Psychoanalyst and Boxer Debate America's Gambling Addiction

In a conversation for CULTURED magazine, psychoanalyst Jamieson Webster and filmmaker/boxing gym founder Jay Bulger examine the psychology and societal impact of America's gambling boom. Bulger, who wrote about the Jontay Porter betting scandal for New York magazine, notes that 51% of men aged 18-35 gamble. He argues that legal betting apps like DraftKings and FanDuel have removed barriers to entry, making gambling as accessible as vaping. The discussion draws on Edmund Bergler's 1957 book The Psychology of Gambling, which posits that gamblers are unconscious masochists who seek loss. Bulger describes how gamblers he interviewed for his article felt a rush from losing, not winning. He criticizes the collusion between sports leagues, media, and betting platforms, predicting class-action lawsuits. Webster connects gambling to broader cultural trends of isolation and digital addiction. Bulger contrasts the abstract, synthetic nature of app-based betting with the physical reality of boxing, which he teaches at his Bronx Legends gym. The article also references David Bockino's book Over/Under, which traces sports betting's deep roots in American history, from 19th-century pedestrianism at Madison Square Garden to modern prediction markets like Polymarket and Kalshi. Legal sports betting in the U.S. reached $166.94 billion in wagers in 2025, with illegal betting estimated at $511 billion annually.