The Shifting Dynamics: How Trump's Relationships with Putin and Zelenskyy Have Evolved Throughout His Second Term

President Trump's stance toward Putin and Zelenskyy has undergone significant transformation throughout his second term in office.

During his 2024 campaign, Trump consistently claimed he could end the Russia-Ukraine conflict "in 24 hours" if elected. However, ten months into his presidency, achieving peace has proven complex, with evolving relationships between Trump, Ukrainian President Volodymyr Zelenskyy, and Russian President Vladimir Putin.

Trump's early 2025 approach showed admiration toward Putin, but gradually shifted to expressing frustration with the Russian leader while softening his criticism of Zelenskyy following their February Oval Office confrontation.

The Trump administration implemented sanctions against Russia, and by autumn, Trump suggested Ukraine could reclaim all territory lost to Russian forces—a dramatic departure from his earlier position urging Kyiv to make concessions to end the war that began with Russia's February 2022 invasion.

By late November, Trump endorsed a peace plan widely viewed as favorable to Russia. Some Democratic senators suggested the proposal originated from Moscow, citing information from Secretary of State Marco Rubio. While the State Department denied this claim and Rubio maintained the plan was American-authored, European allies worried it was too accommodating toward Russia.

Trump subsequently resumed criticism of Zelenskyy, suggesting the Ukrainian leader showed insufficient gratitude for years of American military support. He also criticized European countries for inadequate economic pressure on Russia.

In January, Trump indicated his administration had engaged in "very serious" discussions with Russia, suggesting he and Putin might soon take "significant" action toward ending the conflict.

By February, Trump harshly criticized Zelenskyy on Truth Social, writing: "A Dictator without Elections, Zelenskyy better move fast or he is not going to have a Country left." This drew bipartisan criticism from Congress, where defending Ukraine has traditionally received support from both parties.

The relationship deteriorated further when Trump and Vice President Vance berated Zelenskyy in the Oval Office, accusing him of ingratitude after Zelenskyy questioned Vance about diplomacy with Putin. The heated exchange, broadcast globally, led to the cancellation of Zelenskyy's White House visit and raised questions about continued U.S. support. Days later, Trump temporarily paused military aid to Ukraine to pressure Zelenskyy toward peace negotiations.

Despite early tensions, Trump initially expressed confidence in Putin, telling reporters aboard Air Force One: "I don't think he's going to go back on his word. I've known him for a long time. We've always gotten along well."

However, Trump's stance hardened after Russia intensified attacks on Kyiv. On Truth Social, he wrote: "I am not happy with the Russian strikes on KYIV. Not necessary, and very bad timing. Vladimir, STOP! 5000 soldiers a week are dying. Lets get the Peace Deal DONE!"

In an ABC News interview following a meeting with Zelenskyy at Pope Francis' funeral, Trump acknowledged the human cost: "A lot of his people are dying. They're being killed, and I feel very badly about it." This signaled a shifting attitude toward the Ukrainian president after their earlier Oval Office dispute.

Trump's frustration with Putin grew evident when he posted: "I've always had a very good relationship with Vladimir Putin of Russia, but something has happened to him. He has gone absolutely CRAZY!"

Following a closed-door meeting with Zelenskyy during a NATO summit in The Hague, Trump described the Ukrainian leader as "very nice" and suggested he wanted to end the conflict, even opening the possibility of sending Patriot air defense missiles to Ukraine.

Trump's criticism of Putin intensified during a Cabinet meeting when he stated: "We get a lot of bull---t thrown at us by Putin, if you want to know the truth. He's very nice all the time, but it turns out to be meaningless." This occurred a day after announcing more weapons for Ukraine—reversing his earlier pause on military deliveries.

As Russia escalated aerial attacks, Trump told reporters: "I am very disappointed with President Putin, I thought he was somebody that meant what he said. He'll talk so beautifully and then he'll bomb people at night. We don't like that."

During an Oval Office meeting with NATO Secretary-General Mark Rutte, Trump pushed harder against Putin: "I don't want to say he's an assassin, but he's a tough guy. It's been proven over the years. He's fooled a lot of people before." Trump threatened "secondary tariffs" if no peace deal emerged within 50 days, targeting Russia's trading partners to isolate Moscow.

Despite arranging a summit in Alaska, Trump failed to secure an agreement from Putin, merely stating: "There's no deal until there's a deal." Critics noted that Trump had granted Putin international recognition despite years of Western efforts to isolate him over the war and human rights concerns.

Following a meeting with Zelenskyy at the UN General Assembly, Trump criticized Russia's military performance: "Russia has been fighting aimlessly for three and a half years, a War that should have taken a Real Military Power less than a week to win. This is not distinguishing Russia. In fact, it is very much making them look like 'a paper tiger.'" Notably, Trump suggested Ukraine could reclaim all territory lost to Russia—contradicting his previous position.

After hosting Zelenskyy at the White House again, Trump called to "Stop the war immediately" but implied Moscow might keep captured territory: "You go by the battle line wherever it is - otherwise it's too complicated. You stop at the battle line and both sides should go home."

Trump had spoken with Putin by phone before Zelenskyy's visit and announced plans to meet Putin in Hungary—a meeting that never materialized due to lack of progress. Trump also denied Ukraine's request for long-range Tomahawk missiles that Ukrainian officials believed could strengthen their negotiating position.

As the Treasury Department announced sanctions against Russia's largest oil companies, Trump expressed hope that "hopefully he'll become reasonable," referring to Putin, while adding: "And, hopefully Zelenskyy will be reasonable, too. You know, it takes two to tango, as they say."

Trump later pressured Zelenskyy to accept a peace plan involving land concessions to Moscow, massive reduction of Ukraine's military, and European agreement that Ukraine would never join NATO. Trump set a November 27 deadline for Zelenskyy's response but indicated more time might be allowed if progress toward peace continued.

When asked if this peace proposal was his final offer, Trump replied: "I would like to get to peace," suggesting flexibility beyond the deadline. "We're trying to get it ended. One way or the other, we have to get it ended."

Senators from both parties reported that Secretary Rubio told them Trump's plan resembled a Russian "wish list"—an account the State Department called "false" and which Rubio himself denied.

Most recently, Trump renewed criticism of Ukrainian leadership on Truth Social: "UKRAINE 'LEADERSHIP' HAS EXPRESSED ZERO GRATITUDE FOR OUR EFFORTS, AND EUROPE CONTINUES TO BUY OIL FROM RUSSIA." He maintained that with "strong and proper US and Ukrainian LEADERSHIP," Russia's invasion "would have NEVER HAPPENED," again blaming his predecessor Joe Biden for the conflict.