Dozens of interviews, court filings and other documents show Mr. Kilimnik to be an operator who moved easily between Russian, Ukrainian and American patrons, playing one off the other while leaving a jumble of conflicting suspicions in his wake. The effort to disentangle the mysteries surrounding him seems likely to leave questions even after the conclusion of the special counsel’s work.
To American diplomats in Washington and Kiev, he has been a well-known character for nearly a decade, developing a reputation as a broker of valuable information like the alliances of Ukraine’s oligarchs and the country’s handling of foreign investment and sensitive criminal cases.
.. Prosecutors have also scrutinized the effort by Mr. Manafort and Mr. Kilimnik to drum up political consulting business with Kremlin-aligned political figures in Ukraine and Russia who were pushing plans to end the simmering conflict between the countries.
Those so-called peace plans could have resulted in the easing of sanctions imposed on Russia by the United States — a policy shift to which Mr. Trump had signaled an openness during the campaign and one that would have been a major foreign policy victory for the Kremlin.
.. To some of those he encountered, he was an impish, 5-foot-tall cynic whose American associates nicknamed him “Carry-on” or “KK” and who was rejected for a job with an oil company in Moscow in late 2003 or early 2004 because he was seen as too meek.
At the same time, he did little to defuse long-running suspicions that he was a Russian agent. And his involvement in discussions related to back-channel peace negotiations between Ukraine and Russia attracted attention from President Barack Obama’s National Security Council, which saw him as a functionary for oligarchs working to sell out Ukraine to Moscow’s benefit, a former United States official said.
Mr. Kilimnik, 49, who has Russian citizenship, now lives in Moscow. He is unlikely to ever face obstruction of justice charges that the special counsel brought against him and Mr. Manafort. And the once chatty operative — who was known for kibitzing with reporters, diplomats and political consultants over WhatsApp and in the bar of the Hyatt hotel in Kiev — has gone dark.
Mr. Kilimnik quickly made himself indispensable to Mr. Manafort, who spoke neither Ukrainian nor Russian. At the time, Mr. Manafort worked as a political and business consultant to the Ukrainian steel and coal oligarch Rinat L. Akhmetov, as well as the Russian aluminum oligarch Oleg V. Deripaska.
Mr. Kilimnik traveled extensively with Mr. Manafort, accompanying him to all his meetings and eventually becoming known as “Manafort’s Manafort” in Kiev.
“Paul took Konstantin under his wing, not just as a protégé but as his own surrogate son,” Mr. Caputo said.
Mr. Gates, who joined Mr. Manafort’s Ukraine team the year after Mr. Kilimnik and has since pleaded guilty to charges brought by Mr. Mueller stemming from his work there, later told an associate he knew that Mr. Kilimnik was a former officer with the G.R.U., according to a court filing by Mr. Mueller’s team.
In a February 2017 interview with The New York Times in Kiev, Mr. Kilimnik denied ever serving in a Russian intelligence agency. “What would I do if I were a real Russian spy?” he said. “I would not be here. I would be in Russia.”
But for the politicians and oligarchs who were Mr. Manafort’s clients, Mr. Kilimnik’s suspected intelligence connections suggested a seal of approval from Moscow. That was an important selling point, especially when combined with Mr. Manafort’s connections. The perception in political circles in Kiev was that hiring Mr. Manafort’s team would open doors in Washington and Moscow.
Mr. Akhmetov persuaded Mr. Manafort to try to resuscitate the political career of the former Ukrainian prime minister Viktor F. Yanukovych, a Russia-aligned figure who lost the 2004 presidential election amid allegations of vote-rigging.
In Mr. Yanukovych’s Party of Regions, Mr. Kilimnik was “known as the representative of Russia,” said Taras V. Chernovyl, a former party member.
With help from Mr. Manafort and Mr. Kilimnik, Mr. Yanukovych won the presidency in 2010.
Mr. Manafort, who was not known for spreading the wealth among his subordinates, paid Mr. Kilimnik $530,000 for “professional services and administrative overhead for Kiev operations” from June 2013 to January 2014, according to Justice Department lobbying filings, which show that Mr. Manafort’s company was paid $17 million over a two-year stretch around that time.
