Standing beside President Vladimir V. Putin of Russia in Finland’s presidential palace on a midsummer’s day seven years ago, President Trump proved that he still had the power to shock.
At a news conference after meeting privately with the Russian leader, Mr. Trump sided with Mr. Putin on whether the Kremlin had meddled in the 2016 U.S. presidential election.
“President Putin says it’s not Russia. I don’t see any reason why it would be,” Mr. Trump said, contradicting his own intelligence officials before recounting discredited conspiracy theories.
Top Republicans were horrified. Senator John McCain called it a “disgraceful performance.” Mr. Trump’s own national security adviser at the time, John R. Bolton, would later write that “Putin had to be laughing uproariously at what he had gotten away with in Helsinki.”
Mr. Trump plans to see Mr. Putin on Friday in Alaska for the first time since his return to the White House to discuss the U.S. president’s goal of ending the war between Russia and Ukraine. With Mr. Putin pressing peace proposals that heavily favor Russia, many analysts and former Trump officials worry that he will once again turn a meeting with Mr. Trump to his advantage.
During Mr. Trump’s first term, he and Mr. Putin met six times in person and had several more phone conversations. (His successor, Joseph R. Biden Jr., met Mr. Putin only once, in June 2021, before the Russian invasion of Ukraine.)
Those interactions alarmed many of Mr. Trump’s senior aides, who watched as the U.S. president disregarded their advice, excluded them from meetings with the Russian leader and proposed impractical ideas that appeared to have been planted by Mr. Putin, like creating a U.S.-Russia “impenetrable Cyber Security unit.” The idea was dropped as soon as Mr. Trump got back to Washington.
The relationship has grown more complicated in Mr. Trump’s second term. In recent months Mr. Trump, eager to fulfill his promises of settling the war between Russia and Ukraine, has grown irritated by Mr. Putin’s unwillingness to de-escalate the conflict.
Mr. Putin will land in Alaska determined to rewind Mr. Trump’s view of the war to February, when he berated President Volodymyr Zelensky of Ukraine at a contentious White House meeting for not showing more gratitude for U.S. support, while speaking warmly about Mr. Putin.
“Since the blowup between Trump and Zelensky in the Oval Office, Europeans, Ukrainians and Ukraine’s supporters inside the administration have cobbled together a policy of helping Ukraine stay in the fight and preventing the lurch by Trump to embrace Russia’s view of the conflict,” said Andrew Weiss, the vice president for studies at the Carnegie Endowment for International Peace.
“The real test on Friday will be how much of that policy survives the first in-person contact between Trump and Putin in his second term,” Mr. Weiss added.
The White House portrays the meeting as an example of Mr. Trump’s dedication to stopping the bloodshed in Ukraine and defends his unconventional style as a needed break from slow-moving diplomatic customs.
But critics worry that the hastily planned conversation will play into the hands of Mr. Putin, a former K.G.B. agent known as a master manipulator.
“I think he believes he should reel Trump back in, and believes his K.G.B. skills will do that,” Mr. Bolton said in an interview with NewsNation last week.
The Russian leader may also benefit from the fact that Mr. Trump, in contrast to his first term, has few advisers pushing back against Mr. Putin’s worldview. For his trip to Helsinki, for instance, Mr. Trump was surrounded by such Russia hawks as Mr. Bolton, Secretary of State Mike Pompeo and Defense Secretary Jim Mattis.
Today, Secretary of State Marco Rubio is the lone member of Mr. Trump’s inner circle with a clear record of criticizing Mr. Putin. But even Mr. Rubio, who also serves as Mr. Trump’s national security adviser, has softened his tone since joining Mr. Trump’s cabinet.
The Alaska meeting was set after Mr. Trump’s special envoy, Steve Witkoff, met with Mr. Putin in Moscow last week. Mr. Witkoff, a friend of Mr. Trump and a fellow real estate mogul, had no diplomatic experience before joining government. He has been criticized for meeting with Mr. Putin without other U.S. officials and for echoing his talking points afterward.
To be sure, the Russia hawks around Mr. Trump in his first term often had little success. When Mr. Trump called Mr. Putin after the Russian president was re-elected in a March 2018 vote widely seen as illegitimate, Mr. Trump’s aides placed a clear instruction in his briefing papers: “DO NOT CONGRATULATE.” Mr. Trump did so anyway.
Not even a federal investigation into 2016 Russian election interference was enough to restrain Mr. Trump. When the two leaders last met in person, on the sidelines of a 2019 Group of 20 gathering in Osaka, Japan, Mr. Trump joked with Mr. Putin about the subject. “Don’t meddle in the election!” Mr. Trump said, with a smirk and a finger wag. Mr. Putin grinned in delight.
The investigation, and the presence of Putin critics at high levels of his administration, may have led Mr. Trump to conduct his conversations with unusual secrecy, however.
When the men first sat down together, at a Group of 20 summit in Hamburg, Germany, in 2017, Mr. Trump was joined only by his secretary of state, Rex Tillerson, and an interpreter. After the meeting, Mr. Trump took the interpreter’s notes and ordered him not to disclose what he heard.
That evening, Mr. Trump and Mr. Putin had an impromptu conversation, initiated by Mr. Trump, at a group dinner. No other Americans were present, and the White House confirmed the meeting only after surprised witnesses spoke to reporters.
Asked by reporters what he had told Mr. Trump in Hamburg about the 2016 election, Mr. Putin replied, “I got the impression that my answers satisfied him.”
For his part, Mr. Trump called a New York Times reporter in Hamburg just as he was departing from the summit meeting and said Mr. Putin had told him that Russia could not have been involved in the 2016 election because its operations were so sophisticated they never would have been detected. Mr. Trump said he was “very impressed” by that argument, a case he went on to make in public.
Analysts said they have low expectations for the sort of breakthrough on Ukraine that Mr. Trump is hoping to achieve in Alaska. Mr. Putin has shown every sign that he believes he can gain more on the battlefield than in negotiations — at least on the terms Mr. Trump has so far required.
Maria Snegovaya, a senior fellow for Russia and Eurasia with the Center for Strategic and International Studies, noted that in his first term Mr. Trump tried to strike major deals with the authoritarian leaders of such nations as China and North Korea, with limited results.
“In general, Trump’s history of meetings with strong men from Xi Jinping to Kim Jong-un does not lead to a successful deal that follows,” she said.
Fiona Hill, who was senior director for Europe and Russia on the National Security Council in the first Trump White House, agreed that any breakthrough appeared unlikely.
Mr. Putin and his aides have been frustrated at a lack of diplomatic progress with the Trump administration, and Ms. Hill said she sees little fresh ground for a deal, even one favorable to Mr. Putin.
The Russians “always want something they can take to the bank, an agreement they can hold the U.S. to,” she said. “They were excited by Witkoff at first, since he’s a direct channel to Trump, but they’re frustrated there’s no structure around it.”
While Mr. Putin might welcome a leader-to-leader meeting, she said, “he wants the details to be worked out later. And Trump isn’t a details guy.”
Edward Wong and David E. Sanger contributed reporting.
Michael Crowley covers the State Department and U.S. foreign policy for The Times. He has reported from nearly three dozen countries and often travels with the secretary of state.
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