Manafort took 18 trips to Moscow while working for Putin allies. | McClatchy Washington Bureau

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Political guru Paul Manafort took at least 18 trips to Moscow and was in frequent contact with Vladimir Putin’s allies for nearly a decade as a consultant in Russia and Ukraine for oligarchs and pro-Kremlin parties.

Even after the February 2014 fall of Ukraine’s pro-Moscow President Viktor Yanukovych, who won office with the help of a Manafort-engineered image makeover, the American consultant flew to Kiev another 19 times over the next 20 months while working for the smaller, pro-Russian Opposition Bloc party. Manafort went so far as to suggest the party take an anti-NATO stance, an Oppo Bloc architect has said. A key ally of that party leader, oligarch Viktor Medvedchuk, was identified by an earlier Ukrainian president as a former Russian intelligence agent, “100 percent.”

It was this background that Manafort brought to Donald Trump’s presidential campaign, which he joined in early 2016 and soon led. His web of connections to Russia-loyal potentates is now a focus of federal investigators.

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Manafort’s flight records in and out of Ukraine, which McClatchy obtained from a government source in Kiev, and interviews with more than a dozen people familiar with his activities, including current and former government officials, suggest the links between Trump’s former campaign manager and Russia sympathizers run deeper than previously thought.

What’s now known leads some Russia experts to suspect that the Kremlin’s emissaries at times turned Manafort into an asset acting on Russia’s behalf. “You can make a case that all along he ...was either working principally for Moscow, or he was trying to play both sides against each other just to maximize his profits,” said Daniel Fried, a former assistant secretary of state who communicated with Manafort during Yanukovych’s reign in President George W. Bush’s second term.

“He’s at best got a conflict of interest and at worst is really doing Putin’s bidding,” said Fried, now a fellow with the Atlantic Council.

A central question for Justice Department Special Prosecutor Robert Mueller and several congressional committees is whether Manafort, in trying to boost Trump’s underdog campaign, in any way collaborated with Russia's cyber meddling aimed at improving Trump’s electoral prospects.

His lucrative consulting relationships have already led a grand jury convened by Mueller to charge him and an associate with conspiracy, money laundering and other felonies – charges that legal experts say are likely meant to pressure them to cooperate with the wider probe into possible collusion.

Government investigators are examining information they’ve received regarding “talks between Russians about using Manafort as part of their broad influence operations during the elections,” a source familiar with the inquiry told McClatchy.

Suspicions about Manafort have been fueled by a former British spy’s opposition research on Trump. In a now-famous dossier, former MI6 officer Christopher Steele quoted an ethnic Russian close to Trump as saying that Manafort had managed “a well-developed conspiracy of cooperation” between the campaign and the Kremlin.

Jason Maloni, a spokesman for Manafort, called that allegation “false,” saying that Manafort “never – ever – worked for the Russian government.” He also denied that Manafort ever recommended Ukrainian opposition to NATO, saying he “was a strong advocate” of closer relations with the western military alliance while advising political parties there.

“Paul Manafort did not collude with the Russian government to undermine the 2016 election,” Maloni said. “No amount of wishing and hoping by his political opponents will make this spurious allegation true.”

Maloni declined to say whether, while in Moscow, Manafort met with any Russian government officials.

Land of the oligarchs

The trail of Manafort’s decade of dealings 5,000 miles from America’s capital is murky. But the previously unreported flight records, spanning from late 2004 through 2015, reflect a man seemingly always on the move. Over those years, Manafort visited Ukraine at least 138 times. His trips between Ukraine and Moscow all occurred between 2005 and 2011 and were mostly in 2005 and 2006.

Prosecutors have charged that Manafort and associate Rick Gates funneled through a maze of foreign accounts at least $75 million in consulting fees from an array of Kremlin-leaning clients: Russian billionaire Oleg Deripaska, who secretly paid them $10 million annually for several years; a second Ukrainian oligarch; and the ruling Party of Regions, which supported Yanukovych until corruption allegations and bloody protests led to his overthrow in February 2014.

Maloni said Manafort’s trips to Russia were “related to his work on behalf of Oleg Deripaska’s commercial interests.”

The further unmasking of Manafort’s relationship with Deripaska in recent months, however, has heightened suspicions about Manafort.

In July 2016, weeks after he was named Trump’s campaign chairman, Manafort crafted an unusual, eyebrow-raising proposal for Deripaska, a member of Putin’s inner circle. In emails first reported by the Washington Post, Manafort offered in seemingly coded language to provide “private briefings” on the U.S. presidential race for the Russian aluminum magnate. Manafort directed a trusted associate, Konstantin Kilimnik, to relay his message to Deripaska, remarking that it could be a way to make himself “whole” — possibly an allusion to a multimillion-dollar legal action Deripaska had filed against Manafort. Kilimnik, a Ukrainian citizen, once attended a Russian military academy known for training spies.

Deripaska, who did not respond to a request for comment, has denied seeing Manafort’s proposal and says it went nowhere. Kilimnik did not respond to emailed questions, but he has denied in published reports having any connection to Russian intelligence services.