.. By then, Mr. Kilimnik was married with two children. His family lived in a modest house not far from Sheremetyevo International Airport in Moscow, where he traveled most weekends. But he lived a parallel life in Kiev, where he embraced trappings of his boss’s jet-setting lifestyle, trading the khakis and sweaters he wore at I.R.I. for tailored suits, a chauffeur-driven German car and evenings at an estate with a pool.
Things started going south for Mr. Yanukovych and, by extension, Mr. Manafort and Mr. Kilimnik, in late 2013, as mass protests erupted over the government’s corruption and pivot toward Russia. Mr. Yanukovych stepped down and fled in February 2014, eventually arriving in Moscow.
Russia began a military incursion into eastern Ukraine in 2014. And Mr. Kilimnik leveraged his access to American diplomats for a new endeavor.
He turned up in Donetsk as the city was slipping into war, presenting himself as having “the State Department’s ear, the American ear in general,” said Aleksei Kovzhun, a member of a group of pro-Ukrainian political advisers working there.
.. Mr. Kilimnik joined their ranks, and in emails reviewed by The Times, he encouraged them to appease the Russian-speaking population, who, he wrote, merely wanted “stable work, good salaries and a turn to the better for their children.”
The American Embassy was overly focused on the Russian military threat, he said. “The whole American Embassy is counting barricades,” he wrote, adding about the United States diplomats he was in contact with, “the idiots.”
In hindsight, Mr. Kovzhun said, “I can see that he could easily be a Russian agent who just came to monitor the situation, and be in the center of pro-Ukrainian power in the region.”
With their primary benefactor in exile, Mr. Manafort and Mr. Kilimnik sought business with Russia-aligned factions that arose from the ashes of Mr. Yanukovych’s party.
A common goal for these factions was to pursue initiatives to settle the Ukraine conflict on terms seen by many in the country as favorable to Russia, and as an opening for an effort to persuade the United States and its allies to lift sanctions on Moscow.
Among the Russia-aligned Ukrainians they advised was Oleksandr V. Klymenko, who was a minister in Mr. Yanukovych’s government. Mr. Manafort and Mr. Kilimnik discussed plans to conduct polling in connection with a possible bid by Mr. Klymenko for president of Ukraine in 2019, even though he was living in exile in Moscow and under European Union sanctions, according to three people briefed on their activities.
Another client was a party backed by Serhiy Lyovochkin, a television company owner who served as Mr. Yanukovych’s chief of staff. The party, known as Opposition Bloc, had fallen behind in paying Mr. Manafort’s invoices, according to Mr. Kilimnik and other people familiar with the situation, and the pair hoped to persuade Mr. Lyovochkin to turn the spigot back on.
.. The situation was on Mr. Kilimnik’s agenda when he headed to the United States within a month of Mr. Manafort’s joining the Trump campaign, telling associates in Kiev that he also hoped to meet with Mr. Trump and to potentially work with his campaign in some capacity.
A White House spokesman said Mr. Trump was introduced to thousands of people during the 2016 campaign. While it is possible he met with Mr. Kilimnik, “the president has no recollection of it,” the spokesman said.
Around the time of Mr. Kilimnik’s trip to the United States in spring 2016, Mr. Manafort directed Mr. Gates to transfer some polling data to Mr. Kilimnik, including public polling and some developed by a private polling company working for the campaign, according to a person with knowledge of the arrangement.
Mr. Manafort asked Mr. Gates to tell Mr. Kilimnik to pass the data to Mr. Lyovochkin and Mr. Akhmetov, the person said. Representatives for both Mr. Lyovochkin and Mr. Akhmetov said they neither requested nor received the data, and would have had no use for it.
Mr. Mueller’s team has focused on what appears to have been another discussion about polling data in New York on Aug. 2, 2016. A partly redacted court transcript suggests that Mr. Gates, who entered a plea agreement with the special counsel that requires his cooperation, may have told prosecutors that Mr. Manafort had walked Mr. Kilimnik through detailed polling data at a meeting that day in the cigar lounge of the Grand Havana Room in Manhattan.
.. The meeting also included a conversation about one Ukrainian “peace plan,” according to court filings.
Prosecutors contend that Mr. Manafort lied to them about the meeting and other interactions with Mr. Kilimnik. Those lies, a federal judge ruled, violated Mr. Manafort’s agreement to cooperate with prosecutors in exchange for consideration of a reduced sentence related to his work in Ukraine.
