This essay examines how Italian American socialists and anarchists perceived American institutions and political environment between the late nineteenth century and the mid twenties. It argues that a few radicals initially thought that American republicanism and liberties offered a fitting context for the establishment of a socialist society in the United States. It also points out that, after they moved to the other side of the Atlantic and experienced actual life under capitalism and the lack of trans-ethnic class solidarity among workers in their adoptive country, their earlier fascination with America and their great expectations died away, disillusionment set in, and the eventual disappointment even made some radicals receptive to nationalistic feelings.