In October 2015, four months after he had announced his White House bid, Donald Trump was asked how he would stare down Russian President Vladimir Putin, who had seized Crimea and sent troops into eastern Ukraine.
“It's a question of respect, just like deals,” Trump said on CNN. “I do deals. That's what I do. I do really good at deals.”
Trump did not disclose that he was quietly negotiating just such a deal — to build a luxury hotel and condominium complex in Russia, signing a letter of intent that month for a Trump Tower Moscow. The push for the project didn’t end until June 2016, after he had locked up the Republican presidential nomination.
Over those eight tumultuous months, Trump repeatedly called for upending U.S. foreign policy toward Russia and suggested easing economic sanctions imposed on Putin’s government for its aggression in Ukraine.
Federal court documents filed Thursday, when Trump’s former lawyer Michael Cohen pleaded guilty to lying to Congress about the Moscow project, raise questions about whether Trump was acting in the national interest — or his own — when he called for a dramatic change of U.S. strategy toward Russia.
The case was filed by special counsel Robert S. Mueller III, who is investigating Trump’s inner circle and Russian efforts to sabotage the U.S. election by releasing hacked Democratic Party emails and spreading disinformation on social media. U.S. intelligence agencies have concluded that the Kremlin-backed operation sought to get Trump elected.
Since taking office, Trump’s relations with Putin have puzzled — and often alarmed — national security officials and close allies.
In July, at a summit in Helsinki, Finland, Trump said he believed Putin’s denials of interfering in the election over the conclusions of his own government, spurring a storm of criticism and prompting his director of national intelligence to contradict the president and publicly affirm the assessment.
On Thursday, Trump abruptly scrubbed a meeting with Putin planned for Saturday on the sidelines of the Group of 20 summit in Buenos Aires. He cited, but did not criticize, Russia’s seizure of three Ukranian naval vessels and 24 crewmen last Sunday.
During the campaign, Trump stood alone in his embrace of Russia, challenging Republican orthodoxy and longstanding U.S. foreign policy.
He praised Putin repeatedly, downplayed the need for sanctions and called for a “unified front” with Russia in Syria’s civil war, ignoring bipartisan thinking that Putin should be reined in across the Middle East, not bolstered.
Trump also took aim at some of Putin’s favorite Western targets, including the European Union and the NATO military alliance, which Trump called “obsolete.” He also bragged that he and Putin were featured on the same episode of “60 Minutes,” although they appeared on separate segments.
“That was their highest-rated show,” he inaccurately boasted later in Iowa. “I was on with Putin. We looked very nicely together.”
While Trump was lavishing praise on Putin, his New York lawyer was working behind the scenes to make Trump Tower Moscow a reality.
On Jan. 26, 2016, Trump told Fox News that he wished the U.S. had a better relationship with Russia to help fight Islamic State terrorists in Syria. "Wouldn't it be nice if we actually got along with Russia?” Trump said.
Earlier that month, Cohen had reached out to Dmitry Peskov, Putin's press secretary, to talk about Trump’s plans. Cohen later spoke over the phone with Peskov’s assistant and "requested assistance in moving the project forward, both in securing land to build the proposed tower and financing the construction," according to a court document.
Trump declared himself the “presumptive nominee” on April 26 after he swept a series of major primaries and appeared on the verge of vanquishing all 16 opponents for the Republican nomination.
“We're going to have a great relationship with Putin and Russia,” he told reporters at Trump Tower in New York that day.
One week later, Cohen traded emails with Felix Sater, a Russian-born Trump business associate, about arranging trips to Moscow before and after the Republican National Convention in Cleveland that July to help lock down the real estate deal.
“My trip [will be] before Cleveland,” Cohen wrote, according to the court document. Trump would go “once he becomes the nominee after the convention.”
In the end, Cohen told Sater on June 14 that neither he nor Trump would visit Moscow, and the project died. The Washington Post reported the same day that a Democratic National Committee computer server had been hacked, a breach that was later determined to be part of Moscow's covert support for Trump's candidacy.
Trump’s praise for Putin’s Russia was not new. He had begun trying to build a tower in Moscow since before the Cold War ended. He had made multiple trips to Moscow over the years, including staging the 2013 Miss Universe contest there.
“Look at Putin, what he's doing with Russia,” Trump told Larry King in 2007. “Whether you like him or don't like him, he's doing a great job in rebuilding the image of Russia and also rebuilding Russia, period.”
Thomas Wright, director of the Center on the United States and Europe at the nonpartisan Brookings Institution, said Trump appears drawn to Russia’s macho culture and the sense that it’s a good place for those savvy or tough enough to navigate its bureaucracy and corruption.
“We know he’s been sympathetic to Russia for many decades,” Wright said. “That didn’t emerge in the middle of the campaign. That could be because he really believes it. It could be because he’s sought to do business in Russia for many decades, or it could be a mix of both.”
Trump’s view of how Russia works could also explain why, if he was keeping his business interests in mind, Trump thought it necessary to flatter Putin.
“Trump’s whole mind-set is, ‘I want to do a deal with the Russians. I want to work with the big guy and get the deal done,’” Wright said.
But Trump’s relentless praise of Putin during and since the campaign came after the autocrat had worked against U.S. interests in Europe and elsewhere, while stifling human rights at home.
“If you’re going to be leader of the free world, you’ve got to focus on being leader of the free world, not leader and businessman,” said Lanhee Chen, who was Republican nominee Mitt Romney’s top policy advisor during the 2012 presidential race and now is a research fellow at Stanford’s Hoover Institution.
Trump’s attempt to develop Trump Tower Moscow during the campaign “does cause you to wonder exactly what was going on,” he added.