Lying, cheating and charming, spying and scamming his way through the world with a warm smile on his face and a gun tucked in his back pocket, Henry Greenberg — or whatever his name is; he uses at least four — was born in Russia. But the sun and the swindles brought him to South Florida, which is now the backdrop for the latest chapter in the seemingly endless controversy over who may have have ripped off whom in the 2016 presidential election.
Greenberg, who has left a trail of arrests halfway around the world, is the mystery man at the center of the newest report of contact between Donald Trump's 2016 campaign staff and shadowy Russians. Greenberg stands accused by Trump associates of trying to peddle derogatory information about Hillary Clinton to Trump's organization for a cool $2 million.
But if it's true, was Greenberg part of a Russian government attempt to tilt the scales of the election in Trump's favor? Or a sinister undercover shill for the FBI, trying to lure Trump's lieutenants into an illegal act for which they could be prosecuted? Or just a run-of-the-mill Russian con man trying to make a quick freelance score for himself?
The strange and captivating tale of Greenberg came to light over the weekend in The Washington Post. The Post reported that two former senior Trump campaign advisors who had previously told a congressional committee that they didn't recall talking to any Russians during the campaign both changed their testimony. They said they now remembered having fleeting contact — "a matter of minutes," one said — with Greenberg, who wanted to sell them political dirt on Clinton.
The two former advisors — Roger Stone, who now runs a Fort Lauderdale political consulting company, and Michael Caputo, co-owner of the Miami Beach-based public relations company Zeppelin Communications — said they originally dismissed Greenberg as "crazy" and a "waste of time" and promptly forgot about him. They didn't mention him when they were questioned under oath by the House Intelligence Committee as part of the burgeoning number of Washington investigations of possible collusion between Russia and the Trump campaign.
But in April, according to Caputo, as his attorney grilled him in preparation for questioning by the Senate Intelligence Committee as well as FBI agents working for special counsel Robert Mueller, Caputo suddenly remembered the encounter. Greenberg had allegedly reached out to Caputo's business partner with the offer of information, after which Caputo asked Stone to take the meeting.
His memory allegedly refreshed, Caputo told both the Senate investigators and the FBI about Greenberg — but was surprised that the FBI agents already seemed more familiar with the subject.
"Honestly, it was like they knew more about him than I did," Caputo said. "I mentioned something about how Greenberg held U.S. citizenship — I just assumed it, I don't know why — and the agent said, 'No he's not!' We went over it again and again, and the agent kept arguing about details that he clearly knew better than I did."
Figuring there had to be a lot more to the story, Caputo says he hired a Palm Beach private investigations company to look into Greenberg. "What they found were federal court documents proving, irrefutably, that he's been working for the FBI for years," Caputo said. "When he tried to sell us dirt on Clinton, it was an FBI operation. ... The FBI sent a violent, illegal-alien criminal Russian to meet with us."
Actually, the records dredged up by the P.I. don't make clear whether Greenberg was still an informant when he met with Stone in Sunny Isles Beach in March 2016, and there is an indication in the file that he may have severed his connection with the feds.
In any event, if Greenberg was indeed dangling an offer of dirt on Clinton in front of Trump's campaign at the behest of the FBI, it would call into question what the bureau has said about its investigation into alleged Russian collusion. It would mean the FBI was looking into Russians about two months before it has said its probe officially began, and long before the organization WikiLeaks began releasing hacked Democratic Party emails.
Caputo has already written to the Justice Department's inspector general, offering to share what his investigators came up with. "But it's been 10 days and I haven't heard a single word in return," he told the Miami Herald.
Not everyone agrees that potential Justice Department misbehavior is the most important thing about the Greenberg revelations. California Rep. Adam Schiff, the top Democrat on the House Intelligence Committee, told reporters that Stone's testimony "appears inaccurate or deliberately misleading" and demanded that the committee turn over the transcripts of Stone and Caputo to the special counsel for a perjury investigation.
Since the story broke, headlines have called it "yet another" contact between Trump campaign operatives and shady Russians while Caputo and Stone darkly suggest it is new evidence that the Justice Department was predisposed to go after the Trump campaign, using nefarious methods.
