FILE - A man walks along Red Square, with the mausoleum of Soviet state founder Vladimir Lenin, right, and St. Basil's Cathedral seen in the background, in central Moscow, Russia, Dec. 21, 2015.
FILE - A man walks along Red Square, with the mausoleum of Soviet state founder Vladimir Lenin, right, and St. Basil's Cathedral seen in the background, in central Moscow, Russia, Dec. 21, 2015.

WASHINGTON - As the controversy over Russian hacking during the presidential election intensified in the lead up to President Donald Trump’s January 20 inauguration, Trump took to Twitter to push back at critics of his campaign’s alleged overtures to Russia.

“Russia has never tried to use leverage over me,” Trump tweeted January 11. “I HAVE NOTHING TO DO WITH RUSSIA -- NO DEALS, NO LOANS, NO NOTHING!” he wrote.

In fact, Trump has doggedly pursued business deals in Russia, going back decades to the twilight of the Soviet Union.

As a rising New York real estate tycoon with presidential ambitions in the 1980s, Trump developed a keen interest in foreign policy issues, including nuclear disarmament.

A supporter of former President Ronald Reagan, he advocated for nuclear disarmament negotiations with the Soviet Union, but the Reagan White House showed no interest in his offer to lead the talks.

FILE - U.S. President Ronald Reagan (R) and Soviet
FILE - U.S. President Ronald Reagan (R) and Soviet President Mikhail Gorbachev sign the Intermediate-Range Nuclear Forces (INF) treaty at the White House in Washington, Dec. 8, 1987.

Height of Cold War

It was the height of the Cold War, and in nuclear disarmament talks Trump saw an opportunity to leave a mark on one of the most pressing issues of the day and along the way raise his public profile, experts said.

“I don’t think it’s a stretch to say that Trump saw an opportunity to involve himself in an important area at the moment,” said Zachary Witlin, a Russia expert at the Eurasia Group in New York.

With former Soviet leader Mikhail Gorbachev leading a program of political and economic reforms known as “perestroika” in 1980s, Trump saw an opening for investment in the Soviet Union.

In 1987, he met with Gorbachev in Washington and later reported that they “got along well” despite their “very different” philosophies.

FILE - A doorman stands as people walk past the Tr
FILE - A doorman stands as people walk past the Trump Tower in New York, May 23, 2016.

A 1986 meeting with Soviet ambassador Yuri Dubinin at Trump Tower led to an all-expenses paid trip the following year to Leningrad and Moscow, where Trump met with tourism officials to discuss building luxury hotels. Though nothing came out of the trip, Trump later praised Gorbachev for “opening up the country.”

“As a shrewd businessman, he saw an untapped market in the Soviet Union,” said Boris Zilberman, a Russia expert at the Foundation for the Defense of Democracies in Washington. “He was looking for an opportunity to capitalize on, but it never materialized.”

Dissolution of Soviet Union

But other opportunities would soon appear on the horizon as the dissolution of the Soviet Union in 1991 ushered in a wave of privatization of lucrative state-owned assets under former President Boris Yeltsin. Western investors flocked in for a piece of the action. Trump got on the bandwagon, albeit tentatively, and some say too late.

Indeed, it wasn't until 1996 that Trump made his second trip to Moscow, carrying a proposal to build a luxury complex on property owned by U.S. tobacco company Liggett-Ducat. He praised the city’s development potential and trademarked his brand in keeping with a practice of registering his name in anticipation of developing a project.

At least seven other trademark registrations followed over the next decade, but none led to an actual development.

Why Trump, the consummate dealmaker who survived multiple bankruptcies and built a global brand, failed to secure any major deals in Russia remains a mystery.

One explanation is Trump grew increasingly leery of doing deals in Russia as organized crime flourished, oligarchs seized power and the business environment increasingly appeared unregulated. Indeed, in 1999, he pronounced Russia a country “out of control” and described its ailing leader as “a disaster.”

But Witlin, of the Eurasia Group, offers another reason: Trump’s lack of well-connected local partners.

“In the 1990s and even today, in order to navigate in Russia, it helps a lot to have a local partner who understands the local market, knows the rules of the game, and knows the actors,” Witlin said. “He just didn’t have the connections.”

FILE - Miss Universe 2013 Gabriela Isler, Donald T
FILE - Miss Universe 2013 Gabriela Isler, Donald Trump, co-owner of the Miss Universe Organization, and businessman Aras Agalarov take part in a news conference after the Miss Universe pageant at the Crocus City Hall in Moscow Nov. 9, 2013.

But when Trump found the right partner, success found him quickly. Case in point: Aras Agalarov, an Azerbaijan-born billionaire real estate developer with close ties to Russian President Vladimir Putin.

In 2013, Trump, then a co-owner of the Miss Universe beauty pageant, signed a $20 million deal with Agalarov to host the pageant in his Crocus concert hall in Moscow.

To bring Miss Universe to Moscow, Trump “had the right partner,” Witlin said.

Tentative deal

The splashy event put Trump on Russian television. Though Putin did not show for the pageant despite Trump's Twitter enticements, Trump later claimed that he'd met all the oligarchs in Russia and tweeted: "TRUMP TOWER-MOSCOW is next."

Despite his failure to build a hotel in Russia or to license his name to Russian property developers, however, Trump had far greater success in getting Russian investors, large and small, to invest in his developments in the U.S.

In 2006, he partnered with Bayrock Group, a New York-based real estate company founded by Soviet emigres, to develop the $450 million Trump Soho hotel condominium project. All the while, Russian investors, looking for safe investment opportunities, began snapping up Trump condos in New York and Florida.

While describing Russia as a difficult business environment, Trump’s son Donald Jr. touted Russian investment thirst for Trump properties.

“Russians make up a pretty disproportionate cross section of a lot of our assets,” Donald Trump Jr. told a real estate conference in 2008. “We see a lot of money pouring in from Russia.”

FILE - Donald Trump talks to his sons Donald Trump
FILE - Donald Trump talks to his sons Donald Trump, Jr., and Eric Trump after the second presidential debate, Oct. 9, 2016.

To insulate himself against conflicts of interest while in office, President Trump recently handed control of his business empire to sons Donald Trump Jr. and Eric Trump. Under an arrangement announced before inauguration, he also vowed that his company would be making no deals while he’s in the White House.

Nevertheless, experts say conflicts of interest, whether perceived or real, will continue to dog the new president, even though he has no business interest in Russia.

“I think given the extent to which that idea has been so discussed, popularized and has become an issue of concern for a large swath of the public, it would be difficult to shake off that impression no matter what happens there,” Witlin said.