So, how bad is Bill Simmons' proxy betting mishap? We asked legal experts what could happen.

Business Insider | 02-09-2026 09:52pm |

Bill Simmons, a Spotify executive and podcaster, revealed on his show that he had someone else place sports bets for him because he lives in California where online sports betting is illegal, while the other person is in Massachusetts where it is legal. Legal experts note that proxy betting is prohibited by sportsbooks and state law, but any punishment for Simmons is likely to be minor.

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