As a Cold War high school freshman, CNN’s Jill Dougherty became fascinated by Russia—a passion that shaped her life and career. Over five decades, she studied in Leningrad, lived in Moscow, and reported on Gorbachev, Yeltsin, and Putin. Once hopeful about Putin’s promise as a reformer, she watched him become an authoritarian who crushed dissent and invaded Ukraine. This talk follows the country’s dramatic transformation through the eyes of an American who witnessed it firsthand.