American-Russian relations have been troubled from Lenin to Putin, from Wilson to Trump. Woodrow Wilson insisted that no one power should dominate Europe. This detailed analysis shows that Wilson was the first “Cold War Warrior,” and his “quarantine” policy toward Russia was the precursor of the policy the United States has generally followed toward Russia since the end of World War II. Wilson tried to avoid taking sides in the Bolshevik Revolution but finally was drawn into it from relentless Allied pressure. Yet he kept intervention minimal. Afterward, he quarantined communism until FDR recognized Russia and, later, allied with Stalin against Hitler. Truman and his successors renewed “quarantine,” calling it “containment.” With the USSR’s collapse, the shape and stability of Wilson’s Europe reappeared. The West has preserved that Europe through the EU, NATO, and sanctions against Putin’s restoring a Soviet sphere. America should now be clear, as Wilson once was, in supporting European security.