When Edwin Sutherland introduced the concept of white-collar crime, he referred to the respectable businessmen of his day who had, in the course of their occupations, violated the law whenever it was advantageous to do so. Yet since the founding of the American Republic, numerous otherwise respectable individuals had been involved in white-collar criminality. Using organized smuggling as an exemplar, this narrative history of American smuggling establishes that white-collar crime has always been an integral part of American history when conditions were favorable to violating the law. This dark side of the American Dream originally exposed itself in colonial times with elite merchants of communities such as Boston trafficking contraband into the colonies. It again came to the forefront during the Embargo of 1809 and continued through the War of 1812, the Civil War, nineteenth century filibustering, the Mexican Revolution and Prohibition. The author also shows that the years of illegal opium trade with China by American merchants served as precursor to the later smuggling of opium into the United States. The author confirms that each period of smuggling was a link in the continuing chain of white-collar crime in the 150 years prior to Sutherland’s assertion of corporate criminality.