The ups and downs of Trump and Zelensky meetings

Ukrainian President Volodymyr Zelensky and US President Donald Trump have had their ups and downs since Mr Trump returned to the White House almost two years ago.

Their meeting later today on the sidelines of the United Nations General Assembly (UNGA) in New York will be their fifth since a disastrous encounter in the Oval Office in February 2025.

Subsequent meetings between the two leaders have gone much better.

Mr Trump went from echoing Russian claims and calling Mr Zelensky "a dictator without elections" a week before that February 2025 meeting to pressurising him to sign a peace deal in a series of angry social media posts, before eventually praising the Ukrainian president on several occasions later last year.

Mr Zelensky has learned how to deal with Mr Trump the hard way during that first Oval Office meeting: come with a smile on your face and don't take the bait.

Two months later, a photograph of the two leaders in St Peter's Basilica on the day of Pope Francis’s funeral captured a sense of mutual respect between the two men.

After that meeting, Mr Trump turned to criticising Russian President Vladimir Putin in his social media posts for a few brief weeks.

When the Ukrainian president returned to meet Mr Trump in the Oval Office in October 2025, it was all smiles.

Mr Zelensky wore a smarter suit and outwitted the same American reporter who had put him on the spot with a pointless question about his attire at the previous meeting.

The body language between the US and Ukrainian presidents may have improved and Mr Trump no longer berates Mr Zelensky on Truth Social as he did last year.

However, almost one year on from their last face-to-face meeting in Washington, the war is no closer to ending.

Russian President Vladimir Putin is sticking to the same demands to end the war that he made in June 2024: a Ukrainian withdrawal from Donbas, as well as the regions of Zaporizhzhia and Kherson.

US security guarantees for Ukraine remain undefined and supplies of US military aid to Ukraine have been reduced to a trickle compared to 2024, particularly the supply of US Patriot systems which have affected Ukraine’s ability to defend its skies against increasing Russian ballistic missile strikes.

While the US focused on its war with Iran, the air war between Russia and Ukraine escalated over the summer months.

Both sides continue to inflict significant damage to each other’s economies with massive drone strikes.

Ukrainian drone strikes on Russia’s oil refineries and retail warehouses since May have given Kyiv more leverage.

Mr Trump asked Mr Zelensky last week during a phone call to pause Ukrainian strikes on Russian refineries given the pressure that global oil markets are currently facing.

In today's meeting in New York, it is likely that Mr Trump will again press Mr Zelensky to call off strikes on Russian oil refineries.

But it is hard to see the Ukrainian president agreeing to that request without Russia agreeing to a reciprocal ceasefire covering energy infrastructure.

It is worth remembering that it was Ukraine that first proposed a halt to strikes against energy infrastructure early last year.

Only last week, Mr Trump said that both Russia and Ukraine had agreed to stop striking each other's energy but that did not materialise.

Kyiv again said that it was ready to halt such strikes if Moscow agreed to do the same.

Yet, Russia did not make its position clear on the proposal.

Russia's state news agency has reported that US Secretary of State Marco Rubio will meet with Russian Foreign Minister Sergey Lavrov at the UNGA tomorrow.

Even if Mr Trump and Mr Zelensky agree to a formula today to get an energy ceasefire in place, Mr Rubio will still have to relay the terms to Mr Lavrov tomorrow.

Given the Kremlin's past form, a fast response is not to be expected.

Whether Russia wants to halt strikes on Ukraine's energy sector ahead of the winter is also debatable.