FRONTLINE traces Vladimir Putin's path from KGB officer to Russian president and his running conflict with four American presidents. Interviews with former U.S. officials, ambassadors, and journalists reconstruct the private meetings and public standoffs, from Bill Clinton's early attempts to bring Russia into the Western fold, through George W. Bush's claim to have looked into Putin's soul, to Barack Obama's reset policy collapsing after the invasion of Georgia and the seizure of Crimea. The film lays out how Putin tested each administration's response and adjusted his tactics accordingly, moving from regional aggression to interference in the 2016 U.S. election and finally to the full-scale invasion of Ukraine. Archival footage of summits, war zones, and campaign rallies is paired with firsthand accounts from people who sat across the table from him. The result is a chronological record of miscalculation on both sides, showing how a series of individually explicable decisions built toward a war that surprised the same officials who had spent decades watching him.