U.S. President Donald Trump’s relationship with Russian President has been … interesting, to say the least.
Their relationship is such that there are dozens of markets on Polymarket which traders have been looking into: Will Putin meet with Trump before July? (12%) Will Trump visit Russia before July? (1%) Will Trump talk with Putin before July? (38%) and so on.
Most recently, Trump said Putin “has gone absolutely CRAZY!” amid continued attacks on Ukraine — more than three years after Russia began its invasion. It was a big enough tonal shift to make headlines, given Trump’s previous statements about his Russian counterpart.
So, what started as flattery has turned into a geopolitical tightrope walk — with the world watching. Donald Trump and Vladimir Putin have been circling each other for over a decade now, weaving between admiration, denial, confrontation, and chaos.
Let’s check out some key moments in their relationship.
The Moscow Encounter (2013)
Trump lands in Moscow for the Miss Universe pageant and starts eyeing a bigger prize: a Trump Tower in Putin’s playground. He tweets that he “can’t wait” to meet the Russian leader. They don’t actually meet — at least not officially — but the admiration tour begins.
2015–2016 – Campaign Trail Flattery
On the trail, Trump treats Putin like a strongman crush. He calls him a “strong leader,” tosses shade at Obama, and eats up the compliment when Putin calls him “colorful.” Meanwhile, Russian bots and hackers start warming up in the wings.
July 2016 – “Russia, If You’re Listening…”
Trump goes live and invites Russia to dig up Hillary Clinton’s emails — on national television. The kicker? Russian hackers reportedly launch attacks the very same day. Not subtle. Not smart. But definitely on brand.
January 2017 – Spy Games Confirmed
U.S. intelligence drops the hammer: Russia interfered in the 2016 election to help Trump. Trump nods, shrugs, then calls the whole thing a “witch hunt” while still kind of admitting, yeah, maybe Russia did something. Maybe.
July 2018 – Helsinki Summit
Trump meets Putin in Helsinki and practically hands him the keys to the narrative. Standing beside him, Trump says he doesn’t see “any reason” Russia would’ve meddled in the election — directly undercutting U.S. intel. The backlash is swift, brutal, and bipartisan.
2020 – Still Swooning
Even as reports surface that Russia put bounties on U.S. troops and poisoned opposition leader Navalny, Trump sticks to his script. He dodges criticism of Putin and doubles down on the bromance, calling the Russian leader “very smart.”
2021–2024 – Post-Presidency Praise
Out of office but still tweeting like he’s on the clock, Trump continues his long-distance love letter to Putin. After the Ukraine invasion, he calls Putin’s moves “genius.” The world groans. Critics call it what it is: gross.
February 2025 – Backchannel Diplomacy
Trump and Putin hop on a call and agree to start negotiations to end the war in Ukraine. But instead of bringing Ukraine to the table, Trump plans a summit in Saudi Arabia — and excludes Kyiv entirely. Critics call it a Putin-friendly stunt.
February 2025 – The Saudi Summit
Delegations from the U.S. and Russia meet in Riyadh. Ukraine? Not invited. Europe? Also sidelined. Trump floats the idea that Ukraine bears some blame for the war — a move that triggers outrage in NATO and among his own advisors.
February 28, 2025 – Oval Office Blow-Up
Trump meets with Zelenskyy in the White House. It goes south fast. Trump and Vice President J.D. Vance lay into him. Zelenskyy fires back. The meeting ends in a deadlock — no handshake, no statement, no plan forward.
March 2025 – Aid On Ice
Following that chaotic sit-down, Trump halts military aid and intel sharing with Ukraine. The pause sends shockwaves through Europe. Under pressure, aid is quietly restarted by the end of March — but the damage is already done.
May 2025 – Putin Pushes, Trump Snaps
As Russia ramps up missile and drone attacks on Ukraine, Trump breaks from his usual script. He calls Putin “absolutely crazy” and warns he’s “playing with fire.” It’s the sharpest criticism he’s ever thrown at the man he once called brilliant.
