Read: What does being Trump’s friend get you?

But Trump might be motivated by something else, his allies and administration officials suggest. They see Trump following a “good-cop, bad-cop” playbook that is meant to sustain a necessary dialogue with the leader of a nuclear-armed adversary. Leave it to Bolton, Pompeo, and others to deliver the harsh message, the argument goes. They will, and they have. Trump, meanwhile, will see to it that relations at the top stay cordial.

However, this interpretation assumes that Trump is operating not only with the best intentions, but also with a coherent strategy that belies his often improvisational, erratic style. And even if that were the case, such an approach has serious downsides: Trump winds up undercutting senior officials who are warning of dire threats that Russia poses to U.S. interests. Foreign leaders are never sure who speaks for the U.S. government. And there’s a real chance that Trump’s overtures will boomerang. Some experts predict that Putin, hardly a naif on the world stage, will use Trump’s evident desire for better relations to wrest concessions from the White House. All of which means that Pompeo is walking straight into one of the central contradictions of the Trump presidency: the gap between Trump’s words and the government’s deeds.

“The notion that you’re going to say nice things about [Putin] and he is going to change his ways, I don’t see any evidence that’s ever worked,” says Michael McFaul, the former U.S. ambassador to Russia during Barack Obama’s administration.

Administration officials say that perhaps, through personal diplomacy, Trump can coax Putin to meet U.S. goals, including dropping support for Nicolás Maduro’s regime in Venezuela and helping persuade North Korea to give up nuclear weapons. Still, some who’ve worked at the top levels of the administration concede that they’ve been baffled by Trump’s moves in the foreign-policy arena. How he gets his information isn’t always clear. Some have noted that Trump comes to briefings with ideas that seem to have sprung from private phone conversations with “people who want him to adopt a viewpoint that is sympathetic to Russia,” said one person familiar with the matter.

Trump has avoided one-on-one clashes with Putin, most recently when he failed to tell the Russian leader during their phone call that he must not interfere in the 2020 election. That wasn’t out of character. Trump’s habit has been to refuse to condemn Putin for election interference, most famously at a joint press conference in Helsinki over the summer. “The president keeps coming back to the point that if he’s not engaging, you can be sure there’s going to be estrangement [with leaders] at the very upper level,” said an administration official, who like others we spoke with requested anonymity to talk more freely about internal deliberations. “So he is constantly of the opinion that you have to have a good relationship at the top.”