Writing in Nationalist revolutionaries in Ireland, 1858–1928, Tom Garvin observed that ‘well over 40 per cent, perhaps 50 per cent, had lived outside Ireland for considerable periods … foreign experience was very important in the development of the leaders’. The impact of ‘foreign experience’ on leading nationalist revolutionaries, this article submits, pace Garvin, could have proved influential in the development of the Irish Revolution more widely. Between June 1919 and December 1920, Éamon de Valera toured the United States. From New York City to Salt Lake City, Alabama to Montana, the self-proclaimed president of the Irish republic addressed ‘Ireland’ in hundreds of interviews and speeches. Of these myriad public statements, his Cuban missive, notably, crossed national boundaries. Comparing Ireland's geo-strategic relationship with Great Britain to that of Cuba and the United States, de Valera's argument for an independent Irish republic was made in the Americas. How did de Valera's movement across the U.S. alter his political views of Ireland? How were presentations of de Valera's ‘Cuban policy’ mediated across the ‘Irish world’? How did discourse on the Monroe Doctrine inform Anglo-Irish negotiations between Truce and Treaty? Exploring de Valera's ‘Cuban policy’ as global case study, this article concludes, ultimately, can shift the historiographical significance of ‘foreign experience’ from nationalist revolutionaries in Ireland to the flows and circulation of transnational revolution.