Mr. Manafort’s lies about his interactions with Mr. Kilimnik gave “rise to legitimate questions about where his loyalties lie,” Judge Amy Berman Jackson said.
.. Just before Mr. Manafort was forced to resign from the Trump campaign in mid-August 2016 amid scrutiny of his work in Ukraine, the F.B.I. opened an investigation into the campaign’s possible ties to Russia.
It led to a guilty plea by Mr. Trump’s first national security adviser, Michael T. Flynn, for lying to the F.B.I. about conversations with the Russian ambassador related to the sanctions.
By the inauguration, investigators were focusing on Mr. Kilimnik and his connections to Mr. Manafort.
Yet Mr. Kilimnik again traveled to the United States for Mr. Trump’s inauguration, meeting in the Washington area with Mr. Manafort, according to Mr. Mueller’s team.
.. While the trip was not publicly revealed until nearly two years later, it was on the F.B.I.’s radar. Peter Strzok, the agent who oversaw the bureau’s investigation of Russian interference in the election until he was reassigned and later fired for sending text messages critical of Mr. Trump, expressed frustration when he learned that Mr. Kilimnik had come and gone without being interviewed by agents.
Yet Mr. Kilimnik again traveled to the United States for Mr. Trump’s inauguration, meeting in the Washington area with Mr. Manafort, according to Mr. Mueller’s team.
While the trip was not publicly revealed until nearly two years later, it was on the F.B.I.’s radar. Peter Strzok, the agent who oversaw the bureau’s investigation of Russian interference in the election until he was reassigned and later fired for sending text messages critical of Mr. Trump, expressed frustration when he learned that Mr. Kilimnik had come and gone without being interviewed by agents.
“Everything is completely falling off the rails,” Mr. Strzok wrote in a text to a colleague on Jan. 23, 2017 — three days after the inauguration — referring to the missed opportunity.
The month after the inauguration, Mr. Kilimnik and Mr. Manafort met again and discussed a poll being planned for Mr. Klymenko’s prospective presidential campaign, according to court filings and interviews.
The poll was not conducted, according to people familiar with the arrangement, and Mr. Klymenko ultimately did not run.
In previously unpublished messages to The Times around the time of that meeting, Mr. Kilimnik suggested that the escalating news coverage was making him a target in both Ukraine and Russia.
“After another surge of attention, I am sure I will finally get on the radar screen of the Russian authorities,” he wrote.
Mr. Manafort’s allies point out that Mr. Mueller’s team has not publicly presented any evidence that Mr. Kilimnik is a Russian agent. They argue that it is unlikely that he is an agent because he was able to travel freely to the United States and deal regularly with its officials. To buttress this case, Mr. Manafort’s lawyers requested and received records from the government showing that Mr. Kilimnik communicated with officials at the American Embassy in Kiev.
“If he was a Russian intelligence asset, then the State Department officials who met with him over the years should be under investigation,” Mr. Caputo said.
“Watch for the defense to become the thing they’ve denied, because the truth is worse,” said Wallace, noting that originally, the Trump team tried to flat-out deny there was any collusion with Russia. “They’re not even denying, because they’ve pleaded guilty to these contacts with Russians … this is a campaign whose defense to collusion is, ‘we couldn’t collude with our press office.’ That’s what Brad Pascale and Jared Kushner say.”
.. “They could collude, they were colluding, and all of this is so nefarious,” said Kirschner. “It’s not reckless, it’s not happenstance, it’s not careless … what I found remarkable in what [special counsel prosecutor] Andrew Weissman was saying to the court, when they were trying to decide whether Paul Manafort’s plea agreement should basically be torn up because he lied. As a cooperating witness, he kept lying to the special counsel.”
.. What I find remarkable is that Manafort gets charged, right, federally indicted. What does he do after that? He starts tampering with witnesses. And he was charged for tampering with witnesses. After that we have now learned through this litigation, albeit in highly redacted form, that he continued to conspire with [suspected Russian agent Konstantin] Kilimnik.”
“What is it that they so desperately want to cover up?” said Kirschner. The answer, he said, was in the fact that Weissman told the judge that the Kilimnik interactions go “right to the heart of what the special counsel is investigating.”
