Michael Kruse is a senior staff writer for POLITICO.

One of Donald Trump’s most important mentors, one of the most reviled men in American political history, is about to have another moment.

Roy Cohn, who has been described by people who knew him as “a snake,” “a scoundrel” and “a new strain of son of a bitch,” is the subject of a new documentary out this week from producer and director Matt Tyrnauer. It’s an occasion to once again look at Cohn and ask how much of him and his “savage,” “abrasive” and “amoral” behavior is visible in the behavior of the current president. Trump, as has been well-established, learned so much from the truculent, unrepentant Cohn about how to get what he wants, and he pines for Cohn and his notorious capabilities still. Trump, after all, reportedly has said so himself, and it’s now the name of this film: “Where’s My Roy Cohn?”


What Cohn could, and did, get away with was the very engine of his existence. The infamous chief counsel for the red-baiting, Joseph McCarthy-chaired Senate subcommittee in the 1950s, Cohn was indicted four times from the mid-’60s to the early ’70s—for stock-swindling and obstructing justice and perjury and bribery and conspiracy and extortion and blackmail and filing false reports. And three times he was acquitted—the fourth ended in a mistrial—giving him a kind of sneering, sinister sheen of invulnerability. Cohn, Tyrnauer’s work reaffirms, took his sanction-skirting capers and twisted them into a sort of suit of armor.

It’s the past quarter or so, though, of Tyrnauer’s film that is perhaps most salient at this stage of Trump’s first term. It deals with the less discussed but arguably much more trenchant lesson of Cohn’s life—not his decades of dark-arts untouchability but his brutal comeuppance. Cohn did not, in the end, elude the consequences of his actions. He could not, it turned out, get away with everything forever. He was a braggart of a tax cheat, and the Internal Revenue Service closed in; he was an incorrigibly unethical attorney, and he finally was disbarred; and only six weeks after that professional disgrace, six months shy of 60 years old, Cohn was dead of AIDS.

Now, less than 14 months out from next year’s election, with Trump facing historic legal and political peril, it’s getting harder and harder not to wonder what he might or might not have gleaned from watching Cohn’s wretched unraveling. Trump is beset by 29 federal, state, local and congressional investigations. Poll after poll shows he’s broadly disliked. He could win reelection, obviously, but it’s true, too, that he’s an unusually endangered incumbent. Trump, to be sure, is not weakened by physical sickness, and he has not been pursued by prosecutors and other committed antagonists for nearly as long as Cohn was. And as powerful as Cohn was perceived to be at his peak, he was never, it almost goes without saying, the most powerful man in the world. Even so, the question looms: Will Cohn’s most accomplished and attentive mentee ultimately suffer a similar fate?

“The maddening thing about Cohn and Trump,” Tyrnauer told me recently, “is that they have this sort of Road Runner-versus-Wile E. Coyote knack, where you think the boulder is going to fall on them and crush them and they escape just in the nick of time.”

“There’s a certain American romance to getting away with it. We all secretly admire the guy that can,” said Jim Zirin, a former federal prosecutor who is a regular interviewee in the film and also has a book coming out next week, Plaintiff in Chief: A Portrait of Donald Trump in 3,500 Lawsuits, in which Cohn plays an unavoidably prominent role.

“But I, as a lawyer, particularly,” Zirin added, “believe in justice, and I believe that at the end of the day, sooner or later, everyone has to pay for it.”

Just look at Cohn.

“We had him. He wasn’t getting out of this,” Martin London, one of the lawyers who led Cohn’s disbarment, tells Tyrnauer. “He was a pinned moth.”



***

The government long had tried to take him down, “a vendetta,” Cohn thought, for his role with McCarthy—and he had not fallen, or so much as flinched, and it had granted him, as a New York politician put it in Newsweek, a certain “jugular mystique.” Many came to view his checkered record as not noxious but enticing.

“He was a prototypical Teflon man,” Zirin writes in his book. “The more unscrupulous he became, the more his law practice grew. He was the man to see if you wanted to beat the system.”

“He did whatever he wanted, and he felt he was good enough at everything to get away with it,” Robert Cohen, who worked with Cohn at his firm, says in the film, “and he did for a very, very long time.”

“Roy,” according to an attorney in his office, “couldn’t have given less of a shit about rules.”

“I decided long ago,” Cohn once told Penthouse, “to make my own rules.”

He was acquitted in ’64, and he was acquitted in ’69, and he was acquitted in ’71, all the while thumbing his nose at the feds, but Cohn’s screw-you stance was a lifelong philosophy, entitlement plus boldness.

He was “an incredibly spoiled princeling of an only child,” Cohn cousin David Lloyd Marcus told me. “He always got his way,” recalled his favorite aunt. As an adult, the resting expression on his face, which was marred by a scar that ran like a scrape down the middle of his nose, was a mixture of “arrogant disdain” and a “whipped-dog look,” people observed, “caught somewhere between a pout and a challenging glare.”

