In the 1950s, Colacurcio entered the jukebox, cigarette, and vending machine businesses. Business rivals claimed that he used threats to control the trade. With money earned from these businesses, Colacurcio started investing in bars, restaurants, and clubs. To avoid trouble obtaining liquor licenses, Colacurcio had relatives and associates front as the business owners. In 1957, he was subpoenaed to testify before the U.S. Senate Rackets Committee. Although Colacurcio never testified, Committee Counsel Robert F. Kennedy did question him about his alleged racketeering activities in Seattle.