Teresa Carreño’s 1887 operatic season in Caracas is a notorious episode in Venezuelan musical history: an attempt to launch an Italian opera company by the country’s most celebrated pianist that ended in dismal failure. Invited by President Guzman in 1885 to give a series of recitals – and subsequently to start a permanent opera company – Carreño was by then in the glory years of her career. Studies of Carreño have long emphasised the symbolic importance of Carreño’s time in Caracas in the 1880s, highlighted by her composition of an 'Himno a Bolivar' during the visit. Less frequently discussed, however, is that the majority of the operatic troupe were in fact recruited from New York, where Carreño had settled in the previous decade, and from where she had pursued concert tours across the United States. The chapter reassesses Carreño’s failed operatic experiment both through the lens of her North American networks and against the shifting relations between New York, Venezuela and Italy at this time. It provides a framework for later activities within Latin America by the US operatic gramophone industry, and underlines the problematic status of Italian opera’s 'civilising' ambitions for local Venezuelan elites. If Venezuela could easily be subsumed into clichés of italianità abroad, then Italian opera was an uneasy and surprisingly mobile symbol of cultural progress.