Paul Manafort spent decades pushing the envelope of what’s legal. His trial strategy is just as high-risk.

“Paul is an envelope expert: he knows exactly where the edge of it is.”

Paul Manafort was heading to jail, and the judge had a few choice words for him about recent allegations that he’d engaged in witness tampering.

“This is not the first time we’ve had to talk about the rules, and about you skating close to the line,” Judge Amy Berman Jackson said. “All the defendant has said to me is, ‘Well, there wasn’t a clear enough order saying not to do it.’”

It was June, his jail-term was temporary, and the first of two trials still loomed like a thundercloud out in front of him. But the judge might have been talking about his entire, at times improbable, career.


Manafort made millions “skating close to the line,” advising foreign dictators and helping rewrite the rules of lobbying in Washington. But as he arrives in a Virginia courthouse Tuesday for the first of two trials against him, he’s up against a formidable opponent: Special Counsel Robert Mueller and the U.S. federal government.

Facing a case built on a lengthy paper trail and testimony from his former right-hand man, ex-colleagues, accountants, bankers, real estate agents, and FBI and IRS officials, Manafort’s refusal to seek a deal with prosecutors suggests he may be betting his final years on a pardon from President Trump, legal analysts who reviewed his case told VICE News.

“It’s a very high-risk strategy,” said Jens David Ohlin, Cornell Law Vice Dean and an expert in international criminal law. “He’ll either face a very sad ending to his entire life, or get the last laugh. His approach seems very much in keeping with his character. It’s what made him rich.”

At 69 years old, conviction in either of his two cases could easily send Manafort to jail for the rest of his life. His decision to fight the charges against him may represent the biggest gamble yet in a life spent pushing the envelope of what politics, and the law, will allow.

Pushing the envelope

Those efforts, so far, have paid Manafort huge dividends.

The son of a small-town mayor in New Britain, Connecticut, Manafort went from the Ronald Reagan administration to become a revolutionary lobbyist and political operative in the 1980s. Along the way, he dipped in to help out the presidential campaigns of Gerald Ford, Reagan, George H. W. Bush and Bob Dole.


In the 1980s, Manafort launched a Washington consulting firm that brushed aside conventions by fusing together the once-separate spheres of lobbying and political consulting. It was a bold move that changed how Washington operates. By the end of the decade, he turned up to a Congressional hearing about corruption in politics to announce that “influence peddling” was pretty much his job description — in an admission seen as so brazen, it made the evening news.

“He’ll either face a very sad ending to his entire life, or get the last laugh.”

From there, Manafort went global, scoring lucrative contracts to advise some of the world’s most notorious dictators, like Zaire’s Mobutu Sese Seko and the Philippines’ Ferdinand Marcos — a group so disreputable that one DC non-profit labeled Manafort’s firm part of a “torturer’s lobby.” Again, Manafort, who according to documents released in his case headed the firm’s foreign department, was taking a big reputational risk, being paid handsomely to do so — and getting away with it.

Michael Caputo, a former Trump campaign communications aide, described his longtime acquaintance Manafort as a master of pushing the envelope — with a finely-tuned sense of what the law will allow.

“Paul is an envelope expert: he knows exactly where the edge of it is,” Caputo told VICE News. “For the 35 years I’ve known Paul Manafort, he’s always seen the bright line, and has never crossed it. The question here is whether the government will be able to make the case that he has.”


The bright line

Former Trump campaign manager Paul Manafort arrives for arraignment on a third superseding indictment against him by Special Counsel Robert Mueller on charges of witness tampering, at U.S. District Court in Washington, U.S. June 15, 2018. REUTERS/Jonathan Ernst

Manafort now faces two trials that rest on the question of whether he pushed his political career too far. Both stem from the decade he spent as a consultant for former Ukrainian president Viktor Yanukovych.

Manafort’s work engineering Yanukovych’s rise from disgrace up to the country’s highest office may represent his most improbable success so far.

When Manafort arrived in Ukraine in the mid-2000s, Yanukovych was tarred by accusations that he and his Russia-backed allies had tried to steal Ukraine’s 2004 presidential election — sparking a national revolt known as the Orange Revolution that swept his enemies to power.

“Paul is an envelope expert: he knows exactly where the edge of it is.”

“Yanukovych was ruled politically dead by late January 2005,” John Herbst, former U.S. Ambassador to Ukraine, told VICE News. “Here was the guy who’s team had tried to steal the election, and they failed.”

Privately, even Manafort agreed Yanukovych’s political career was doomed. In a 2005 letter sent to Ukrainian oligarch Rinat Akhmetov, released last week in court filings, Manafort noted survey results showing 87 percent of Ukrainians didn’t want Yanukovych to ever serve as Prime Minister again.

Read: Exclusive: “Sex Huntress” says she won’t give U.S. officials secret tapes about Russian election meddling

“The ability of Yanukovych to help lead a campaign against the current administration will not only fail, but it will never gain any traction,” Manafort wrote.


Outwardly, however, Manafort appeared undaunted. Arriving on the scene, he presented himself to Herbst as the guy who’s “going to help Yanukovych win the old-fashioned way, by out-organizing the opposition,” Herbst told VICE News.

