Donald J. Trump, a man adept at manipulating both the media and the political process in his favor, flourished in the 1980s New York culture of celebrity and boastful greed. But with the May 30 guilty verdict in his “hush money” case, the debt has come due for the sleazy methods of operation he adopted early in his career.

I call it the revenge of 1980s New York.

My seat for the original show was mostly in the two press rooms where I was a reporter for much of the decade: the federal courthouse in lower Manhattan, and City Hall. That experience was my lens for following the proceedings in which Trump was convicted of thirty-four felony counts of falsifying business records to suppress news—his alleged affair with pornography star Stormy Daniels at a time when his third wife, Melania, was pregnant with their son—that would have deflated his market value as a candidate for president in 2016.

Trump’s use of his longtime ties to the National Enquirer as part of the scheme was one more withdrawal from the bank account of favors he’d established long before with the gossip media. That much was established by the prosecution’s first witness, David Pecker, the tabloid’s former owner. He met Trump in the late 1980s and got him involved in backing a magazine called Trump Style. Their “mutually beneficial” relationship took a new turn after Pecker bought the Enquirer in 1999.

A bit of New York backstory here: Generoso Pope Jr., whose father owned the Italian-language paper Il Progresso Italo-Americano, purchased the failing, Hearst-financed New York Enquirer in 1952. As Jeannette Walls wrote in her 2000 book Dish: How Gossip Became the News and the News Became Just Another Show, he did so by borrowing $10,000 each from his close friend and classmate at the elite Horace Mann School, future Trump attorney Roy Cohn, and Frank Costello, the gangster who was a power in New York politics. Pope turned it into a scandal sheet filled with the goriest crime stories, but later pivoted to a new formula, as Time noted in 1972: 

In a total turnabout, the Enquirer has banished cannibalism, sadism and sick sex in favor of a blend of upbeat success stories, gossip by and about celebrities, plus an overdose of the occult and the quasiscientific. The switch to a kind of respectability has had spectacular results. Circulation, stalled at about 1,000,000 at the height of the Enquirer’s grisly period a few years ago, has risen to 2,600,000 and is still climbing.

So spectacular, indeed, that within a couple of years, Time, Inc. had dropped its storied Life magazine and started People. As Walls chronicled, People’s success induced more of the news media to mainstream gossip coverage, with Rupert Murdoch’s newly acquired New York Post leading the way just as Trump was beginning to make his name.

Trump thrived, planting his self-serving and often dubious gossip items freely, first in the New York City tabloids and then in national venues. “He has created no great work of art or ideas, and even as a maker or possessor of money he does not rank among the top ten, or even 50,” Time said in a 1989 cover story on Trump. “Yet at 42 he has seized a large fistful of that contemporary coin known as celebrity. There has been artfully hyped talk about his having political ambitions, worrying about nuclear proliferation, even someday running for President.”

So it was natural for Trump to turn to Pecker, his friend at the National Enquirer, for election help after he launched his presidential campaign in 2015. The relationship, as Pecker acknowledged, was “mutually beneficial.” Publishing dozens of false or much-exaggerated stories about Hillary Clinton, Ted Cruz, Marco Rubio, and Ben Carson was good for newsstand sales and would help the Trump campaign.

There was a time when Trump inflated his market value on the social scene by spreading gossip about his appeal, real or imagined, to beautiful women. In the midst of the extraordinarily intense national news coverage of his 1990 divorce from first wife Ivana Trump and marriage to second wife Marla Maples, he even floated claims to have been involved with the model Carla Bruni, who supposedly left Mick Jagger for him, and to hold the interest of actress Kim Basinger and singer Madonna at the same time. (In that case, the effort backfired when the People reporter who interviewed a Trump “spokesman” by phone later learned she’d actually been speaking to Trump himself, using the name John Miller.)

By the time Stephanie Clifford, a.k.a. Stormy Daniels, came forward looking to sell the story of her alleged tryst with Trump, the market had changed. The last thing Trump’s election campaign needed was publicity about another playboy sexcapade. He turned to his fixer, lawyer Michael Cohen, to scotch the story.

