The agenda remains a mystery, as still does the outcome of their last meeting, nearly a year ago in Finland. "The whole world was watching in Helsinki when President Trump sided with Putin over his own intelligence community and we still, all this time later, don't know what they discussed in their private meeting," said Michael McFaul, U.S. ambassador to Russia under President Barack Obama. "And now, I suspect, they will bond over the end of the Mueller probe and push the narrative, individually and together, that there was nothing there. It will feel like a vindication to them both."
The Group of 20 summit in Osaka will be the leaders' first meeting since special counsel Robert Mueller ended his investigation with no finding that the Trump campaign in 2016 conspired with Russia. That question long had shadowed Trump's presidency.
Putin has denied that Russia meddled in the American election to help Trump win, even though Mueller uncovered extensive evidence to the contrary. That included a Russian military intelligence operation to break into Democratic Party emails and efforts by a "troll farm" to spread divisive rhetoric and undermine the U.S. political system by using phony social media accounts.
The current tensions with Iran are certain to be a meeting topic. Trump last week called off airstrikes to retaliate for Iran's destruction of a U.S. drone hours after Putin said the use of U.S. force in the region would trigger a "catastrophe."
Putin's defense of Tehran is not the only authoritarian government that he has backed. Putin has supported Venezuela's Nicolas Maduro and Syria's Bashar Assad, helping keep each in power despite American opposition. Moscow's deepening ties with China also have unnerved many in Washington.
For years, Trump has raised eyebrows with his effusive praise of Putin. The Russian president has steadfastly refused to criticize Trump, saying Russia-U.S. relations have become hostage to American political infighting and its "deep state."
"Even if the president wants to take some steps forward, to discuss something, there are plenty of restrictions coming from other state structures," Putin said in a radio call-in event last week, adding that he believed Trump's re-election bid will further tie his hands. "Dialogue is always good and necessary. If the American side shows interest in that, we are naturally ready for a dialogue as much as our partners are."
The leaders last year announced their withdrawal from a key arms control pact, the 1987 Intermediate-Range Nuclear Forces Treaty. It is set to terminate this summer, raising fears of a new arms race. Another major nuclear agreement, the New Start treaty, is set to expire in 2021 unless Moscow and Washington negotiate an extension.
"The relationship between the two nations is in poor shape by any measure and the administration policy toward Russia is relatively tough even though the president's rhetoric is not," said Richard Haass, president of the Council on Foreign Relations. "There is nothing teed up to succeed at this meeting."
Along with arms control frictions, Russia's annexation of Crimea and its support for a separatist insurgency in eastern Ukraine weigh heavily on Russia-U.S. relations. Last November, Trump abruptly canceled a scheduled round of talks with Putin on the sidelines of a summit in Argentina, citing Russia's seizure of Ukrainian navy ships and their crews. The two men briefly spoke later.
Putin's primary goal is to get Trump to ease sanctions that Congress has stepped in and toughened. Putin acknowledged last week that U.S. and European Union sanctions have cost Russia an estimated $50 billion since 2014. That has helped weaken Putin's hand and reduced his hopes for some grand bargain that would elevate Russia's power around the globe.
As for Trump's aims, "it's hard to know what the White House's goals are because this is not a normal administration," said Kimberly Marten, political science chair at Barnard College. "If it were, you could imagine progress being made on New Start treaty and arms control, while also trying to avoid conflict escalation in areas where their interests oppose, like Iran, North Korea, Venezuela and Ukraine. But I am not sure what the purpose of the meeting is."
All of Trump's meetings with Putin have raised questions. At their first one, in Germany in 2017, Trump took his interpreter's notes afterward and ordered him not to disclose what he heard to anyone. Trump later sat next to Putin at dinner without any American witnesses. That fall, in Vietnam, Trump listened to Putin's denials about interfering with the 2016 election.
And last July, Trump and Putin spent more than two hours in a private meeting in Helsinki with only their interpreters present. Some U.S. intelligence officials were never briefed on the discussions. On Monday, the chairman of the House Oversight and Reform Committee, Rep. Elijah Cummings, D-Md., said the White House never responded to a February letter asking what happened to records of the discussion.
At the news conference that followed the Helsinki summit, Trump responded to a reporter's question by declining to denounce Russia's election interference or side with his own intelligence agencies over Putin. Last week, when asked on NBC if he would warn Putin not to interfere in the 2020 election, Trump offered "I may." He made no promises to push to safeguard the American vote.
"This meeting, like their others, feels fraught with uncertainty," said McFaul.
Isachenkov reported from Moscow. Associated Press writer Mary Clare Jalonick in Washington contributed to this report.
Follow Lemire on Twitter at http://twitter.com/@JonLemire and Isachenkov http://twitter.com/@visachenkov