California Rep. Adam Schiff, the lead Democrat in the House Intelligence Committee’s inquiry, told McClatchy: “It certainly looks like Mr. Manafort viewed his position on the campaign as a way of further profiting personally from the work that he was doing on behalf of Russian interests.”

Manafort’s proposal to Deripaska “shows a certain willingness to trade information in the hope of obtaining financial rewards from pro-Russian interests,” Schiff said in a phone interview. “If accurate, that’s a dangerous quality to have in a campaign chairman for a presidential campaign.”

Two former U.S. government officials with knowledge of the way Putin operates said three of the oligarchs with whom Manafort had contacts – Deripaska, Dmitry Firtash, who helped finance the party behind Yanukovych, and Medvedchuk – were potential conduits with the Kremlin.

“All three of those guys are able to pass messages directly to Putin, as well as to his subordinates and aides within the Russian presidential administration,” said one of the ex-officials, who spoke on condition of anonymity because of the sensitivity of the matter. “So they all have access and Manafort knew all three or their close associates fairly well.”

No evidence has surfaced that Manafort used any of them to pass messages between the campaign and the Kremlin.

During Manafort’s five-month tenure with the campaign, Russian emissaries made at least two behind-the-scenes offers to deliver “dirt” about Clinton to Trump’s campaign, including at a June 9, 2016 meeting in Trump Tower three weeks after Manafort was promoted to campaign chairman; he attended the meeting along with Donald Trump Jr., Trump son-in-law Jared Kushner and a Russian lawyer. Trump’s aides say nothing came of that discussion, or a similar offer conveyed in April 2016 to foreign policy adviser George Papadopoulos; Manafort was copied on an email relaying that offer, which said the Russians had “thousands” of emails from Democrats.

In July, days before the Democratic National Convention, the British transparency group WikiLeaks began publishing thousands of embarrassing emails stolen from the Democratic National Committee. U.S. intelligence agencies have concluded that Russia was behind the hacking, and also was responsible for the social media dissemination of a blizzard of fake and harshly critical news about Trump’s opponent, Hillary Clinton.

Schiff, emphasizing he could only discuss what’s on the public record, said “these are some of the communications and interactions that are of deep interest to us, because obviously the timing is highly suggestive. It’s one of the reasons why Manafort is such a key figure in all of this.”

Globe-trotting consultant

Manafort first began to establish connections in Ukraine – ground zero in the geopolitical struggle between Putin’s Russia and the West – in late 2004. His reputation as a masterful political strategist and fixer was earned over decades hopping planes to the Congo, Philippines and elsewhere to advise authoritarian rulers friendly with the United States.

By the end of that year, the former Soviet republic of Ukraine was paralyzed by widespread protests amid allegations that Yanukovych, the prime minister in a government rife with corruption, had won the presidency in a rigged election. What became the Orange Revolution persisted until another, internationally monitored vote was held and rival Victor Yushchenko was declared the winner.

Manafort and a partner formed Davis Manafort Partners Inc. in early 2005 and opened offices in Kiev.

Manafort’s first client in Ukraine was Rinat Akhmetov, the country’s richest man and a key funder of Yanukovych’s Party of Regions. Deripaska introduced Manafort to Akhmetov, who hailed from Russia-leaning Eastern Ukraine. In the summer of 2005, Akhmetov tapped Manafort to help Yanukovych and his party in the 2006 elections, according to an American consultant based in Kiev, who spoke on condition of anonymity to avoid damaging relationships.

The multimillion-dollar political consulting deal was sealed at a meeting in an elite Moscow hotel attended by Manafort, Akhmetov and a half dozen other wealthy Ukrainians.

Manafort spent the next several years advising Deripaska, Akhmetov and other Ukrainian oligarchs and giving the gruff-talking Yanukovych a makeover down to his hair style and attire. Yanukovych won the presidency in 2010.

In 2014, however, Manafort’s business took a hit when Yanukovych fled to Russia, days before Kremlin-backed forces invaded Eastern Ukraine. He was quickly hired by the Opposition Bloc, which leaned even more toward Moscow.

His work drew rave reviews from one Oppo Bloc leader, Nestor Shufrych, whom multiple people in positions to know described as a close ally of Medvedchuk. Shufrych told a Ukrainian publication that Manafort urged the new party to take an anti-NATO stance and be the “voice of Russians in (Ukraine’s) East.”

Calling Manafort “a genius,” Shufrych said the party had paid him about $1 million, and the investment “paid off.”

Philip Griffin, a former associate of Manafort’s who consults in Kiev, said he could not imagine Manafort opposing NATO. “Paul Manafort is a Reagan Republican,” Griffin said. “He would never betray that legacy by doing Russia’s bidding.”

Maloni said Manafort argued strongly that “Ukraine was better served by having closer relations with the West and NATO.”

He also said Manafort succeeded in pushing “a number of major initiatives that were strongly supported by the U.S. government and opposed by Russia,” including the denuclearization of Ukraine and the expansion of NATO exercises in the region.

