Like so many stories about Donald Trump, this one begins with a tweet.
More than a decade ago, Trump mused about whether Vladimir Putin would attend a beauty pageant that Trump was sponsoring in Moscow and, if so, whether Putin would “become my new best friend.” That seemingly random 2013 Twitter missive launched one of the most enduring and significant geopolitical bromances in recent times—one that has persisted despite election-interference allegations, a special-counsel investigation, and the invasion of Ukraine.
But in recent weeks, the relationship has begun to show signs of strain.
Exasperated by Putin’s reluctance to sign off on a cease-fire with Kyiv and by new images of violence in Ukraine, Trump has expressed rare public anger at the Russian leader while privately mulling a series of sanctions meant to force Moscow to the negotiating table. Trump has started to feel humiliated that Putin is, as the president said this week, “tapping him along,” and is frustrated that Putin does not seem to want to end the war, two outside advisers to the president and a third person familiar with the negotiations told us. At the same time, Trump said yesterday that he will wait “two weeks”—his favorite verbal crutch when stalling for time—before deciding on his next move toward Russia, raising the specter that the Trump-Putin relationship will survive.
The two-week time frame also postpones a potential inflection point in the Ukraine war: Will the president walk away from the conflict, which would bolster Russia? Or will he, for the first time, truly stand up to Putin?
“I do detect signs that he’s trying to put some blue water between himself and Putin. He thought because they were good friends he could wrap up the deal in 24 hours. Obviously none of that came close to being true,” John Bolton, Trump’s former national security adviser, told us. “Now Putin has started to push him a little bit. They’re starting to mock him.”
This is not how Trump thought it would go. He has long been impressed by Putin and his strongman’s grip on power, and he worked hard to establish a relationship with his Russian counterpart. During Trump’s first term, the pair met on multiple occasions without any staff present, a departure from protocol. And, infamously, Trump sided with Putin over his nation’s own intelligence agencies when asked during a 2018 Helsinki summit about Russian interference in the U.S. election two years earlier.
During his time out of office, Trump praised Putin as a “genius” and said repeatedly that, once back in the White House, he would settle the Russia-Ukraine conflict in a single day. He has since sought a summit with Putin that could turn into a made-for-TV moment to announce the end of the war—and a long-coveted Nobel Peace Prize for himself. (“He really wants a Nobel Peace Prize,” Bolton told us. “He’ll take it for Ukraine, he’ll take for Gaza, he’ll take it for Pakistan-India. He’s not particular.”) In his early months in office, Trump has been eager to make business deals with Russia and blamed Ukraine for somehow instigating a war that actually began when Russia deployed its military across the border. He berated Ukrainian President Volodymyr Zelensky in the Oval Office and temporarily cut off U.S. intelligence sharing and military aid, allowing Russia to make gains on the battlefield.
He also claimed that Ukraine—and specifically its leader—was the biggest obstacle to peace. Trump has flashed deep antipathy toward Zelensky, whom he deems ungrateful for U.S. support and at least partially responsible for his 2019 impeachment. (Trump withheld military aid from Ukraine to pressure Kyiv to investigate the family of his political rival Joe Biden.) In an Oval Office interview with The Atlantic in late April, when he was asked if there was anything Putin could do that would make him say he was on Zelensky’s side and not Putin’s, Trump again underscored his fraught relationship with the Ukrainian leader: “Not necessarily on Zelensky’s side, but on Ukraine’s side, yes,” the president said. “But not necessarily on Zelensky’s side. I’ve had a hard time with Zelensky.”
Yet in March, Zelensky quickly agreed to a new U.S. proposal for a 30-day cease-fire. Russia stalled in doing the same. More than two months later, Moscow still has not agreed to a pause in the fighting and instead has escalated the violence, unleashing waves of drone and missile attacks on Ukrainian cities in recent weeks, killing more than a dozen people.
That onslaught was the latest act of defiance from Putin, coming days after he skipped a possible meeting with Zelensky and Trump in Istanbul and then blustered through a two-hour call with the American president without agreeing to a cessation in hostilities. On Sunday, Trump bemoaned Putin’s defiance, writing on Truth Social, “I’ve always had a very good relationship with Vladimir Putin of Russia, but something has happened to him. He has gone absolutely CRAZY!” A Kremlin spokesperson, Dmitry Peskov, responded by musing that Trump was having “emotional reactions.”
