September 4, 2026
Jeffrey Eilender recently spoke to Business Insider about the legal implications of Spotify executive and sports media personality Bill Simmons’ admission that he used a proxy to place NFL futures bets on his behalf.
In the article, “So, how bad is Bill Simmons' proxy betting mishap? We asked legal experts what could happen,” Business Insider examines the potential consequences Simmons could face after admitting that his daughter’s boyfriend, a Massachusetts resident, placed bets for him while Simmons was in California, where online sports betting is illegal. The arrangement also appears to have violated Massachusetts gaming laws, which prohibit proxy betting although sports betting is legal in the state.
Though Simmons claims that he did not know of the proxy betting laws, Jeff explains that Simmons’ lack of knowledge about the applicable rules is unlikely to serve as a complete defense. “The law presumes that people know the law — even if they do not,” he tells Business Insider.
The article also explores the potential consequences Simmons could face from FanDuel and Massachusetts regulators. Although Simmons is unlikely to face significant penalties, the Massachusetts Gaming Commission confirmed that it is reviewing the matter.
Read the full article in Business Insider (Subscription may be required).
Jeffrey M. Eilender is the co-managing partner of Schlam Stone & Dolan LLP and co-chair of the civil litigation group. He regularly contributes to the firm’s New York Commercial Division Blog and has been recognized on the New York Metro Super Lawyers® list in Business Litigation, Civil Litigation, and General Litigation since 2010.