Rachel Maddow reports on an avalanche of legal news including details in the Paul Manafort case exposed by a lawyer’s poor redactions, an intriguing new indictment, and another development in the mystery Mueller case.
Investigators alleged that Mr. Manafort made inaccurate statements in interviews with Mr. Mueller’s team about his communications with Konstantin Kilimnik, said the people familiar with the matter.
.. Mr. Kilimnik, who Mr. Mueller charged earlier this year along with Mr. Manafort with trying to influence the testimony of two witnesses against Mr. Manafort, had worked for Mr. Manafort’s lobbying firm in Ukraine. Messrs. Manafort and Kilimnik communicated earlier this year about contacting others who worked with them in an alleged effort to coordinate their stories
.. Mr. Mueller has long been interested in the relationship between Messrs. Manafort and Kilimnik.
.. He has questioned witnesses about a boat trip that Mr. Manafort took with Tom Barrack, a longtime friend of Mr. Trump, after Mr. Manafort was ousted from the Trump campaign in August 2016, say people familiar with the matter. Witnesses believed investigators were seeking to determine whether Mr. Manafort ever met with Mr. Kilimnik on that trip.
.. With the Mueller-Manafort dispute breaking into public view, some legal experts believe Mr. Manafort’s best hope for leniency is to obtain a presidential pardon. On Wednesday Mr. Trump told the New York Post a pardon for Mr. Manafort was “not off the table.” Any pardon would likely spark a firestorm among Democrats, who are preparing to take control of the House.
.. Senate Republicans Wednesday blocked an effort to pass legislation protecting Mr. Mueller’s investigation.
For the second time this month, Sens. Jeff Flake (R., Ariz) and Chris Coons (D., Del.) tried to pass by unanimous consent legislation designed to protect Mr. Mueller from being fired. They were blocked by Sen. Mike Lee (R., Utah) on Wednesday. Two weeks earlier, Senate Majority Leader Mitch McConnell (R., Ky.) had objected, blocking the bill.
testified that he knew about what the prosecutors allege is a multiyear tax and bank fraud scheme by Mr. Manafort because “I was the one who helped organize the paperwork.”
.. Mr. Manafort’s allies argue that Mr. Gates can be discredited as a morally bankrupt and untrustworthy narrator who owes his professional career to Mr. Manafort, yet siphoned millions from his accounts. Then, faced with the prospect of prison and huge fines, Mr. Manafort’s allies say, he blamed Mr. Manafort for financial machinations that he himself executed. The defense also signaled Monday that it may allege extramarital affairs by Mr. Gates in a further attempt to attack a man who Mr. Manafort’s friends say took advantage of his boss.
.. “Rick Gates owes everything to Paul. Paul made Rick a lot of money,” said Hector Hoyos, a longtime friend and former business partner of Mr. Manafort’s who remained in contact with him after his indictment. “But Rick is not the strong-valued guy that Paul is. Rick will go wherever the wind takes him, and it just goes to show you that there is no such thing as loyalty and friendship anymore,” Mr. Hoyos said in June
.. The men spent countless hours together traveling the world, and by all accounts got along quite well. But in some ways they are a study in contrasts. Prosecutors have detailed the lavish lifestyle on which Mr. Manafort spent his riches, while Mr. Gates, by contrast, lived less ostentatiously. When he wore a suit, he still carried a backpack.
.. Even as he detailed Mr. Manafort’s financial crimes, Mr. Gates worked in a bit of praise for his former boss.
“Probably one of the most politically brilliant strategists I’ve ever worked with,” he said of Mr. Manafort.
.. While Mr. Gates was the one who demanded accountants give him copies of financial statements in PDF format so he could convert them to Word and alter them, some of the falsified documents bear Mr. Manafort’s signature.
.. Mr. Manafort told the accountants that he had no foreign bank accounts, although prosecutors claim that millions of dollars flowed through his accounts in Cyprus and St. Vincent and the Grenadines
.. Judge T.S. Ellis III of the United States District Court in Alexandria said prosecutors had proved both that Mr. Manafort personally denied that those accounts existed and that he controlled them.
.. Mr. Manafort left the firm the year Mr. Gates arrived. But they continued traveling in the same circles as Mr. Gates impressed remaining partners, whom he occasionally chauffeured between the firm’s Alexandria offices and meetings in Washington.