Although the meeting apparently produced nothing, it underscored a willingness of the campaign to meet with Russians boasting of scandalous information, Trump critics point out.
Whatever direction the investigations take, there's no denying that Greenberg has brought a dose of Florida-style weirdness to the already tempestuous tale of Russian spookery and the 2016 election. "He's a remarkable man," said Caputo, without a trace of admiration, "and it's a remarkable story."
Caputo has posted his investigators' 30-page report, including about 150 pages of supporting documents, at the unsubtly titled website DemocratDossier.org, where anybody can read them. The Miami Herald was able to authenticate some — though not all — of them, including an explosive declaration filed as part of a 2015 immigration case in a U.S. district court in California in which Greenberg says he spied for the FBI for years in return for being allowed to return to the United States after his deportation for violent crimes.
"More than eight years, while outside U.S., I provide information to [the FBI]," wrote Greenberg (under the name Henry Oknyansky, one of several he's used, according to published reports), in a plea to be granted U.S. residency. "Wherever I was, from Iran, to North Korea, I always send information."
Of course, just because Greenberg said he was a swashbuckling spy doesn't make it true. But attached to his statement were more than a dozen immigration documents known as Significant Public Benefit Paroles. The paroles allow foreigners without visas to enter the United States and stay for a certain period of time. They're typically granted to people who are witnesses in court cases or otherwise assisting U.S. law enforcement.
In the immigration case, Greenberg was arguing that the FBI had broken the terms of a deal in which he would be rewarded with an S-5 visa — similar to the parole, but good for a longer time — in return for his spying. In his statement, Greenberg said an FBI agent named David Baker had supervised his espionage work, retired in 2013 and turned him over to the bureau's Miami office.
Miami agents promised to honor the deal for the S visa, Greenberg said. But when several months passed with no action on the visa, he stopped cooperating with the FBI, which in return handed him over to the Department of Homeland Security for deportation. Instead, DHS released him into a sort of legal limbo.
"I think it's unfair," Greenberg wrote. "I cooperated with the FBI for 17 years, often put my life in danger. Based on my information, there is so many arrests, criminals from drugs and human trafficking, money laundering and insurance frauds. U.S. Treasury revoked many U.S. visas from criminal groups, for money laundering and association with international criminal entities, based on my information."
Much about Greenberg is unclear, including where he currently is and whether he had resumed working for the FBI. If he hadn't, then it could mean his offer to sell the Trump advisors derogatory information about Clinton was a private scam conducted on his own.
Which, one former federal prosecutor told the Herald, is probably what happened. The prosecutor, though he'd never heard of Greenberg, said the circumstances of his encounter with Stone indicate "it was obviously a shakedown." The ex-prosecutor, who has tried several Russian organized-crime cases in South Florida, said it is entirely plausible that Greenberg had worked for the FBI's foreign counterintelligence section. That unit doesn't ordinarily collaborate with the bureau's criminal section.
But no FBI informant, in his first meeting with a Trump operative, would open negotiations with a demand for $2 million, the ex-prosecutor said, calling it a "preposterous" sum that virtually guaranteed the approach would fail.
Caputo, however, was unimpressed with that argument. "If you want to tell me that, in the middle of 17 years of working with the FBI, the guy decided to take a coffee break to hit me up for $2 million, well, I'm not buying it," Caputo said.
The purported shakedown raises the question of where would he come up with the idea — well before anyone knew about a Russia probe — that the campaign might be interested in acquiring goods from a Russian?
The FBI itself wasn't talking on Monday. "No comment," said a spokesman for the Miami office.
Whatever went on between Greenberg and the FBI, it was only a small part of a lively if sometimes illegal existence for the Russian. According to published reports and other documents uncovered by Caputo's investigators as well as Florida public records, he's been arrested at least four times in Russia and three times in the United States, on charges ranging from assault with a deadly weapon to selling 50 million nonexistent tin cans of meat for close to $3 million.
