Donald Trump rarely misses an opportunity to boast to potential voters about his wealth. But Paul Manafort — Trump’s just-demoted former campaign manager, who as campaign chairman continues to coordinate the candidate’s establishment outreach — is vastly wealthy in his own right. While Manafort almost never discusses the sources of his riches — particularly his work in the past decade and a half selling Viktor Yanukovych, the disgraced former president of Ukraine, and his Party of Regions — they have become a serious campaign issue for Trump.

There’s a lot of confusion about exactly what Manafort did for Yanukovych and the Party of Regions, as well as how much he got paid, between 2005 and 2014. A New York Times story earlier this week, citing Ukraine’s newly formed anti-corruption bureau, raised questions about alleged under-the-table cash payments of $12.7 million to Manafort from Ukrainian government clients. Investigators assert that the disbursements were part of an illegal off-the-books patronage system, which at points used industrial companies and shell corporations to divert government money to friends and colleagues, including election officials.

As part of a larger ongoing investigation into Manafort’s Ukraine activities and their impact on U.S. politics, Fusion has found a number of massive real estate and Hollywood film investments by Manafort in the time period covered by the Times’ alleged Ukrainian cash payments to him, between 2007 and 2012.

It’s impossible to glean from public records how much money Manafort made during his foray into Ukraine, since he didn’t register as a foreign lobbyist. But Fusion has also spoken to half a dozen former U.S. government officials or lobbyists familiar with Manafort’s work for Yanukovych. They couldn’t say for sure whether he had breached lobbying disclosure laws — they simply didn’t have enough details — but they unanimously stated that he was aggressively seeking to polish the strongman’s image in Washington, not just Kiev. For example, Manafort helped arrange meetings for Yanukovych with U.S. government officials, including then-Vice President Dick Cheney in 2007.

Except for one lobbyist, Fusion’s sources asked not to be identified out of fear of alienating former clients and losing future business.

“He definitely lobbied for him in Washington, that’s part of what he brought to the table,” said a former high-ranking American diplomat who told Fusion he was lobbied by Manafort. “He had great contacts in DC.” The diplomat said that Manafort “tried to sell Yanukovych as being an advocate of transparency, democracy, and generally pro-American.” Manafort, he added, would inevitably note that in the past he had worked for Republican presidential candidates such as Bob Dole and Ronald Reagan. “He’d say Yanukovych was the more or less the same sort of person…with good-old fashioned Republican values,” he said.

Manafort and other representatives of Trump’s campaign did not respond to Fusion’s multiple requests for comment on this and upcoming stories; In a press release disputing the Times’ account, Manafort stated that the “suggestion that I accepted cash payments is unfounded, silly and nonsensical.” But Fusion’s investigation raises questions about the extent to which Manafort profited from the selling of a strong-arm overseas politician and sidestepped the United States’ nominal requirements for transparency in foreign lobbying activities.

Questions about propriety… and property

There are two major reasons that so many questions remain about the nature of Manafort’s work for Yanukovych and the Party of Regions. The first is simple: Manafort has refused to describe it. Much of what is known emerged only after Yanukovych fled Ukraine in 2014, ousted by a popular revolution, and volunteer divers retrieved thousands of internal government documents that had been hastily thrown into a lake at his presidential retreat. Additional paperwork was found tossed inside a Ukrainian prosecutor’s sauna. The documents were dried and assembled by local journalists; some offer details on Manafort’s role in Yanukovych’s reign, helping to coordinate a U.S. law firm’s favorable inquiry into Yanukovych’s arrest of a political opposition leader.

The second and related reason is that U.S. disclosure laws for foreign lobbyists are riddled with exceptions and almost entirely unenforced, and Manafort didn’t register. “Any Washington insider with an ounce of intelligence and common sense can easily evade lobby disclosure requirements,” Meredith McGehee, policy director for the nonpartisan Campaign Legal Center, said in an interview. “You have to be really dumb to get caught.”

Political consulting work for foreign clients does not need to be disclosed unless the work takes place in the United States. Furthermore, foreign lobbyists only need to disclose their activities if their advocacy takes up more than 20 percent of their work for the clients — and then only if they are discussing a narrowly defined set of issues, such as a foreign aid bill or other specific legislation.

Manafort’s work in Ukraine coincided with the purchase of at least four prime pieces of real estate in the United States, worth a combined $11 million:

A corporation registered to Manafort in Florida bought a former JetBlue CEO’s two-bedroom Trump Tower condominium for $3.7 million in November 2006.

In September 2007, he purchased a 4,000 square-foot home in Palm Beach Gardens, half an hour north of Trump’s Mar-a-Lago residence, for $1.7 million. The waterfront home has “the feel of a private tropical island; plus fabulous views of the golf course,” according to an old sales listing.

