This paper aims to raise important questions about the recent political evolution of the Sinn Féin party (SF) in Ireland. It examines the evidence for and against the propositions that SF is best viewed as a nationalist populist or a socialist party, and looks as whether or not a nationalist populist formation can ever be viewed as a party of the radical left. This investigation involves a critical examination of SF’s political strategy in both parts of Ireland since the signing of the Good Friday Peace Agreement in 1998, as well as the record of its participation in Northern Ireland governments that have pursued policies of neo-liberal privatisation, and its participation in campaigns against the Lisbon and Nice Treaties. But the paper also, and centrally, examines SF’s relationship with the Confederal Group of the United European Left/Nordic Green Left (GUE/NGL), to which its MEPs have belonged since it first entered the European Parliament. In examining what lies behind the decision to align with the GUE/NGL, the paper considers whether Group membership has had any impact on SF’s policies at home or in Europe. It also raises questions about what the party’s membership of GUE/NGL tells us about the nature of that EP Group itself, and about the ideological reconfiguration of the European radical left in recent years.