Why Hollywood Won't Cast Tobey Maguire Anymore
Abigail Rogers
Updated on March 08, 2026
Maguire's penchant for gambling is the stuff of Hollywood legend. In 2011, his name was linked to an illegal poker club that allegedly involved Matt Damon, Ben Affleck, and DiCaprio. Maguire was subsequently sued for his involvement after it was uncovered that the ringleader, Bradley Ruderman, had been using his investor's money in their poker games. Maguire settled in 2012 to avoid litigation, according to Celebuzz. Two years after Maguire's settlement, a woman named Molly Bloom, who organized many of the high-profile poker games, wrote a scathing memoir called Molly's Game, which detailed some of Maguire's alleged bad behavior. "[Maguire] was the worst tipper, the best player, and the absolute worst loser," Bloom wrote (via Vanity Fair). During one particular game, Bloom claims that Maguire made her "bark like a seal who wants a fish" to obtain a $1,000 chip. After Blown laughed nervously, Maguire allegedly fired back, saying, "I'm not kidding. What's wrong? You're too rich now? You won't bark for a thousand dollars?" That doesn't sound very Spidey-like.