The 500 Club was a front for an illegal gambling operation. To draw gamblers, he had such big name entertainers as Frank Sinatra, Sammy Davis,Jr., Dean Martin and Jerry Lewis perform at the club. Back in the 1940s, 50s and 60s. D'Amato's supper club and gambling den on South Missouri Avenue, where the doors opened at 5 p.m. and closed at 10 a.m., was the world’s most notorious fairground. The biggest names in politics, sports — and the mob — mingled, smoked, drank, gambled (long before it was legal) and cut deals in secret rooms filled with roulette wheels, craps tables, baccarat and high-stakes card games, all protected by a police department on Skinny’s unofficial payroll.