Trump initially believed that Russia was willing to negotiate, according to the person familiar with the negotiations, who was granted anonymity to discuss sensitive internal conversations. But once Ukraine accepted the cease-fire proposal, “it was almost like calling the Russians’ bluff, and it’s clear at this point Putin is playing a delay tactic and the president finds it very frustrating,” the person said. “He’s genuinely frustrated that he thought Putin was in a place to have meaningful dialogue and seems to have reversed course.”
Despite Trump’s claim, there is little evidence that Putin has changed in some way; the KGB officer turned dictator has a long history of deceit. For more than a year, the United States and its allies have assessed that Putin is not willing to negotiate an end to his war in Ukraine, because he thinks he’s winning. Multiple intelligence evaluations have reached the same conclusion: For Putin, negotiating would mean giving something up—for example, ceding territory or agreeing to let Western powers continue to arm Ukraine. Putin is simply not willing to do that. And he likely believes now—with some justification—that he is successfully disrupting the NATO alliance and dividing Kyiv from Washington, according to intelligence officials in the United States and Europe.
Trump, who hates scenes of war, has been disturbed by recent images of dead Ukrainian civilians, including children, according to the two outside advisers, who were granted anonymity to discuss private conversations. Had Putin accepted Trump’s cease-fire offer instead of ratcheting up Russia’s attacks, Trump believes, those killings could have been prevented. It would not be the first time that gruesome images have spurred him into action. In 2017, Trump ordered missile strikes on a Syrian air base after he was shown what he said were “horrific” images of dead children killed by chemical weapons days before. Months later, he delivered a rare rebuke of Saudi Arabia after he was presented with photos of Yemeni children who were at risk of starving to death because of a blockade ordered by Riyadh.
In Trump’s first term, his administration sanctioned Moscow for a variety of misdeeds, including sponsoring election interference and cyberhacking, but the president himself has long been reluctant to punish Russia in any meaningful way. Although Trump has in recent days talked with aides about unleashing new sanctions against Russia, he is waiting to see what happens when representatives from Ukraine and Russia meet for a second round of talks, set for next week in Istanbul; the U.S. is not planning to send a delegation, but White House aides said Trump wants to see progress.
“The president is mad, but he also wants a deal,” one of the outside advisers told us. “He’s trying to figure out the best path to get there—but believe him when he says he’ll walk away.”
Republican Senator Lindsey Graham of South Carolina, a Trump ally, has co-sponsored a bill with Democratic Senator Richard Blumenthal of Connecticut that would impose more sanctions against Russia—as well as secondary sanctions against other nations that do business with Moscow—if Putin does not commit to peace talks. The measure now has the support of a bipartisan group of more than 80 senators, a veto-proof majority. But the White House is worried about a global rise in gas prices if stringent measures are put in place, an administration official and one of the outside advisers told us. Some in the administration are also leery of secondary sanctions, which could anger U.S. trading partners that purchase Russian energy, including China and India.
“President Trump inherited the brutal Russia-Ukraine war from Joe Biden, and has put forth great effort to solve it, in order to save lives,” White House Press Secretary Karoline Leavitt told us in a statement. “The President is hopeful this war will soon be solved and if it is not—he has options on the table.”
If a frustrated Trump fully walks away from trying to bring an end to the conflict, that decision will almost certainly work to Russia’s advantage. Without pressure from Washington to negotiate, Russia is likely to further escalate its violence. (Moscow’s recent uptick in attacks came after Trump had said he might abandon talks.) If the Trump administration also decides to stop sharing intelligence or aid with Ukraine, then the momentum of the conflict could shift dramatically. Europe would bear more of the responsibility for supplying Ukraine with weapons and guaranteeing its security. Although the continent has rallied around Ukraine since the war began, European militaries cannot match the ability of the United States to fortify Kyiv.
“This is hardly the art of the deal—effectively telling Putin that if he doesn’t engage in serious negotiations, he will suffer no costs and get everything he wants,” Rebecca Lissner, a former deputy national security adviser to Vice President Kamala Harris, told us. “This is not particularly surprising, as Trump is perennially reluctant to get tough with Putin.”
Despite the recent tension with Trump, Putin has gotten nearly everything he has wanted from Washington since Trump returned to the presidency in January. Trump has weakened U.S. soft power around the world and feuded with traditional allies. If Trump were to walk away from talks now, or fail to follow through on his threats to punish Moscow, he’d yet again be helping the man who in many ways did become his friend.
Shane Harris contributed reporting.
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