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Is a new grand bargain for European security needed? How can it be achieved? Would it last? These are questions often presented as the post-Cold War security order in Europe seems to be in tatters. This paper looks at these questions historically from the Russian perspective focusing especially to the Cold War and the end of it as well as the recent debate of a new security order including the Medvedev proposal. The paper will review the Russian thinking on these issues relying on recent historiography as well as draw on newly released archival material where possible. The paper argues that security grand bargains have always been a mixture of power, interests and normative principles, but the new order has more often been created by the adopted practice. The paper also discusses the lessons and perhaps also wrong lessons that the current Russian leadership and elite have drawn on the basis of the past grand bargains.