Some former U.S. government officials, though, are skeptical.

Despite Ukraine’s popular uprising against Yanukovych that led to at least 75 deaths, “Paul Manafort maintained ties to the Opposition Bloc party and Viktor Yanukovych's former cronies, thus choosing to associate himself with crooks and kleptocrats rather than Ukraine's pro-Western reformers,” said Mike Carpenter, who focused on Russia matters as a top Pentagon and National Security Council official during the Obama administration. “This speaks volumes about his character and lack of respect for democratic values.”

One of Shufrych’s and Oppo Bloc’s behind-the-scenes allies was Medvedchuk, who is so close to Putin that the Russian president is the godfather of his daughter.

Partial transcripts from tape recordings of then-Ukrainian president Leonid Kuchma, published in 2002, show Kumcha saying: “Well, we know about it, that he was a KGB agent, 100 percent.”

Details of Manafort’s contacts with Medvedchuk could not be learned. But Medvedchuk, who is under U.S. sanctions, has acknowledged meeting Manafort once in 2014.

Flights of interest

Several of the trips in Manafort’s flight records could draw investigators’ interest.

In April 2014, for instance, Manafort traveled to Vienna. Ukrainian oligarch Firtash had been arrested there the prior month on U.S. charges that he helped orchestrate an $18.5 million bribery scheme involving the government of India, a U.S. firm and a Firtash company in the Virgin Islands. A former U.S. government official, who declined to be identified because of the sensitivity of the matter, said Manafort met with Firtash in Vienna, where he is awaiting extradition to the United States.

Another Manafort trip that could interest investigators took place in July 2013 when Manafort and Kilimnik flew from eastern Ukraine to Frankfurt on a private plane owned by Belbek Avia, according to the flight records. The aircraft company's founders included the father of Andrey Artemenko, a Ukrainian legislator. Through an attorney, Andrey Artemenko denied that Belbek Avia ever owned an aircraft.

American experts on Russia said privately they suspect the trip was a prelude to a broader Russian influence effort to dissuade Yanukovych’s government from signing an agreement to associate with the European Union. That decision, experts say, opened the door to Russia’s 2014 invasion of eastern Ukraine. This year, Artemenko was expelled from the Ukrainian legislature and his citizenship was revoked after disclosures he and a Trump attorney had pitched a “peace plan” for Ukraine and Russia widely seen as favoring Moscow.

Pro-Russia stances

Some of Trump’s most remarked-upon statements about foreign policy that directly or indirectly implicated Russia occurred on Manafort’s watch in the 2016 campaign. For example, Trump launched broadsides against NATO allies for not contributing enough money and suggested the United States might rethink its commitment to the European mutual defense alliance credited with deterring Russian military ambitions.

Trump also raised doubts about whether he would stand behind U.S. sanctions that President Barack Obama imposed in December 2014 in retaliation for the Crimean invasion.

As the GOP platform committee drew up party positions a week before the Republican National Convention, a plank calling for the United States to provide “lethal weapons” for Ukraine’s defense was altered in a controversial and mysterious move. The American consultant in Ukraine said that Manafort aide Kilimnik had boasted he played a role in easing the language to recommend only “appropriate assistance” to Ukraine’s military.

Charlie Black, a onetime partner of Manafort’s, says he remains baffled by the change.

"It was inexplicable to me that a majority of platform members would have taken a pro-Russian position on Ukraine,” he said. “They must not have known this was a pro-Russia provision.”

In late July after FBI Director James Comey said he would not back prosecution of Clinton over her use of a private email server to conduct State Department business, Trump took a bizarre step. He publicly beseeched Russia to help unearth 30,000 emails that Clinton said she had deleted because they dealt with personal matters.

During the summer, a U.S. group supporting Ukraine asked both presidential candidates for a letter recognizing the country’s 25th year of independence since the fall of the Soviet Union. Clinton obliged. But the Ukrainian Congress Committee of America was unable to wrest a letter from the Trump campaign, said a person familiar with the matter. The group’s president did not respond to phone messages.

Manafort resigned from the campaign on Aug. 19, 2016 after The New York Times disclosed a secret Ukrainian ledger indicating he was to receive more than $12 million in off-the-books payments from Yanukovych’s party from 2007 to 2012.

Schiff said he found an intriguing symmetry between Trump’s Russia stances and Manafort’s work in Kiev that might explain their mutual attraction.

“Whether he was attracted to the Trump campaign or the campaign was attracted to him on the basis of his Russian contacts,” Schiff said, “the fact of the matter is, he did bring those Russian contacts and pro-Russian prejudices with him to the campaign and apparently found a welcome home there.”

Correction and clarification: The story has been updated to say that the aircraft used on one flight was not owned by Andrey Artemenko, but rather by an aircraft company whose founders included his father; and to include that Artemenko denies that the company ever owned an aircraft or that he has ever been "pro-Russian."

Kevin G. Hall, James Whitlow and the Organized Crime and Corruption Reporting Project contributed to this story. Peter Stone is a McClatchy special correspondent.

This story was originally published November 27, 2017 5:00 AM.