It was the summer of 1980, and Donald Trump, a rising star in New York City real estate, trekked to Brooklyn to sit down with the Organized Crime Strike Force.

The still-lanky developer arrived alone, with no attorneys by his side, and willingly submitted himself to all of the investigators’ questions.


The FBI investigation involved a person Trump needed to ensure the speedy construction of Trump Tower: John Cody, a union boss who was being investigated for suspected mob ties. The FBI subpoenaed Trump after getting a tip that the developer had promised Cody’s supposed girlfriend a luxury apartment spread in his signature tower.

In going it alone with the investigators, according to Trump biographer Wayne Barrett, the future president tried to recast himself not as an adjunct to Cody’s scams but as a victim himself of a shakedown.

Now, as Trump continues to push to sit down with special counsel Robert Mueller — against the advice of his attorneys — the president is putting to use his same old box of tools developed during a lifetime of legal squabbles in New York City: trying to talk or cooperate his way out of things. But while he’s using the old tactics he once employed over a real estate fight, he’s also on unfamiliar turf, where the stakes of the investigation stretch far beyond any barrier he ever encountered in his business life.

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What remains, however, is Trump’s belief in his central self-created myth: that he can convince anyone of anything, if he’s simply given the opportunity to get them in a room alone.

“On the one hand, the kind of lawyers he likes are crusading, hard-hitting, very aggressive lawyers, and he uses them when he has to,” said longtime Trump associate Roger Stone. “On the other hand, he believes he’s always his best advocate.”

The New York Times has reported that Trump is pushing his lawyers for a meeting with Mueller “to clear himself of wrongdoing” and convince investigators of his own viewpoint: that the entire exercise has been a “witch hunt.”

Trump’s attorneys appear to be in late-stage negotiations over whether some arrangement in which the president answers questions can occur. Personal lawyer Rudy Giuliani told POLITICO on Tuesday that his team plans to send a letter to Mueller this week signaling they remain open to a sit-down that includes questions about obstruction of justice.

How badly Mueller needs a sit-down with Trump to complete his investigation remains a big question mark. If Trump’s team does not settle on a way to speak to Mueller, “that will likely be the moment at which Mueller has to decide whether to issue a subpoena,” said Benjamin Wittes, a senior fellow at the Brookings Institution and editor of the blog Lawfare. “It is a reasonable hypothesis that if we’re going to see one, it may happen this month.”

The idea that Trump could convince Mueller that his own investigation is the partisan trap Trump believes it to be is considered laughable by many of Trump’s own advisers. But his desire to sit with the lawyers and take his chances, those advisers said, is vintage Trump.

In 1979, for example, federal prosecutors in Brooklyn were pursuing a criminal investigation into how Trump had obtained his option to develop Penn Central rail yards. In that case, he also agreed to meet them alone, in his father’s real estate office on Avenue Z. Trump, the target of a grand jury, spoke to a prosecutor alone for 90 minutes, denying any payoff.

According to Barrett’s “Trump: The Greatest Show on Earth,” Trump, throughout the session, was “at ease and talkative.” The investigation never got to the point of an indictment, and it remained a secret until Trump wrote about it himself in his autobiography “Surviving at the Top.”

In the 1980s, when Trump expanded his real estate holdings into Atlantic City, he played the same game. His first partners along the boardwalk had ties to the Mafia, relationships that were complicating his licensing deals. On his own, Trump decided to approach the FBI and tell it he was willing to be an informant — once again, trying to assume the role of victim.

And in what has been described as the “battle of the '80s,” Trump took on the tenants association at 100 Central Park South, a building he bought in order to demolish, save for the pesky problem of rent-regulated tenants he inherited in the deal. In that dispute, Trump also approached the head of the tenants association, shocking him by explaining he wanted to meet without his lawyer to try and iron out their differences.

“If he believes he can convince someone he’s the victim, he’ll go without a lawyer,” said Trump biographer Tim O’Brien, author of “TrumpNation: The Art of Being the Donald.” O’Brien, who also served as a research assistant on Barrett’s definitive book on Trump’s rise and fall in real estate, said he and the late investigative journalist would often discuss the moments when Trump chose to bring along a lawyer, and when he chose not to.

“If he feels he’s got a winning hand to play, he will go full on attack, weaponizing the legal system with a lawyer like Roy Cohn,” O’Brien said. If not, however, he goes the victim route, and tries to use his powers of persuasion. “He thinks he can talk anyone into anything,” O’Brien said. “He believes his own myths, one of which is that he can win anyone over if he can just sit down with them and persuade.”

Some of Trump’s former lawyers said that whether Trump follows advice, or brings his counsel along for the ride, depends on the lawyer.

Jay Goldberg, who represented Trump in both of his divorces as well as his real estate deals in the 1990s, noted of his former client, “I found him 100 percent compliant with the direction of the lawyer. He listened to everything I said. He never sued anyone during the time I was with him. He was a perfect person.”

Goldberg said he has spoken to Trump only three times since his former client entered the White House. In those conversations, he has advised the president on lawyers to hire, and said he warned Trump that his former attorney Michael Cohen, who is himself under federal investigation over his business dealings, was “not the type to be able to withstand the pressures of jail.”

Goldberg said that in his experience, Trump behaved as a perfect client in response to Goldberg’s own braggadocio. “I attributed it to the strength I exhibited when I dealt with him,” he said. “I can’t say he ever acted in way to overrule the lawyer, or not follow the lawyers’ advice. I don’t know how he is now.”

