The European question has divided the Labour Party and the progressive left for over 50 years. The contemporary left-wing antithesis to the EU harks back to Bennite anti-marketeer narratives: a neoliberal EU undermines the potential for national progressive policies in relation to labour markets, state intervention and finance. However, many make the case that the EU’s four freedoms support a progressive politics: the single market project embeds social and workers’ rights, challenges member state support for large corporate interests and facilitates free movement for EU citizens. There is, in short, a progressive dilemma for the British left in relation to the European issue, which the authors navigate through the analysis of four policy issues that arose during the Brexit debate and remain significant for British politics and for the left in particular: free trade and the single market, industrial policy and state aid, free movement of persons and finance.