Snyder starts the Prologue of The Road to Unfreedom by recounting the challenging birth of his son in Vienna in 2010, a year he describes as one of reflection amid a slow recovery from the 2008 financial crisis. He recalls holding his newborn son and sending out email to his friends and acquaintances, including to a friend who boarded the plane going to Smolensk, which crashed. His account juxtaposes the celebration of new life and the mourning following the air crash, which killed all 96 passengers on board, including the Polish president at that time, Lech Kaczyński.

Snyder remembers his collaboration with historian Tony Judt, who was battling amyotrophic lateral sclerosis at the time that Snyder was working on a history book about political mass murders in Europe during the 1930s and 1940s. Judt and Snyder expressed worry about the American society taking democracy for granted. Judt had studied the role of intellectuals in facilitating totalitarianism in the past and saw a parallel in the contemporary dismissal of ideas, which leads to a dangerous weakening of democratic values and institutions.

Snyder reflects on his process of writing a history book about the mass murders in Europe during the 1930s and 1940s by Nazi Germany and the Soviet Union.