The article examines the reasons behind the sweeping rejection of liberal values in Russia. The author considers the legacy of the renowned literary critic, philosopher and journalist I. Dedkov (1934–1994), who, in the early 1990s, described the germ of what would become a crisis of liberalism. Having spent his life in a permanent situation of ‘the ever-shrinking space of the last freedom,’ Dedkov embraced liberalism as a key component of his belief system. He often likened freedom to life, arguing that one is inseparable from the other. During the years of transformation, Russia had no shortage of liberals, but hardly any one of them, theorists or practicians alike, was quite as knowledgeable as Dedkov was about the type of liberalism most likely to take root in Russia. A witness and active participant of the 1980s — 1990s events in Russia, Dedkov left behind a compelling analysis of a process that started as liberation, went through a series of bumblings about, deceit and self-deceit, all the way to the predictably dismal ending. Even though it has been a long time, Dedkov’s old projections and premonitions can throw light on today’s events and are likely to remain pertinent for years to come.