Active Measures director says Trump's Russian mob ties are his biggest legal vulnerability
But on Friday morning Trump put some distance between himself and Giuliani without clarifying the ever confusing details of the payment.
Those details matter because the payment could constitute a violation of campaign finance law.
Trump may be vulnerable on that front, or Robert Mueller may find evidence of collusion with Russia or obstruction that would expose the president to other charges.
Jack Bryan believes Trump's legal vulnerabilities go back even further, predating his presidency.
"I think he's got very serious legal problems," Bryan says on Day 6. But they might not be the problems raised by Stormy Daniels.
Once he loses out in Atlantic City, once he can't get a loan from a bank, that's when the Russian mafia says: 'We have an opportunity here.'- Jack Bryan, director of Active Measures
Bryan's first feature length documentary, Active Measures, takes a long look at malevolent Russian influence, but it converges on Trump, his association with Russian mobsters and the Russian money that kept him in business.
Vanity Fair asks: "Is This the Documentary That Can Take Down Trump?"
A better question might be: 'How mad will this make Putin?'
Shell companies buy condos
Active Measures shows how foreign investments made by Russian oligarchs bolster the Kremlin's ambitions to exert influence in the west. The key is money laundering — the export of Russian wealth with the knowledge and approval of Putin.
Bryan says mobsters were Trump clients as early as 1985.
"He sells three condos to a man named David Bogatin, who's a Russian mobster," Bryan says. "This is in Trump Tower. And the reason they did Trump Tower is that it was the second building in New York where a shell company could purchase a condominium. And so it makes it much more easy to launder dirty money."
When Trump's fortunes fall, the Russians smell blood.
"Once he loses out in Atlantic City, once he can't get a loan from a bank, that's when the Russian mafia says: 'We have an opportunity here,'" says Bryan.
That's when Trump becomes less of a partner for Russian mobsters and more of a mark.
Bryan's film alleges that Trump needed Russian mob money to reinvent himself after his disastrous string of bankruptcies. Without it, the film alleges, he would never have won the presidency.
"The Russians saved him. They rescued him. He would not have gotten back in business without them," journalist Craig Unger says in the film.
Bayrock Group, Sater and Cohen
After multiple bankruptcies, when most of Trump's investors had fled, a real estate firm with Russian backing moved into Trump Tower. Bryan's film sees this as a turning point, an intensification of Russian interference and a new source of wealth for Trump.
"Bayrock Group is a Russian real estate firm. The manager was this guy Felix Sater, and he is very connected to the Russian mafia," Bryan says.
Sater, a convicted felon, also has ties to Trump's recently fired attorney, Michael Cohen. Bryan says Cohen entered the Trump organization at the same time as Bayrock.
"Cohen is childhood friends with Felix Sater. They went on their first date together," Bryan says. "They did a lot of business together."
Bayrock operated from offices two floors below Trump's and partnered with him on a wide variety of real estate deals from 2002 to 2011. Bryan says Bayrock likely didn't see Trump as a political player or a potential president. They saw him as a shield.
"I think, at that point, they're seeing him as: he's a really famous guy and it's great cover because nobody's going to question a lot of money going into the Trump organization. And they knew that he needed the money. And also they knew he's really litigious. And so it would be really hard to go after him. And I think that he just became this sort of perfect place to stash money."
How money laundering could be exposed
Through this period, Sater remained in contact with his old friend Michael Cohen. A series of emails between the two, written during the campaign, appeared last year in the New York Times.
The FBI raided Michael Cohen's office and home on April 9th. Bryan says it could mark a turning point in the investigation of the president.
"I think Cohen knows just about everything," he says.
He points to the significance of the Cohen case being handled by the US attorney's office for the Southern District of New York, and recounts Trump's warning to Robert Mueller.
"The early laundering, the real serious laundering you see from 2004 all the way to 2014, that is going to be taken as a separate case by the Southern District of New York. And I think the reason for that is that Trump, at one point, said that it will be crossing a red line if he looked at his personal business dealings."
Bryan chooses to end Active Measures with images of resistance, but he warns democracy needs more action to withstand an onslaught that he describes as the organized, effective and corrupt influence exported by Russia.
"If we want to deal with this, we have to address the underlying problems," he says. "And if we do it, really, if people demand that we do that, I think that in the long run this could have been a really positive thing. If we don't, then I think we're going down a really dark path."
To hear the full interview with Jack Bryan, download our podcast or click the 'Listen' button at the top of this page.