Paul Manafort has guided dictators and strongmen, but can he manage Donald Trump?

Reporting from Washington —  Political consultant Paul Manafort was so renowned in Ukraine for helping elect President Viktor Yanukovich that when strategist Roger Stone arrived years later to counsel another aspiring Ukrainian politician, that candidate — as Stone tells it — gave him the once over and asked: “So, you are our Manafort?”

Long a legendary figure in Washington, Manafort has spent a career guiding powerful politicians to office. As a young Republican, he organized for Ronald Reagan. Later, Manafort advised some of the world’s most notorious figures, including Philippine dictator Ferdinand Marcos and Angola guerrilla leader Jonas Savimbi.

His experience in guiding strong-willed men with big egos and overpowering personalities should serve him well in his role managing Donald Trump’s campaign for president. But some are beginning to wonder whether this time Manafort may have met his match.

“He has an impossible task,” said Vin Weber, a former Republican congressman who now works as a political consultant.

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On Monday, though, it was Manafort who was thrust into the spotlight. A New York Times story raised fresh questions about possible secretive cash payments for his work in Ukraine – an account Manafort dismissed as “silly.”

But with time narrowing to repair Trump’s standing in the polls, the attention on Manafort provided an unwelcome distraction that could undermine his effort to salvage the campaign.

Taking on Trump offers a second act for the seasoned GOP operative who was a leading player in Republican circles during an earlier era in Washington, before organic restaurants replaced dimly lit steakhouses as the capital’s favored after-hours haunts.

Black, Manafort, Stone and Kelly – the firm he operated in the 1980s with Stone, Democrat Peter Kelly and Charlie Black, another longtime GOP advisor to former Presidents Reagan and George H.W. Bush – was known for its hard-charging political and business lobbying. Trump was one of Stone’s clients.

The firm has long since disbanded, and Manafort hasn’t run an election in the U.S. for years. When he was brought in to help Trump this spring, some younger GOP operatives scoffed at his reemergence.

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Donald Trump delivered a group of economic proposals at the Detroit Economic Club on Monday.

At the time, though, it became clear Trump needed a midcourse correction to salvage his unpredictable rise. He had been losing ground in the bitter primary battle, and Manafort, who had run delegate operations dating back to Gerald Ford, was seen as a skilled strategist who could steer Trump through what was then looking like it might be a dicey convention nominating contest.

The veteran strategist quickly became the adult in the room. Campaign manager Corey Lewandowski was abruptly fired, and Manafort took over operations – namely, the seeming impossible job of trying to keep Trump on script.

“Manafort’s pretty good at looking around corners – what’s going to happen,” said Scott Reed, senior political strategist at the U.S. Chamber of Commerce, who was groomed by Manafort during Reagan’s 1984 reelection campaign and later hired his old boss to run the 1996 GOP convention in San Diego that nominated Bob Dole for president.

“This guy’s one of the most competitive guys I know,” Reed said.

At 67, Manafort now finds himself in a younger man’s game. He has appeared tired at times, bags under his eyes, his tailored image sometimes undone by the need for a haircut.

Some recent reports suggest that Manafort has become frustrated with Trump’s undisciplined style and unwillingness to stay on message – most disastrously his verbal and Twitter assault on the parents of a U.S. Army captain killed in Iraq.

But some close to Manafort downplay such concerns.

“I’ve talked to him,” said Black, who still keeps in contact with his old business partner. “He is fully determined. Presidential campaigns are the Super Bowl, and to have a chance to run one [is] a big deal for him. He’d just like to win.”

Even so, others believe there still may come a tipping point at which a veteran pro like Manafort has had enough.

For example, members of Trump’s team publicly contradicted Manafort when he repeatedly denied that Melania Trump’s convention speech had been plagiarized, only to have the campaign later admit that parts were lifted from a Michelle Obama speech.

“I can’t imagine Paul Manafort just sitting back, going over the cliff with Donald Trump,” said Weber, who is not supporting Trump for president. “If he comes to the conclusion his candidate is hopeless, the campaign is hopeless, he would disassociate himself. And I wouldn’t blame him. Why be the guy who gets the blame for a candidate who cannot conform?”

Manafort has always enjoyed a bit of an enigmatic reputation as a background fixer known for staying out of the spotlight despite operating at some of the highest levels of Washington power politics.

He keeps a home in the Washington suburbs and a Manhattan apartment in Trump Tower, according to those who know him. But his work is sometimes difficult to trace.

The campaign did not respond to a request for an interview.

His Trump work is volunteer, he has said.

Manafort’s compensation in Ukraine is not easily documented in federal lobbying databases, but has been investigated by reporters at PolitiFact and other media organizations. Some of his earlier arrangements with foreign clients have been documented by the Center for Public Integrity.

His foreign ties have increasingly come under scrutiny largely because of Trump’s own business interests abroad and his public praise of Russian President Vladimir Putin, despite Russia’s widely criticized annexation of the Crimea region of Ukraine in 2014. Trump has also questioned whether as president he would automatically defend NATO allies in the event of Russian aggression.

After the Republican National Committee broke with GOP orthodoxy to soften the party’s platform language on Ukraine – saying the U.S. would support, but not arm the Kiev-based government – Manafort denied that he or the campaign played a role or was seeking to make the platform more pro-Russian. He told NBC News’ Chuck Todd he did not even know of the change until after it was made before the convention in Cleveland.

Manafort recently defended his Ukraine work on behalf of Yanukovich as helping to strengthen the country’s ties with the West.

“I don’t think Yanukovich was the pro-Putin person that he’s reputed to be,” he told talk-show host Charlie Rose, who reminded him that the Ukrainian leader fled to Russia after being booted from power.

On Monday, the New York Times reported that a newly formed Ukraine anti-corruption bureau is investigating documents that appear to show cash payments designated to Manafort by Yanukovich’s political party. Investigators have yet to determine if he ever received the cash, the story said.

Manfort dismissed the account as “unfounded, silly and nonsensical.”

“The simplest answer is the truth: I am a campaign professional,” Manafort said in a statement. “It is well known that I do work in the United States and have done work on overseas campaigns as well. I have never received a single ‘off-the-books cash payment’ as falsely ‘reported’ by The New York Times, nor have I ever done work for the governments of Ukraine or Russia.”

Supporters warn against underestimating Manafort.

Stone, who bonded with Manafort when they were students , recalled his own 1977 run for chairman of the Young Republicans, a national federation of political groups aligned with the GOP.

Stone faced a tough challenger from Chicago, and Manafort set out to have a chat with the opponent over dinner. He returned with word that he had persuaded the candidate to join Stone’s slate -- as a running mate.

Manafort and Stone went on to help elect Reagan in 1980 — with Manafort leading a Southern strategy focused on turning white working-class Democrats into Republicans, an effort Trump’s campaign is trying to duplicate elsewhere today.

“He is an extremely tough guy,” Stone said. “He’s not a quitter. He’s a fighter. He realizes this is a long game.”

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Twitter: @LisaMascaro

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UPDATES:

11 a.m Aug 15: This story was updated with the recent controversy involving Manafort’s work in Ukraine.

This story was originally published Aug. 12 4 a.m.