President Donald Trump heads into a high-stakes meeting with Russian President Vladimir Putin on Friday, pursuing his expressed desire to improve relations with Moscow amid the radioactive politics around the Kremlin’s interference in the 2016 election.
The sit-down, scheduled for Friday afternoon at the G-20 summit in Hamburg, comes after years of praise from Trump for Putin—dating to at least 2013, when Trump asked in a tweet whether Putin will “become my new best friend” after Trump publicly invited the Russian to attend his Miss Universe contest in Moscow.
Since then Trump has called Putin “tough” and “strong,” repeatedly said he is “outsmarting” the U.S., and speculated that he’d “get along very well” with the Russian leader.
Along with the praise has come an unwillingness to criticize Putin personally—including for authorizing a Kremlin plan to influence the 2016 U.S. presidential election on Trump’s behalf. That Putin did so is an accepted fact among top U.S. intelligence officials, but one Trump continues to question, including during his Thursday stop in Poland.
Last week, National Security Adviser H.R. McMaster said Trump would come to the meeting with “no specific agenda,” sparking concern among Russia experts and former U.S. officials that Putin, a former KGB officer who recruited spies, might have an upper hand to manipulate Trump.
“The biggest challenge in these meetings is Putin’s tendency to try to run out the clock with history lessons and litanies of Russian grievances, so you’re constantly playing defense. The art is absorbing this, pushing back on the rhetoric only where essential, and then shifting to the topics you actually want addressed. That’s why going in without an agenda is so damaging,” said Jon Finer, who served as chief of staff to former Secretary of State John Kerry and has attended meetings with the Russian leader.
“It’s a recipe not just wasting time, but having the entire conversation on his topics and his terms,” Finer added.
The two men are scheduled to meet for 30 minutes, and will reportedly be accompanied only by their top diplomats—Secretary of State Rex Tillerson and Russian Foreign Minister Sergei Lavrov—and translators.
As CEO of ExxonMobil, Tillerson struck major oil deals with Putin, who personally awarded Tillerson Russia’s Order of Friendship medal, the highest honor Moscow can bestow on foreign citizens. Tillerson also met with Putin during an April visit to Moscow.
Lavrov and Russia’s ambassador, Sergey Kislyak, visited the Oval Office in May, the day after Trump fired former FBI director James Comey, who had been overseeing the investigation into contacts between Trump associates and Moscow during the election. American reporters were barred from the meeting, but Russian state news subsequently embarrassed the White House by releasing official Russian photographs showing Trump smiling and laughing with the Russian envoys.
American presidents have a fraught history with the Russian leader.
After a 2001 visit with Putin, George W. Bush approvingly declared that he was able to “get a sense of his soul” and even dubbed him “Pootie-Poot,” before later condemning the Russian as a brutish aggressor.
Barack Obama initially criticized Putin before meeting him in July 2009 and declaring that the Russian was “doing extraordinary work on behalf of the Russian people.”
Like Bush’s outreach, Obama’s attempt at a Russia “reset,” featuring cooperation on international issues like the Iran nuclear deal, largely collapsed. Most observers now agree that U.S.-Russia relations are at their lowest point since the end of the Cold War.
Trump is not alone in believing that the U.S. and Russia should get along better. In a recent meeting with reporters, William Perry, who served as Defense Secretary under President Bill Clinton, said that Washington and Moscow “need a constructive relationship” on issues like limiting and security nuclear weapons and materials.
In an unusual Wednesday statement that may have been an effort to shape Friday’s meeting, Tillerson urged Moscow to cooperate more closely with the U.S. in the fight against the Islamic State in Syria, including through the possible establishment of no-fly zones in the country.
Syria has been a sore point of relations between the Trump administration and the Kremlin. Tillerson, McMaster and other top Trump officials have criticized Putin for his de facto alliance with Iran in support of Syrian President Bashar Assad.
During his Thursday address to the Polish people in Warsaw, Trump invited Russia to end “its support for hostile regimes—including Syria and Iran—and to instead join the community of responsible nations in our fight against common enemies and in defense of civilization itself.”
Few analysts believe Putin will abandon his longtime client, Assad, anytime soon. But Putin might seek to echo that language, which echoes his own longtime call for the U.S. and Russia to set aside differences in the name of fighting terrorism.
Some Trump allies held out the possibility that Trump might confront the man he has spent years complimenting.
“I would hope what he would do is hand him a list of the issues we have with their country. And I think he may well do that,” Senate Foreign Relations Committee chairman Bob Corker told reporters this week.
On Thursday, Trump’s critics were more interested in whether he would stand up to Putin.
“President Trump must have the courage to raise the issue of Russian interference in our elections directly with President Putin, otherwise the Kremlin will conclude he is too weak to stand up to them,” said Adam Schiff, the ranking Democrat on the House Intelligence Committee said in a Thursday statement. “That would be a historic mistake, with damaging implications for our foreign policy for years to come.”
And if he doesn’t, Putin is likely to take note, said Finer: “Anything Trump doesn’t raise, like, for example, the election interference, can be assumed not to matter that much to him.”