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Fortune
Fortune
Business
Joshua Hong

Lakers, Clippers, Man City: why do so many sports owners have money on both sides of a situation?

LeBron James #23 of the Los Angeles Lakers and Kawhi Leonard #2 of the LA Clippers looks on during the game. (Credit: Photo by Adam Pantozzi/NBAE via Getty Images)

It takes a fortune far bigger than any sports team to buy one—and that fortune rarely sits still. It’s invested in startups, private holding companies and insurers. This year, three of the richest owners in sports have come under scrutiny for deals in which they had money on both sides.

Steve Ballmer had invested in Aspiration, the financial services company that signed his star player, Kawhi Leonard, to an endorsement deal. Manchester City’s owner, through his investment vehicle, covered some of the fees the club’s sponsors were supposed to pay, an independent commission found. And insurers controlled by former Los Angeles Lakers owner Mark Walter lent billions to companies tied to his financial empire, leading to lawsuits and an SEC investigation.

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