Charges against him rarely stick, though; he bargains them down or he disappears altogether. When he was finally arrested for the canned-meat caper, 10 years after it was carried out, a Russian police spokesman wanly admitted to reporters that there wasn't much sense in writing stories about it because Greenberg (then operating under the name Gennady Vostretsov) would never go to trial.
"He seems to have powerful patrons," the spokesman said, "and he is very smart."
When Greenberg isn't getting arrested — for petty theft, for embezzlement, for drunk driving (twice, locally, in 2011 and 2016, including while doing 80 mph in a 45 mph zone in front of a Biscayne Boulevard strip club) — he's seemingly working his way into the haunts of the rich and mighty. Especially if they make movies.
In Russia, according to a report in the Moscow Times, he romanced and married an actress named Yelena Arzhanik, who won lasting fame in Russia for a movie role as a small-town secretary who worked only in the nude. Then, allegedly, he adopted her last name to help him run some cons. In 2002, the Moscow Times report indicated, he was arrested in the Russian apartment of John Daly, the award-winning producer of films "The Last Emperor" and "Salvador." In Greenberg's room, police allegedly found stacks of passport and corporate credit cards under various names, along with photos of Greenberg with Hollywood heavy hitters like Oliver Stone and Steven Spielberg.
"He has amazing skills," said a Moscow policeman at the time, according to the news report. "He is understanding and easily makes people sympathize with him. He also has a gift for instantly figuring out a person's weaknesses and using them for his benefit."
Greenberg has also lived in Hallandale Beach. And he's tried to set up shop in Miami. Going back to at least September 2016, a man who identified himself to city officials and neighboring property owners as Henry Greenberg began pushing to open a restaurant on the Miami River, where real estate is hot and waterfront eateries are spreading.
On behalf of a limited liability company called Longmore, Greenberg lobbied to convert two old buildings on the defunct Anchor Marine property on the river's south bank into a 230-seat restaurant and bar. The eatery was going to have a deck and a two-story, six-slip boatyard.
The venue has not been built, and it doesn't seem as if it ever will be. The city — which entered into a license agreement with Longmore to let the company use its property next door — granted Greenberg's LLC a special permit to build the restaurant, but neighbors appealed and won in January.
"The project has been very controversial, not only to the marine industry but also to the residents," said Horacio Stuart Aguirre, the chairman of the Miami River Commission, which voted to oppose the project. "He has indicated to me that he has other projects, but this is the only one that I’m aware of."
Tucker Gibbs, a land-use attorney who represented the Spring Garden Homeowners Association in its appeal of Longmore's restaurant, says his interactions with Greenberg were limited — and odd.
He said he first met Greenberg at Miami City Hall, where the stranger approached him and said he wanted to give Gibbs information that would benefit one of his clients. The two men played phone tag and eventually agreed to meet at Greenstreet, a popular Coconut Grove cafe, but Greenberg stood him up.
Gibbs said that later, when he represented neighbors opposed to Greenberg's restaurant, the businessman, who spoke with a "very thick Russian accent," also fell through with pledges and commitments. Then, when they appeared before the city's Planning Zoning and Appeals Board, Greenberg announced that his attorney — he claimed it was Kendall Coffey, the former U.S. attorney for South Florida now in private practice — was unavailable. And then he just walked out of the room.
"He never filed an appeal with the city, never filed a reapplication [for his restaurant]. He just sort of drifted away. I’ve never seen anything like it before in my years of working at the city of Miami," Gibbs said. "I’ve had two encounters with him and was mystified by each of them."
Coffey did not immediately respond to a voice mail left at his office Monday. Attempts to reach Greenberg by phone and text were also unsuccessful. A call to a number listed for the corporation that owns the property where Greenberg hoped to build his restaurant was not returned. Neither was a message left at a number identified as Greenberg's in a court filing.
People who dealt with Greenberg told the Herald he was cocky and "aggressive," boasting of his contacts and dropping threats when meetings and hearings didn't go his way. He made suggestions that he was politically connected, and had a mouth like a sailor when hearings on his river restaurant went poorly. But no one says they knew him well.
"There’s a national scandal," said Gibbs. "And there's got to be a Miami connection to it."