This article discusses the European Union (EU)'s strategic adaptation to the relative decline of the United States (US)-led Western world order by introducing the concept of hedging: a strategy of concomitant engagement with the system leader and its competitors aiming to minimise the risks of confrontation with either of them. To grasp the EU's shift towards strategic hedging, the article analyses the subsequent 2003 Security Strategy, 2008 Implementation Report, 2015 Strategic Review and ongoing 2016 Global Strategy, and then puts the latter's core concepts of ‘principled pragmatism' and ‘strategic autonomy' into perspective vis-à-vis international developments since 2016, related to ‘America First' and the Sino-American rivalry. The article ultimately argues that, confronted with global power diffusion but constrained by the preponderance of transatlanticism, hedging has become a primary strategic option for the EU to emancipate from the US without alienating it and to compensate for the waning of the Western world order.