He didn’t pay his bills, all but daring his creditors to sue him for what he owed—tailors, locksmiths, mechanics, travel agencies, storage companies, credit card companies, stationery stores, office supply stores. He didn’t pay people back, “friend or foe,” wrote his biographer, Nicholas von Hoffman, who reported that a captain of his yacht called Defiance “had a mental map” of “ports we couldn’t go into because we owed thousands of dollars.”

He didn’t pay his taxes, either, racking up millions of dollars in liens. Taxes, he believed, went to “welfare recipients” and “political hacks” and “bloated bureaucrats” and “countries whose people hate our guts.” He ceaselessly taunted the IRS, calling it “the closest thing we have in this country to a Nazi or Soviet-type agency”—subpoenas from which, he said, went straight into “the wastebasket.”

He drank champagne spiked with Sweet’n Low and habitually picked food off other people’s plates, thinking that manners for some reason did not apply to him. He told his chauffeurs, the drivers of his Bentley and his Cadillac and his money-green Rolls-Royce, to run red lights. “Just go!” he would yell, reaching over to the steering wheel and pounding on the horn.

He was preening and combative, look-at-me lavish and loud. It was an act. The truth was he hated what he was—a lawyer who hated lawyers, a Jewish person who hated Jewish people, and a gay person, fiercely closeted if haphazardly hidden, who hated gay people, calling them “fags” and expressing his conviction that “homosexual teachers are a grave threat to our children,” according to both his biography and autobiography. In his book, Zirin calls Cohn “a quintessential hypocrite, a classic Tartuffe.” He wanted the world to see only the person he “shaped and invented,” in von Hoffman’s words, “a secret man living a public life.”

And as a litigator, Cohn had earned a reputation as “an intimidator and a bluffer,” attorney Arthur Liman would write, “famous among lawyers for winning cases by delays, evasions, and lies.” He was unorganized and largely disinterested in specifics, relying less on preparation and more on his belligerence and his vast, nonpareil network of social and political connections that spanned parties and stretched from New York pay-to-play clubhouses to the backrooms of Washington as well as the Oval Office.

“People came to me,” Cohn explained in Penthouse, “because my public image was that I was unlike most other lawyers. Not the typical bill-by-the-hour, do-nothing, cover-up shyster but someone who won’t be pushed around.” His clients called him a “pit bull” and “a shield” and included mob bosses who met in his office to use attorney-client privilege to dodge potential wiretaps. “He’ll bend the rules to the limit,” a New York law professor once told Newsweek. “He will stop at nothing,” a law school classmate once told Esquire.

His biographer likened him to Houdini.

Cohn, however, preferred a different comparison. “If you can get Machiavelli as a lawyer,” he once said, “you’re certainly no fool of a client.”

He was roundly, practically fetishistically unapologetic, remorseless, shameless, “totally impervious to being insulted,” said gossip columnist Liz Smith, living by a code of blunt, come-at-me audacity, accessible only to those unhampered by morality.

“He made his legal and political career,” in the estimation of the British historian Eric Hobsbawm, “in a milieu where money and power override rules and law—indeed where the ability to get, and get away with, what lesser citizens cannot, is what proves membership of an elite.”

“Cohn,” Pulitzer Prize-winning columnist Murray Kempton wrote, “brought an aura perfectly calculated to attract rich men who are not quite respectable.”

Trump found him irresistible.



***

“Trump,” the late Wayne Barrett wrote in 1979, “is a user of other users”—a keen, foundational insight, true then and true now. And with the exception of his father, whose fortune made possible the life he’s lived, Trump used Cohn more than he used anybody.

From 1973, when Cohn started representing the Trumps after the Department of Justice sued them for racist rental practices at the thousands of apartments they owned, through the rest of the ’70s and into the ’80s, when he served as an indispensable macher for Trump’s career-launching maneuvers, Cohn became for Trump something much more than simply his attorney. At a most formative moment for Trump, there was no more formative figure than Cohn.

Tyrnauer and Zirin remind viewers and readers that Cohn imparted an M.O. that’s been on searing display throughout Trump’s ascent, his divisive, captivating campaign, and his fraught, unprecedented presidency. Deflect and distract, never give in, never admit fault, lie and attack, lie and attack, publicity no matter what, win no matter what, all underpinned by a deep, prove-me-wrong belief in the power of chaos and fear.

Trump was Cohn’s most insatiable student and beneficiary. “He didn’t just educate Trump, he didn’t just teach Trump, he put Trump in with people who would make Trump,” Marcus, his cousin, told me. “Roy gave him the tools. All the tools.”

“He loved him,” early Trump Organization executive Louise Sunshine told me.

Why?

“He was ruthless.”

So, though, was Trump.

