On Thursday in Istanbul, the empty seat reserved for Vladimir Putin perfectly symbolized Russia’s unwillingness to end the war in Ukraine. Putin’s counterpart in the negotiations, Volodymyr Zelensky, had spent days calling on him to show up and face him. "We are ready to talk," the Ukrainian President said. "To end this war."

But Putin stayed away, demonstrating his disdain for the peace process and handing Zelensky a tactical victory. For the Russians, it was the latest in a string of diplomatic stumbles. President Donald Trump and his envoys have tried for months to engineer a ceasefire in Ukraine. Along the way, they have given Putin plenty of chances to steer the Americans into his corner. But the Russian leader missed every one of them.

The most valuable opportunity landed in Putin's lap on the last day of February, when Trump and Zelensky engaged in a bitter shouting match in the Oval Office. Relations between the U.S. and Ukraine faced a crisis after that, and Trump briefly cut off U.S. aid to Ukraine. His overtures to Moscow grew friendlier than ever. In the middle of March, Trump held what he described as a “very good and productive” phone call with Putin. His lead envoy in the peace talks, Steve Witkoff, visited Putin in Moscow and, upon his return, publicly echoed many of the Kremlin’s arguments about the war.

Watching from Kyiv, Zelensky grew worried that Putin had won over the Americans. “I think Russia managed to influence some members of the White House team through information,” Zelensky told TIME in an interview in Kyiv on March 21. “Their signal to the Americans was that the Ukrainians do not want to end the war, and something should be done to force them. Of course, that was disinformation. It’s not true.”But Trump appeared to be buying it. In early April, his administration welcomed Putin’s envoy, Kirill Dmitriev, who became the first senior Russian official to visit the White House in more than three years. Dmitriev, a former investment banker, offered the U.S. a series of lucrative mining deals and access to Russian natural resources in exchange for the lifting of U.S. sanctions. Trump seemed impressed. “Europe has not been successful in dealing with President Putin,” he told reporters after the visit from Dmitriev. “I think I will be successful.”

To all appearances, Putin was outwitting Zelensky in their competition for Trump’s good graces. But on April 13, just a few days after Dmitriev’s visit to Washington, the tide abruptly turned. Two Russian ballistic missiles struck the Ukrainian city of Sumy that morning, killing at least 34 people and wounding another 117, including 15 children. Television broadcasts around the world showed the bloodied bodies of the victims strewn across one of the city’s central squares, near the university. Less than two weeks later, as Trump and his team continued pushing for a peace deal and promising results, the Russians launched one of the deadliest bombing raids against the Ukrainian capital since the start of the war. Around 70 missiles and 150 drones struck Kyiv on the night of April 24, killing at least a dozen people and wounding scores of others.

That wave of attacks made Trump look naive, even foolish, for claiming that Russia was serious about the peace process, and his tone toward the Kremlin sharply changed. “Not necessary, and very bad timing,” Trump wrote on social media the day of the Kyiv bombings, adding a direct appeal to Putin: “Vladimir, STOP!”

The attacks against Kyiv and Sumy seemed wholly unnecessary, even for the advancement of Putin’s war aims. Striking civilians in northern Ukraine, far behind the frontlines, did nothing to help Russian forces advance in the east and south of the country, where they have been desperately fighting for years to seize more Ukrainian territory. It would have cost Putin nothing to halt the attacks against civilians and focus on military targets along the front lines, at least until he could cement his rapprochement with the Trump administration.

But the Russians couldn’t help themselves. Even as Trump and Zelensky called for a ceasefire of 30 days to clear the way for peace negotiations, Putin blew apart any semblance of good faith by continuing to massacre civilians. On the diplomatic front, the decision has cost him dearly. It created an opportunity for Zelensky to win Trump back to his side, and the Ukrainian leader seized it on April 26.