“I have NATO. I have the U.K., which is in somewhat turmoil. And I have Putin,” Donald Trump explained to reporters Tuesday on the White House lawn, laying out his itinerary before departing for Europe. “Frankly,” he predicted, before boarding his helicopter, “Putin may be the easiest of them all.” Those parting thoughts have turned out to be prescient: the United Kingdom is indeed in turmoil after Trump, having bashed NATO in Brussels, promptly ignited another diplomatic and political crisis in London. The diplomatic community had been hoping against hope that Trump might bolster the international alliance before jetting off for his alone time with the Russian president in Helsinki, to no avail. “What would be really great would be to have the allies united, strong, showcasing resolve with a big sense of purpose,” sighed Julianne Smith, a NATO vet who served as Joe Biden’s deputy national security adviser. Instead, she told me, “what we’re gonna have before he goes to meet Putin is a divided alliance, a contentious meeting, anger and frustration on all sides . . . for Putin, this is a real win.”

The more pressing fear, however, is what Trump will say or do when he and Putin meet on Monday, face-to-face. As The New Yorker’s Susan Glasser reports, preparations for the Helsinki summit have been unusually limited, prefaced only by National Security Adviser John Bolton’s single trip to Moscow last month. Even more alarming to foreign-policy experts, there is still no formal agenda for the meeting. Ordinarily, diplomats and aides would have established a list of “deliverables” ahead of such a high-profile event—especially one in which Trump is planning to first meet with Putin alone. Instead, according to Glasser, the Russians told Bolton, “The meeting is the deliverable.” Asked about their sit-down on Thursday, Trump signaled that his conversation with Putin would be unscripted, characterizing it as a “loose meeting.”

This, as a former senior State Department official told me last month, is the worst-case scenario for the Trump-Putin summit. “My concerns on such a summit revolve around the agenda. . . . While the ‘surprise’ value of starting with a Trump-Kim summit might have worked in the D.P.R.K. case, it won’t with the Russians,” this person said, referring to Trump’s June 12 meeting with North Korean dictator Kim Jong Un. “I’d want to see plenty of meetings—both internal U.S. and with Russian counterparts—at lower levels to talk through the whole range of issues with the Russians . . . But I worry that the style of this president may push toward a meeting that isn’t fully fleshed out. And, to my mind, that plays to Russia’s advantage.”

Trump, however, has apparently dismissed all efforts to constrain his dialogue with Putin, viewing their meeting as long overdue. “He thinks that they are two strongmen-minded leaders,” said a source familiar with previous administrations’ attempts to open a conversation with Putin. “He thinks that together they will be able to get through the clutter of the ‘deep state’ as he calls it and actually get things done.” Already, Trump has U.S. allies concerned. During his impromptu news conference on Thursday, the president didn’t rule out agreeing to cease NATO military exercises in the Baltics, or recognizing Crimea as part of Russia. “People like to say, ‘Oh Crimea,’ but the fact is they built bridges to Crimea, they built, I think, a submarine port,” Trump said. “What will happen with Crimea from this point, that I cannot tell you. But I am not happy about Crimea, but again that was Barack Obama’s watch, not Trump’s watch.”