The article analyses two distinct approaches that Western leaders have taken to relations with Putin’s Russia. It argues that the dominant approach of fostering good relations with Vladimir Putin, prioritising these over support for longer-term democratic change in Russia, has not brought any results and is damaging the interests of Russian society, neighbouring countries and the West. The article analyses the prerequisites for deep change in Russia and argues that there is a need for the EU to comprehensively review and change its strategy towards Russia, putting democracy at its core. It discusses in detail the deterrence, containment and transformation elements of a new EU strategy. The article emphasises that the strategic approach of ‘democracy first’ in relations with Russia also relates to the future of democracy in general and should be a priority of EU–US cooperation.