Trump and Zelenskyy return to talks with few breakthroughs behind them

A complicated history of contacts

The leaders of the two countries spoke by phone back in 2019, during Trump's first term. Their conversation even led to an attempt to impeach the US president over pressure on Zelenskyy to assist with an anti-corruption investigation involving Hunter Biden. His father, Joe Biden, was Trump's main rival in the election.

Trump later lost the presidential race to Biden and largely withdrew from active politics for almost four years. When Trump launched another bid for the US presidency, Ukrainian diplomacy also began efforts to restore contacts with his team.

As a result, during the election campaign, the two leaders held an informal meeting at Trump Tower in New York on September 27, 2024.

After Trump was reelected for a second term but before his inauguration, he also met with Zelenskyy in Paris. On December 7, 2024, both leaders attended a ceremony marking the reopening of the restored Notre-Dame Cathedral. French President Emmanuel Macron acted as an informal mediator between them.

During Trump's second term

During his election campaign, Trump said he could end Russia's war against Ukraine within 24 hours. After his return to the White House, this became one of the key areas of his foreign policy. Zelenskyy's controversial visit to Washington on February 28, 2025, was focused on peace negotiations.

Trump attempted to pressure Zelenskyy into making concessions during a live televised exchange. During the discussion, he questioned whether Ukraine could win the war, pointed to a severe shortage of troops in the Armed Forces of Ukraine, and called for an end to the fighting.

Zelenskyy responded by accusing Moscow of ignoring previous agreements, which angered the US leader. The US president accused his Ukrainian counterpart of "gambling with World War III," and Vice President JD Vance later joined the heated exchange. Following the confrontation, Trump convened a meeting with his advisers in the Oval Office, while the Ukrainian delegation was asked to leave the White House early.

It remains unclear whether the confrontation was planned by Trump's team or was spontaneous.

A few months later, Zelenskyy and Trump somewhat improved their personal relationship. Their next meeting took place at the Vatican on April 26 during the funeral of Pope Francis.

During the ceremony, the Vatican even took the unprecedented step of breaking diplomatic protocol to seat the Ukrainian leader in the front row near Trump. This time, the two spoke one-on-one and without cameras. Apart from restoring personal contact, however, the conversation produced no visible results.

The two leaders next met in Washington on August 18 following Trump's summit with Russian leader Vladimir Putin in Anchorage. Accompanied by several European leaders, Zelenskyy discussed with Trump the proposals he had received from the Kremlin.

The White House meeting took the form of an emergency consultation but, according to diplomats, ended without any concrete or firm decisions on a settlement. Negotiations on ending the war subsequently moved to a lower level. A working group spent a long time preparing proposals, but that process eventually also faded away.

A new stage

After the meeting in Washington, Volodymyr Zelenskyy and Donald Trump did not meet in person for almost a year. A period of somewhat cooler relations ended only on July 8 this year, when they had a brief conversation in Ankara on the sidelines of the NATO summit. Once again, however, no concrete agreements were reached.

The leaders had another contact later that month, but under much sadder circumstances. On July 28, Zelenskyy traveled to the United States specifically to attend the funeral of influential US Senator and longtime friend of Ukraine, Lindsey Graham, where he once again crossed paths with the White House leader. The brief conversation was largely a matter of protocol and showed only that both sides were willing to maintain communication.

This time, despite increased contacts ahead of the current talks in New York, the outcome could be similar. An informed RBC-Ukraine source said that no breakthroughs are expected for now, but "the main focus is on energy de-escalation."

The only tangible result that could emerge from the meeting here and now is a joint statement that peace negotiations must be preceded by a complete and unconditional ceasefire, Aleksandr Leonov, executive director of the Center of Applied Political Studies "Penta", told RBC-Ukraine.

"In principle, the United States has gradually begun returning to this idea, which Trump proposed in early 2025 and then abandoned in Anchorage. US envoys at the UN and American diplomats are also talking about it," Leonov said.

As for other issues on the bilateral agenda, providing Ukraine with additional interceptors for Patriot air defense systems has become more difficult because of the latest escalation in the Middle East. Still, the very fact that the meeting is taking place is positive for Ukraine.

"Let's remember that just a few days ago, this meeting had not been confirmed. The White House was saying that no contacts were planned at all. But after the strikes on Moscow and the Moscow region, Trump called and confirmed the meeting," Leonov added.

At the same time, this does not mean that the conversation between the two leaders will be easy. The Guardian reported that Trump could pressure Zelenskyy during the meeting over attacks on Russian oil refineries.

More broadly, Donald Trump is approaching important US congressional elections, shifting his attention toward the domestic political agenda, while Vladimir Putin continues to show no desire to move toward a genuine end to the war. In this situation, Ukraine's push for a real end to the war remains "a voice crying in the wilderness."

Quick Q&A

– How many times have Zelenskyy and Trump met in person, and what were the results?

– The leaders have held five in-person meetings in total, beginning with an informal conversation at Trump Tower in September 2024 and the meeting at Notre-Dame in Paris. They later held talks in Washington, the Vatican, Ankara, and at Lindsey Graham's funeral in the United States.

– Why did Zelenskyy's visit to the White House in late February 2025 end in a scandal?

– During the Oval Office meeting, Donald Trump called for an end to the fighting and pointed to a shortage of personnel in the Armed Forces of Ukraine, accusing the Ukrainian leader of "gambling with World War III." In response, Volodymyr Zelenskyy stressed Russia's failure to comply with previous peace agreements, which angered Trump and his team. As a result of the dispute, the Ukrainian delegation was asked to leave the White House early.

– What can be expected from the Zelenskyy-Trump meeting in New York on September 22?

– The main topics of the talks on the sidelines of the UN General Assembly are expected to be energy de-escalation and protecting infrastructure from Russian attacks. However, sources and analysts do not expect breakthrough decisions or the signing of major agreements during the meeting.