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The conclusion that the author draws after reading the proceedings of the General Assembly of the World Political Forum on the evolution of the international system 20 years after perestrojka is that, in times of great changes, it is difficult and dangerous to look for constants and continuity. If it still makes sense to speak about the legacy of perestrojka over two decades after the event, it is thanks to insights that have influenced our way of thinking more than others: in the first place, the courage and risk of innovation, the continuous pursuit of new scenarios and new perspectives that has to transcend the habits and the certainties of the past; secondly, the perception and force of new thinking, born from the ashes of the conflict between blocs and capable, at least potentially, of designing a new system of interaction and coexistence. Many hypotheses and intuitions have been left on the drawing board, others have materialised, while others still have turned into a process which moves in a different often opposite direction. A legacy as difficult, controversial and contradictory as this certainly deserves to be discussed and analysed.