Billionaires Detail the High-Stakes, Often Humiliating Reality of Owning Sports Teams

Owning a professional sports franchise comes with its own unique set of pressures and public scrutiny, as revealed by several billionaires in David Rubenstein's new book, "Inside the Owner’s Box: Conversations on Power and Leadership in Sports." The experience can range from facing criticism in the grocery store to making multimillion-dollar decisions that draw widespread backlash.

Rubenstein, co-founder of the Carlyle Group, recounted a moment during negotiations to buy the Baltimore Orioles when lawyers questioned his and his partner's understanding of debt, despite their extensive financial careers. This incident, which he detailed in his book, nearly derailed his $1.7 billion acquisition of the team in 2024. His book features interviews with fourteen other owners who have experienced similar, often humbling, situations.

Brooklyn Nets owner Joe Tsai, a co-founder of Alibaba, shared his experience with fan criticism following the January 2021 trade that brought James Harden to Brooklyn. "The Harden decision was definitely on my watch," Tsai told Rubenstein. "That’s why I’m hated by fans on social media." He also recalled a difficult decision regarding Jeremy Lin's trade in 2018, which he feared would alienate fans in China, Taiwan, and Hong Kong. To manage fan communication, Tsai established a Twitter account to speak directly with supporters, bypassing media interpretation.

Seattle Mariners owner John Stanton noted that feedback is not limited to social media, recounting an instance where a fan approached him in a grocery store to discuss team performance. "Sometimes you're hearing yelling from another corner of the grocery store," Stanton said.

Ted Leonsis, who owns the Washington Capitals, admitted to a misstep in advocating for the acquisition of hockey star Jaromír Jágr. "We brought Jaromír here, and that was a disaster. I made a mistake," Leonsis stated. He also reflected on approving a thirteen-year contract for Alex Ovechkin, a move that then-NBA commissioner David Stern deemed "the stupidest thing I've ever heard." Years later, Leonsis expressed regret for not offering an even longer contract, though league rule changes ultimately prevented such deals.

Atlanta Hawks owner Tony Ressler highlighted the inherent difficulty in achieving ultimate success, noting that "twenty-nine out of thirty teams fail every season." The competitive nature of professional sports means that for one team to win, many others must fall short.

Rubenstein also shared a personal anecdote about visiting his childhood home, only to learn from the current owner that his childhood baseball card collection, found in the basement, had been discarded. He decided not to reveal the potential value of the cards, which he suspected were worth more than the house itself.

Despite the challenges, the allure of sports ownership remains. Tsai noted the exclusivity of being an NBA owner, stating, "I can be chairman of a public company, but there are thousands of public companies. There are only thirty NBA owners." He added, "When you have something that other people don't have, it feels pretty good."