As Prohibition took hold Sam and Rose began to give gifts of wine that they were able to smuggle to their customers. As their customers became more interested in the liquor they gradually became more serious bootleggers. Maceo allied himself with local gang leader and power broker Ollie Quinn and opened a speakeasy.McComb (1986), p. 161</ref> Eventually Quinn became Sam's mentor and associate. He and the brothers opened the Hollywood Dinner Club, the Gulf coast's most elegant night club at the time. Sam's smooth personality quickly made him the "face" of the nightclub.