Donald Trump’s Early Russia Entanglement: An Investigative Timeline

The Geopolitical Context (Late 1980s–Early 1990s)

In the late 1980s, the Cold War’s long chill was starting to thaw. Soviet leader Mikhail Gorbachev had risen to power in 1985 and introduced policies of perestroika (economic restructuring) and glasnost (openness). His approach was one of détente with the West – a “refreshing contrast to the global confrontation” of previous Soviet regimes (The Hidden History of Trump’s First Trip to Moscow - POLITICO Magazine). U.S. President Ronald Reagan, who had branded the USSR the “Evil Empire” in 1983, began engaging Gorbachev in high-stakes diplomacy. By 1987, Reagan and Gorbachev were negotiating major arms control agreements, such as the INF Treaty, even as Reagan maintained a hawkish posture. This era straddled tough anti-Soviet rhetoric and an emerging eagerness for rapprochement.

Globally, the Soviet Union was struggling—its centrally planned economy stagnating and its influence over Eastern Europe weakening. Gorbachev’s reforms aimed to modernize the Soviet system and ease tensions with t…