Cohn was diagnosed as HIV-positive in October 1984. He insisted his illness was liver cancer. “Even at the end, he refused to admit that he was gay,” Wallace Adams, one of his boyfriends, tells Tyrnauer, “and he refused to admit that he had AIDS.” But everybody who knew him knew. And when Cohn’s feared, famed capacities started to sag, as he grew more and more weak and less and less useful, Trump began to transfer work to other attorneys. He called Cohn on occasion to express encouragement. He invited him to Mar-a-Lago for a dinner with others. But these gestures failed to paper over what some close to Cohn considered Trump’s effective abandonment. “Dropped him like a hot potato,” Cohn’s secretary, Susan Bell, told me. “He really did.”

By the end of 1985, Cohn was pale, frail and gaunt. His right eye was a maze of red lines. His mind wandered often, and his voice wavered to the point of a whisper. He would use one hand to stop the other from shaking. At his annual New Year’s Eve party, limos double-parked outside his Upper East Side townhouse, the A-list guests ran the gamut as usual, from onetime Tammany Hall heavy Carmine DeSapio to gossip columnist Cindy Adams to celebrity artist Andy Warhol. Cohn bucked up enough to don a white dinner jacket with a red bow tie with sequins but fooled nobody. “God,” thought Warhol, according to his diary, “he looked so sick.”

His physical diminishment ran parallel to his legal jeopardy, gutting him of the wherewithal to mount the kind of fight for which he had been so vaunted. The IRS mobilized to seize the townhouse and his cottage in Greenwich, Connecticut, filing for $7 million in back taxes. Circling, too, was the New York State Bar, bringing to a head its three-year-plus disbarment proceedings based on accusations of “dishonesty, fraud, deceit and misrepresentation,” stemming from four separate cases over the course of three decades—that he didn’t pay back a loan from a client until disbarment was underway, that he misappropriated escrowed property of a client, that he forged a signature on a client’s will, and that he lied on his application to the Washington, D.C., bar.

Trump, along with New York Yankees owner George Steinbrenner, TV personality Barbara Walters, attorney Alan Dershowitz, conservative columnists William Safire and William F. Buckley and others, testified on Cohn’s behalf as a character witness. But in late June, Cohn was disbarred. His conduct, according to the top appellate court in the state, was “unethical,” “unprofessional” and “particularly reprehensible.” In public, he remained tough-front defiant. He called those who had made the decision a “bunch of cheap politicians,” a “bunch of yo-yos,” a “bunch of nobodies.” He said he “couldn’t care less.” He said it “doesn’t bother me in the least.” But he cared a great deal. And it bothered him a lot. He talked to law partner Thomas Bolan and cried. He knew what was coming. He wrote a will and tried to “finish it” but fumbled pitifully with a bottle of pills.

Early that July, his secretary saw him just once. “I had come in the front door, and he was just descending the stairs,” Bell told me. “And he was just coming down, and he had a man on either side of him helping him walk, and he was very, very thin. You could see every bone in his ugly face, and he had thrush all around his lips. And as I walked by him—I had to go by him to get to the elevator—he looked up at me, and he said, ‘Hello, Sue.’ And I said, ‘Oh, hi, Mr. Cohn.’ And I got on the elevator, and I cried. And I didn’t like him, but I’ve never seen anybody so devastated.”

A month later, Cohn was dead.

A crowd, his crowd, of some 400 people assembled for his memorial service at Town Hall, the landmark New York venue. Bolan and DeSapio and former mayors and borough bigwigs and businessman Bill Fugazy and Republican Senator Chic Hecht of Nevada and Rupert Murdoch and Roger Stone. And Trump. They remembered him as loyal and funny and smart. They remembered him as an anticommunist patriot with an “almost insatiable interest in gossip.” Bolan eulogized Cohn as a victim of “the liberal establishment,” of “foes in the media,” of “political enemies” who “tried to shoot him down.” Fugazy said his longtime friend had “hopped the tables” until he finally was felled. He said Cohn had “lived life at the edge of danger.” Trump did not speak. He wasn’t asked. He stood instead in the rear of the room, contemplating, perhaps, all that Cohn had done for him, and who might be able to replace him, who could build on what Cohn had bequeathed. But there was just one Roy Cohn, and Trump, even at 40, maybe more than anybody, had to know it.

Cohn’s cousin doesn’t believe in karma, but he can’t help but think there is a final reckoning. “You can only outrun that fortune, and your own mistakes, and your own ego, and your own nastiness,” Marcus told me, “for so long.”

“The open question,” Tyrnauer said when we talked, “is whether Trump’s luck will hold up or whether—like Cohn—he’ll run out of road and face a tsunami of legal difficulties that will diminish him or put an end to the game that he’s played so effectively.”

“We were all brought up to believe, whether it’s an eye for an eye, it’s religion, it’s Greek tragedy, it’s whatever, that justice is going to catch up with everybody,” Zirin added. “The jury’s still out on Donald Trump. We don’t know whether he’ll get his comeuppance.”

But Tyrnauer reiterated the last lesson of Cohn.

“He got away with it,” he said, “until he didn’t.”