“Thirteen years is the stupidest thing I’ve ever heard,” Leonsis recalls Stern saying. Years later, Leonsis’ regret was that he hadn’t offered 15.
Did Stern acknowledge being wrong? “No, but they changed the rules, so you can’t give deals like that anymore,” Leonsis tells Rubenstein.
The arithmetic makes satisfaction difficult. Atlanta Hawks owner Tony Ressler describes “the frustration of the fact that twenty-nine out of thirty teams fail every season.” Every owner’s championship plan requires almost everyone else’s to fail.
Rubenstein also discovered that ownership couldn’t recover everything he’d lost. Visiting his childhood row house for a team-produced film, he met the current owner, who had no idea who he was. She mentioned finding boxes of baseball cards in the basement and throwing them out.
For decades, he’d assumed that his mother had gotten rid of his collection long ago. “I did not have the heart to tell the current owner” that the cards were “probably worth much more than the house,” he writes.
Tsai’s basketball memories include skipping constitutional law classes at Yale to play pickup games. One opponent was future Supreme Court Justice Brett Kavanaugh, who he calls a “decent player.”
His current ambitions require better players. “We need to win a championship,” Tsai tells Rubenstein. “We need to prove ourselves.”
Still, ownership supplies a pleasure that running Alibaba cannot.
“I can be chairman of a public company, but there are thousands of public companies. There are only thirty NBA owners,” Tsai says. “When you have something that other people don’t have, it feels pretty good.”
