In this episode of the Vienna Coffee House Conversations, Ivan Vejvoda welcomes Niccolò Milanese, a political thinker, activist, and co-founder of European Alternatives, a transnational civil society movement dedicated to democracy and equality beyond nation-states. Milanese brings his expertise on European political trends, democratic struggles, and the challenges posed by rising authoritarianism. Their conversation explores the fragility of democracy in Europe amid global turbulence, touching on the European Union’s role in upholding democratic values, the impact of the Russo-Ukrainian War, and the resurgence of great power politics. Milanese reflects on the continuity of struggles for freedom, linking Ukraine’s fight for sovereignty to past democratic revolutions. He critiques the failures of Western elites in conveying the existential stakes of these conflicts and examines how corporate and technological forces have eroded democratic engagement. The discussion also delves into populism’s rise across Europe, the socioeconomic factors fueling far-right movements, and the urgent need for a democratic response to authoritarian tendencies. Milanese highlights the importance of grassroots activism, drawing on recent movements in Serbia, Georgia, and other regions resisting democratic backsliding. The episode concludes with insights into transnational civil society’s role in shaping the future of European democracy and the EU’s strategic direction in an increasingly unstable world.