From 1987 Moscow real estate dreams to secret sanctions calls and hacked elections - this timeline lays it all out.
Some day, the full story of Trump and Russia will spill into the daylight.
Documents will be declassified. Whistleblowers will talk. What was once national-security catnip will eventually become history. But for now, Trump’s relationship with Russia remains a half-told story, shrouded in denials, investigations, and enough conflicting narratives to make your head spin.
Here’s what we do know — a timeline tracing Trump’s peculiar fascination with Russia, from his first Moscow trip in the 1980s to the scandals that shadowed his presidency.
The 1980s and 1990s: The Real Estate Hustle
1987: Trump visits Moscow and Leningrad, exploring hotel deals in the USSR. Nothing comes of it, but the seed is planted.
1988: Trump spreads a (false) rumor that Mikhail Gorbachev will visit Trump Tower. Instead, a Gorbachev lookalike shows up for a photo op.
1996: Trump returns to Moscow, trying to partner with a tobacco firm to build a hotel. Another dead end.
1997: Trump pitches a 40 million dollar bronze Columbus statue for New York’s Hudson River, created by a Russian artist. It never happens.
The 2000s: Russian Money Flows In
2005: Trump partners with Bayrock Group — a development firm linked to Russian investors and mobsters — to build Trump SoHo.
2007: Trump Jr. admits: “Russians make up a disproportionate cross-section of our assets.” In plain English: Russian money is propping up Trump’s projects.
2013: Moscow, Miss Universe & Aras Agalarov
Trump brings his Miss Universe Pageant to Moscow, partnering with oligarch Aras Agalarov. He floats more real estate deals, none of which materialize. Still, Trump calls Putin “a great leader” and tweets about wanting to be “best friends.”
2015-2016: The Campaign & Kremlin Courtship
• Trump hires Paul Manafort, whose past clients include Viktor Yanukovych, the pro-Putin former leader of Ukraine.
• Trump mentions obscure advisor Carter Page, who soon travels to Moscow for murky meetings with Russian officials.
• Russian hackers infiltrate the DNC and begin leaking damaging emails. Trump publicly invites Russia to hack Hillary Clinton’s emails.
• At the Republican National Convention, Trump’s team weakens the GOP platform’s support for arming Ukraine.
The Email Leaks & The Election
• July 2016: WikiLeaks dumps hacked DNC emails, embarrassing Democrats right before their convention.
• October 2016: WikiLeaks drips out John Podesta’s hacked emails, feeding a firestorm of anti-Clinton stories.
• November 2016: Trump narrowly wins the presidency.
2017: Scandals Erupt
• Michael Flynn resigns after misleading officials about his calls with Russia’s ambassador — specifically about sanctions.
• Congress opens investigations into Trump-Russia ties.
• The infamous Steele Dossier — full of unverified but explosive allegations (yes, including the “pee tape”) — becomes public.
What It All Means
Trump’s relationship with Russia isn’t one story — it’s dozens of strange threads woven together. Real estate dreams. Mob-linked partners. Backchannel calls. Campaign favors. Election interference. It’s not always clear what’s smoke and what’s fire.
But here’s what is clear: Russia saw Trump as an opportunity — to influence U.S. policy, to weaken NATO, to fracture democracy itself. Whether Trump was a useful idiot or a willing player is a debate for historians.
For now, the timeline speaks for itself.