The EU is a formidable power in trade. Structurally, the sheer size of its market and its more than forty-year experience of negotiating international trade agreements have made it the most powerful trading bloc in the world. Much more problematically, the EU is also becoming a power through trade. Increasingly, it uses market access as a bargaining chip to obtain changes in the domestic arena of its trading partners, from labour standards to development policies, and in the international arena, from global governance to foreign policy. Is the EU up to its ambitions? This article examines the underpinnings of the EU’s power through trade across issue-areas and across settings (bilateral, inter-regional, global). It then analyses the major dilemmas associated with the exercise of trade power and argues that strategies of accommodation will need to be refined in each of these realms if the EU is to successfully transform its structural power into effective, and therefore legitimate, influence.