Below, I first point out that we tend to use democracy as a vague general concept that includes various types of constitutional arrangements. I suggest that it would be beneficial to differentiate between these more carefully. I discuss some points made earlier, especially by Michael Oakeshott and Bernard Crick. Due to their long careers, their work reflects long-term change in conceptions of democracy. The huge corporate power and superpower mentality are discussed together with the question of the possibility for real representative, parliamentary systems in the contemporary world. I additionally lean especially on Sheldon S. Wolin’s work. I emphasize that the early critique of behaviourism connects the three theorists profoundly. They also share a historico-philosophical style of writing without the fear of commenting on contemporary developments. I also examine some of today’s surveillance and manipulation techniques posing a threat to ‘democracy’. With help from the crucial case of Julian Assange, and his illegal imprisonment, I ask if late-modern ‘democracies’ already have crossed such boundaries that even the minimal criteria of democracy are fading. I try to bring some coherence to the named topic of the conceptual and practical mess around democracy and suggest some possible approaches for future studies.