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The topic for reader of the discussion is the phenomenon of military leadership in comparative contexts of different eras. This is a leadership of unrest, revolutions, rebellions, civil wars. The discussion brings together researchers engaged in study of mass armed struggle, rebellion in the Civil War of 1918–1922, and those involved in popular uprisings, unrest, mass movements of earlier eras of the Russian history. The figure of leader, chief as extended from the bottom or recognized by participants of mass armed movements, in our view, is productive to speculate about the general and particular differences and continuity in popular movements, in the algorithms of formation of military leadership. This problem is the essence of questions proposed to discussants. V. Buldakov offered and made popular the concept of “red troubles”, which makes explicit the reference to the Time of Troubles. The Ukrainian research tradition matches successively a powerful Cossack tradition and leader of the period 1918–1922, especially in the case of the Makhnovist movement. The situation may be considered paradoxical. In the mass consciousness of three generations there are three (or four – the question is discussable) peasant wars of XVII–XVIII centuries. In relation to events of 1917–1922 it was about a peasant rebellion or the peasant war in 1917, and then there were the uprising in the rear non-Bolshevik regimes, kulak uprisings and political banditry in the Soviet territories. The Grand peasant war 1917–1922 was not noticed as peasant. This peasant war was not a peasant or, at least, a purely peasant. And the circle of leaders, and demands, and mythology of the rebels went back to Polish gentry or Cossack ideal. But in 1917, after semi-generational experience of 1905–1907, the mass of peasantry has demonstrated the ability to militarypolitical subjectivity.