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Owning a professional sports team is not for the faint of heart. Results are volatile and wins and losses come with the strong emotions of a city’s fan base. But it’s a sound investment for the right type of business leader, and the value of professional teams has been steadily rising over the past several years. Two legendary owners with very different backgrounds meet for this conversation about what it’s like to have a major stake in the game. Alex Rodriguez wrapped up an incredible career in major league baseball in 2016, after playing for 22 years. He’s gone on to found the investment firm A-Rod Corp. and recently bought a stake in the NBA’s Minnesota Timberwolves and WNBA’s Lynx. David Rubenstein is a businessman, lawyer and co-founder of The Carlyle Group private equity firm. In 2024, he became the principal owner of the Baltimore Orioles, his hometown MLB team. Businessman Gregg Lemkau, co-CEO of the merchant bank BDT and MSD Partners, moderates the conversation.