From the perspective of a life-long academic who became U.S. Ambassador to Germany, I offer reflections on my diplomatic experience and how it illuminates major threats to American democracy and our allies today. As the only survivor of a generation of German Jews, I also reflect personally on how my own family’s trajectory is a story of the destructive weight of autocracy, the redeeming power of democracy, and the urgency of this perilous moment in history. In conclusion, I offer three broad strategies—requiring civic courage, sooner not later—to reverse the potential demise of democracy and to protect the people democracy must serve to survive.