In October 2007, another of Manafort’s Florida-registered companies, JESAND LLC – an apparent portmanteau of the names of Manafort’s daughters, Jessica and Andrea — bought a 2,100 square foot luxury condo in Manhattan’s Soho neighborhood for just over $2.5 million. In addition to Brazilian cherry wood floors and an attractive tax abatement, the apartment offered “oversized terraces suitable for sun bathing or spring planting,” according to a broker’s listing.

A third Florida corporation of Manafort’s closed on another 2,100-square-foot “full-floor” SoHo loft for nearly $3 million in early 2012. A broker’s listing says the apartment, in a 5-unit building, boasts “remarkable open sky and city views looking north up the full length of coveted Crosby Street.”

Manafort’s lucrative consulting work enabled him to make large real estate purchases before and after his Ukrainian work. His U.S. real estate portfolio included a 5,600-square-foot home in the Hamptons, currently worth more than $5 million; a 5-bedroom, 6,500 square-foot mansion in Alexandria, Virginia, which he sold in mid-2015 for $1.4 million; a new 2,800 square-foot Alexandria waterfront luxury condo, bought around the same time, for $2.7 million; and two 5-acre horse farms in Florida and Virginia.

Manafort is also listed as a co-producer of the star-filled 2005 independent film “The Dying Gaul,” a meditation on loss and homosexual domesticity that its liberal director/writer, Craig Lucas, dedicated to “Angels in America” writer Tony Kushner. A conservative movie-review website described the film as a “misanthropic humanist worldview about a homosexual and adulterous affair in Hollywood that leads to murder and death.”

Estimated to have cost $4 million to produce, the film earned just over $342,000 at box offices.

George VanBuskirk, the film’s lead producer, confirmed that Manafort had helped bankroll the film. “Manafort’s daughter wanted to build a career in film, that was his primary interest in the entertainment business,” VanBuskirk told Fusion. (Manafort’s daughter, Jessica, resides in Malibu, California, and produced and directed several short films in the mid-2000s.)

Manafort joined VanBuskirk and others in a plan to produce and distribute several films together. He “arranged a tax vehicle for ‘The Dying Gaul’ to bring in investors,” VanBuskirk said. “We got funding for the film but Paul’s company, Manhattan Pictures, ran out of money and shuttered. That ended our relationship.

“Paul pretty much disappeared from the entertainment business after that as far as I know, aside from helping his daughter with funding for her film and [getting] involved in Ukrainian politics, as you know,” VanBuskirk added.

Selling a strongarm leader

Manafort’s Ukrainian work reportedly began in 2005 when he was retained by Rinat Akhmetov, a billionaire oligarch who “is reputed to have emerged from a bloody power struggle among organized crime groups in the 1990s that sought to control the mighty coal and steel assets of the Soviet Union,” according to the New York Times. The Forbes-listed plutocrat reportedly hired Manafort to run strategic communications for one of his many companies, but multiple reports say Akhmetov connected Manafort to Yanukovych, the oligarch’s key political benefactor.

Selling Yanukovych was no small feat. As a young man, he had served two terms in prison for street robberies and other crimes; he later robbed the country blind during a three-year stint as prime minister, when in the name of state “privatizations” he’d turned the economy over to Akhmetov and other oligarchs. “This guy was a street gangster, but Manafort gave him fashion advice and bought him nice suits,” an American political consultant with experience in Ukraine told Fusion. “Manafort had to take a criminal and make him look presidential.”

That assessment was shared by a number of other sources Fusion spoke with, who were familiar with some additional details of Manafort’s work for Yanukovych. “Manafort dressed him up, gave him media training — he even hired a teacher to teach [Yanukovych] to improve his Ukrainian,” said another lobbyist with years of experience in the region. This person said that Manafort also conducted local polling to hear what were the key issues for voters, and then crafted talking points for Yanukovych to mouth to address the concerns.

The former U.S. diplomat said that most of Manafort’s work in Ukraine involved valiantly trying to make Yanukovych look more polished and presentable. “He wasn’t very articulate, in Ukrainian or Russian,” this person said. “He was crude, to put it mildly.”

But this source said that Manafort also worked Washington on behalf of Yanukovych, and made some brilliant moves. Among the sharpest, he said, was arranging a top translator to accompany Yanukovych to meetings in Washington with top government officials.