Court filings presented ahead of Manafort’s trial show how involved Manafort really was, including drafts of speeches and detailed planning memos sent by the American consultant to his Ukrainian boss.

READ: Paul Manafort, a mysterious Russian jet, and a secret meeting

By 2010, Manafort achieved a feat many had thought impossible. Yanukovych was elected president, earning Manafort a reputation in Ukraine as a bonafide political genius.

Manafort went on to help steer Ukraine’s foreign policy with the same assertiveness that had brought him to a position of power.

Oleg Voloshyn, who served as spokesman for Yanukovych’s foreign ministry, told VICE News he once got into an argument with Manafort over how to respond to a statement by a European Union ambassador that was seen as unfriendly to Ukraine.

Voloshyn favored a milder approach. Manafort wanted to take a stand.

“The EU is just trying to fuck you up,” Manafort argued, according to Voloshyn’s memory of their conversation. A weak response, Manafort said, would only signal to the EU that “you like being fucked that way.”

Read: The Hapsburg Group: Paul Manafort’s shadowy, European network, explained

In the end, Manafort won. But his work guiding Ukraine’s foreign policy has also come back to haunt him. In a separate trial to begin in September in Washington DC, he stands accused of organizing a shadowy group of former senior European politicians and DC lobbyists to pursue Ukraine’s interests in the U.S., without declaring those activities to American authorities.


The Case against Paul J. Manafort, Jr.

Manafort’s political career may be the backdrop of his trial in Virginia this week, but the charges all concern his finances.

According to the indictment, Manafort and his “right-hand man,” Rick Gates, raked in tens of millions of dollars while working for Yanukovych, which they funneled through offshore companies to fund lavish lifestyles — without paying American taxes.

“In many ways, Manafort is collateral damage from Hurricane Trump.”

“Manafort, with the assistance of Gates, laundered more than $30,000,000, income that he concealed from the United States Department of the Treasury, the Department of Justice, and others,” the indictment says. Manafort allegedly disguised the funds as “loans” from the companies he controlled.

Manafort bought homes in Brooklyn, Manhattan, the Hamptons and Virginia — which he tricked out with antique rugs, audio-video systems and over half-a-million worth of landscaping.

But in 2014, Yanukovych’s government collapsed. Manafort’s lean years set in, and he set out to find another way to raise cash, according to Mueller’s team. He allegedly turned to funding his lavish lifestyle with loans from American banks, using the properties he’d purchased in his salad days as collateral — and by filing misleading loan applications.

“Manafort and Gates fraudulently secured more than twenty million dollars in loans by falsely inflating Manafort’s and his company’s income and by failing to disclose existing debt in order to qualify for the loans,” the indictment says.


Though Manafort’s work for Trump may have little to do with the charges against him in Virginia, it's cast an undeniable shadow over the legal proceedings.

Read: The Mueller probe is hammering Trump’s allies with insane legal bills

“Even a blind person can see that the true target of the special counsel’s investigation is President Trump, not defendant,” Judge T.S. Ellis wrote in June. “Specifically, the charges against defendant are intended to induce defendant to cooperate with the special counsel by providing evidence against the President or other members of the campaign.”

Despite Manafort’s lifetime of envelope-pushing, this trial probably never would have happened if Manafort hadn’t decided, in the early days of 2016, to team up with the Trump campaign, said Paul Rosenzweig, who was senior counsel for the Ken Starr investigation into former President Bill Clinton.

“In many ways, Manafort is collateral damage from Hurricane Trump,” Rosenzweig told VICE News. “I doubt Manafort’s activities would have become the subject to this kind of scrutiny if he hadn’t joined up with Trump. He probably would have succeeded in skating underneath the radar until he died.”

But given the apparent strength of the case against Manafort, Rosenzweig said he sees two most likely reasons why Manafort hasn’t pled guilty and agreed to cooperate with Mueller.

“The window to make a deal and cooperate is narrowing, but it’s not yet closed.”


Manafort appears to be either banking on a pardon from Trump, Rosenzweig said — or else he hasn’t got any real evidence of collusion with Russia to trade with Mueller for his freedom.

Cornell’s Ohlin agreed.

“I’ve expected him to make a deal with prosecutors, but it seems that either he’s waiting for a pardon, or, possibly, he doesn’t have the explosive evidence Mueller wants,” Ohlin said.

If Manafort is gambling the end of his life on a pardon from the famously unpredictable President Trump, then his strategy in this case appears to represent the greatest wager yet in a life spent winning unlikely bets — pushing all of his chips to the middle of the table.

He may, however, have an ace up his sleeve: If Manafort does have truly damning evidence linking Trump to the Kremlin, he could potentially use it to bargain with Mueller even after he’s been convicted, said Ohlin.

“The window to make a deal and cooperate is narrowing, but it’s not yet closed,” he said. “You’d have to have something very compelling to offer the prosecution at that point.”

Cover image: Paul Manafort, former campaign manager for U.S. President Donald Trump, leaves a U.S. District Court after attending a motions hearing in Washington, D.C., U.S. April 19, 2018. REUTERS/Carlos Barria