The question of just what kind of entity the European Union is or aspires to be has been a point of debate since the inception of the European project in the 1950s. Whilst descriptive metaphors abound, perhaps the most evocative and prevalent are those depicting the EU either as a neomedieval or Westphalian entity. Although it is easy to see these metaphors as directly opposed, this chapter starts from the premise that they point to a paradox at the heart of EU debates, with both capturing a part of current developments.