“Very smart. Good work ethic. He was a guy I thought would go places someday,” said Charlie Black, a co-founder of the firm, who offered Mr. Gates the internship at the recommendation of a friend, and then hired him full-time afterward. “I didn’t know where he would end up, but I always liked him. I still do.”
.. The accountant, Cynthia Laporta, testified that in 2006, Mr. Manafort received a $10 million loan from Oleg V. Deripaska, a Russian oligarch close to President Vladimir V. Putin. Ms. Laporta said she saw no evidence it was ever repaid.
And Mr. Gates testified that Konstantin V. Kilimnik, a Russian who prosecutors claim is tied to Russian intelligence, had signatory authority over some of Mr. Manafort’s accounts in Cyprus.
.. there were 82 known “contacts between the Trump team and Russia-linked operatives.”
.. the June 9, 2016, meeting at Trump Tower between the Trump campaign high command and Kremlin emissaries promising dirt on Hillary Clinton as part of the Kremlin’s “support for Mr. Trump.” “If it’s what you say, I love it,” Donald Trump Jr. gushed. When this was revealed last summer, President Trump personally orchestrated an attempted coverup by claiming the meeting was about adoptions.
This was shortly after Trump fired FBI Director James B. Comey to stop the investigation of “this Russia thing,” as he put it in an interview with “NBC Nightly News” — showing just how much he fears this inquiry.
.. Trump’s deputy campaign manager, Rick Gates, was in touch in 2016 with Konstantin Kilimnik, a business associate with “ties to Russian intelligence.” Campaign chairman
Paul Manafort, who has a long history of representing Russian interests and was running the campaign for no pay, also reportedly met with Kilimnik in 2016.
Manafort was also in contact with the Russian oligarch Oleg Deripaska (whom he owed at least $10 million) , offering him “private briefings” that would no doubt have been instantly conveyed to Putin.
.. Russians first tried to hack into Clinton’s email on July 27, 2016, hours after Trump asked them to do just that (“Russia, if you’re listening”).
.. Both Stone and Donald Trump Jr. were also in contact with WikiLeaks, the Russians’ conduit for releasing stolen emails. Surely it is no mere coincidence that Stone predicted on Aug. 21, 2016 — nearly seven weeks before Clinton campaign chairman John Podesta’s stolen emails were released — that “it will soon [be] Podesta’s time in the barrel.”
.. the indictment also reveals that the Russians stole not just emails but also the data analytics Democrats used to run their campaign. This happened in September 2016. A few weeks later, the Trump campaign shifted its “datadriven” strategy to focus on the states that would provide the margin of victory, raising the question of whether it benefited from stolen Democratic data.
.. The application, approved by four Republican judges, notes that “the FBI believes that the Russian Government’s efforts are being coordinated with Page and perhaps other individuals associated with Candidate #1’s [Trump’s] campaign.” It also says that Putin aide Igor Diveykin “had met secretly with Page and that their agenda for the meeting included Diveykin raising
a dossier or ‘kompromat’ that the Kremlin possessed on Candidate #2 [Clinton] and the possibility of it being released to Candidate #1’s campaign.”
.. Helsinki, where Trump refused to criticize Putin and insisted on meeting with him alone for two hours. Why doesn’t Trump want his own aides in the room when he talks with Putin? What does he have to hide?
.. Former director of national intelligence James R. Clapper Jr. , among others, suspects that Putin has “something” on Trump — perhaps evidence of financial wrongdoing. But, by now, any such “kompromat” could well include the help that Russia provided in 2016. Trump certainly gives the impression that he knows how much he owes Russia and how important it is to repay that debt lest Putin release the evidence that might bring him down. And the
Putin Republicans give the impression that they couldn’t care less if the president plotted to win power with help from a hostile foreign state.
Roger Stone, means that at least six members of Trump’s broader team knew about offers of dirt from Russians during that campaign — and, depending on how that information was shared, as many as 10 may have, including Trump.
.. Papadopoulos sent an email to Trump adviser Stephen Miller the day after Mifsud reached out to him, telling Miller he had some “interesting messages” coming in from Moscow.
.. Trump’s argument has long been that there was no collusion between his campaign and the Russian government. That claim increasingly depends on how one defines “collusion.”