In 2007, when Yanukovych was Ukraine’s prime minister, Manafort set up meetings for him in Washington with a broad range of officials and think-tank experts in an effort to rebrand him as a reformer. According to this source, during meetings with vice president Cheney and State Department officials, the strongman’s translator comically turned the Ukrainian’s crude rhetoric into flowery, high-end English. “He took Yanukovych’s words and ideas and made both of them better,” the source said.

Other sources Fusion spoke to cautioned that the emerging media narrative of a grand alliance between Yanukovych and Russian President Vladimir Putin — and, by extension, a Manafort-Putin connection — are overblown. Yanukovych and Putin “never got along,” Jim Jatras, who did elections work for Yanukovych in the early-2000s, told Fusion. “Putin thought he was a pain in the ass.” Jatras said Yanukovych and his allied oligarchs knew they’d be “eaten alive” if they allowed Moscow to totally dominate the country; rather, he said, they sought to play Russia against the United States and the European Union. Yanukovych wanted “his friends to be able to bleed the country dry and be the king of his domain,” and Manafort helped him try to achieve that, not carry water for

Moscow, Jatras said.

Manafort apparently succeeded in making Yanukovych more appealing; he ultimately won the presidency in 2010. Meanwhile, Manafort continued to work in Ukraine until 2014. That year, Yanukovych was forced from power by popular protests, which he tried to repress by sending armed police into Kyiv’s main square. The police opened fired, killing or wounding hundreds, before Yanukovych fled for Moscow.

In the interim period, Yanukovych’s government famously arrested and prosecuted his main political opponent, Yulia Tymoshenko, on a host of corruption-related charges. Her imprisonment sidelined Yanukovych’s opposition and aroused U.S. and European human rights concerns, potentially endangering foreign support for Ukraine’s regime. To address these concerns, Yanukovych hired lawyers from the Washington offices of Skadden Arps, a prestigious white-shoe law firm, to conduct an independent inquiry into Tymoshenko’s arrest and trial.

It’s unclear whether Manafort was involved in Skadden’s hiring, but internal documents recovered in 2014 from the lake in Yanukovych’s presidential residence show Manafort helped coordinate Skadden’s review, with the law firm permitting Ukrainian officials to review and comment on an early version of its report. In one memo, Skadden’s lead investigator asked Manafort to “help in the acceleration” of information that could potentially show Tymoshenko was not cooperating with her prosecutors.

That memo was dated August 24, 2012. In September, several months before its public release, Skadden shared its report with the Ukrainian government; it concluded that Tymoshenko’s prosecution was justified.

In October 2012, Manafort’s daughter, Andrea, a recent Georgetown Law Center graduate, started work as a Skadden Arps associate in Washington – one of the most coveted, competitive entry-level jobs for top-tier law school grads – the same bureau housing the attorneys who had produced the Tymoshenko report. Ukrainian officials are investigating how much Skadden was paid for its report and who did the paying. Andrea Manafort and several Skadden attorneys who worked on the Tymoshenko report did not respond to Fusion’s requests for comment.

“That’s Washington”

There’s no question that Manafort is very good at what he does. He’s not stupid. Even in his new, limited role on the Trump campaign, Manafort is likely to hold considerable sway over policy proposals, messaging, and — obviously with limited success — getting Trump to stick to his teleprompter. “Manafort is a great manager,” one Republican political consultant and lobbyist who has known him for more than thirty years told me. “He is very organized, very smart, very professional and very urbane. He looks like he’s the CEO of a Fortune 500 firm.” He lives like one, too.

But was Manafort legally a lobbyist when he sold Yanukovych to the U.S., or not? He’s never spelled out the extent of his duties, there are no lobbying records to peruse, and the documents fished out of the lake and sauna don’t provide a full enough picture.

Manafort can’t be fully blamed for this opaque situation, since he’s one of countless Washington lobbyists and PR professionals who advocate for clients without filing, whether they should or not. “There are a lot of very high-profile insiders who go to the Hill and to government agencies and you will not find them in the lobby disclosure forms,” McGehee told me. “There’s very little incentive to do so since no one ever gets prosecuted for violating the rules.” She said she’s been shopping a package of tougher lobby disclosure rules drafted by an American Bar Association panel— the last full reform took place in the mid-1990s, after more than 50 years without any significant revision — but “there’s very little appetite for reform.”

Meanwhile, one lobbyist with extensive overseas experience — and who does file with the U.S. government regularly — expressed resentment that Manafort and some of his competitors do not disclose their work.

“It’s a pain in the ass to file, there’s a lot of paperwork and it makes you an open book for your clients’ political enemies, but you’re supposed to do it,” he said. “But the guys in the stratosphere can just ignore the rules and get away with it. That’s Washington.”

— Deirdra Funcheon and Kevin Roose provided research and reporting assistance for this story.