Trump’s best defense was to claim that he wasn’t aware that the fixer he used time and again to lie for him had lied once again, this time through false business records, to bail out his political campaign at a crucial time. The jury didn’t buy it; there was substantial circumstantial evidence to the contrary in addition to Cohen’s own testimony.

After relying on a bungler like Cohen, Trump is left to sigh for Roy Cohn, his guide into a world where glitz and graft collided so gloriously—1980s New York. Cohn, who made his name in the 1950s as counsel to the McCarthy hearings and prosecutor of Julius and Ethel Rosenberg for espionage, showed the young son of Brooklyn builder Fred Trump the seamier side of how to win friends and influence people.

That got them both a mention in the signature New York City political-corruption trial of the 1980s; U.S. Attorney Rudolph Giuliani prosecuted Bronx Democratic boss Stanley Friedman on federal racketeering charges over multi-million dollar payoffs to obtain a city contract. I still have 2,200 pages from the transcript of that closely watched trial, including Giuliani’s cross-examination of Friedman on November 12, 1986.

Friedman assisted Giuliani through his arrogant answer to the prosecutor’s question of whether, as a lobbyist, he’d received $10,000 for making two phone calls to push along a lease deal. He corrected Giuliani to say only one call was needed. Giuliani then made sure to get Cohn’s name before the jury; indicted four times but never convicted, he was an emblem of the sleazy, slippery political underworld that Giuliani crusaded against in those days. Under questioning, Friedman said that Cohn had recruited him into his law firm just as Friedman was finishing up as a deputy mayor in December 1977—and that in his last days in the city’s employ, he helped arrange a lucrative real-estate deal for one of Cohn’s major clients, Trump. (The heavily subsidized deal in question became the Grand Hyatt Hotel, located near Grand Central Station.)

Cohn and Trump were both known for their political wheeling and dealing, and Giuliani took advantage of that as he tried to draw an unsavory portrait of how business was done in New York City. (How Giuliani later became Trump’s lackey is another story.)

With Friedman’s conviction by a federal jury in New Haven, Connecticut, it was clear his move for a change of venue backfired; a jury of New Yorkers might have been less horrified by his cocky, self-serving way of doing business. He was sentenced to twelve years in prison for his role in turning New York City’s Parking Violations Bureau into “a cesspool of corruption,” as an appeals court put it. The evidence showed that he used his ties with the Queens borough president and Democratic boss, Donald Manes, to skew the bidding for a contract to produce the city’s first handheld parking-ticket computers. Manes and his patronage appointee in the parking bureau who skewed the process each got about one-third of the stock in the company getting the contract—the total value of the company was $22.7 million, about $65 million in today’s dollars—and Friedman got the rest. Manes committed suicide before he could be charged; the insider, Geoffrey Lindenauer, turned informant.

Would a change of venue in Trump’s Manhattan trial have made a difference? I suspect he’d have drawn the same result as Friedman did. Would it have made a difference to have another judge besides Acting State Supreme Court Justice Juan Merchan? Not if it was someone like Federal Judge Whitman Knapp, the famous investigator of New York police corruption, who remarked (outside the jury’s presence) that Friedman’s testimony was “highly improbable.”

Trump came of age treading the edges of this swamp, and it shaped him. “The dynamics that defined New York City in the 1980s stayed with Trump for decades; he often seemed frozen in time there,” as Maggie Haberman writes in her Trump biography, Confidence Man. 

When word arrived that Stormy Daniels was looking to sell her story shortly before the election, Trump turned to Michael Cohen, who was “really more of the defendant’s fixer than his lawyer,” prosecutor Joshua Steinglass said in his closing argument. “He was the buffer, the guy with the boots on the ground that could bully people and threaten them with lawsuits, all at the defendant’s [Trump’s] direction.” It sounds like a good description of Roy Cohn.

In this case, the story of Trump and Daniels was too sordid even for the National Enquirer, as Pecker testified—he was afraid that Walmart, where his magazine was distributed, would object if word got out of any deal with a porn star.

And Trump had already gone to that well twice. “I said, 'We already paid $30,000 to the doorman, we paid $150,000 to Karen McDougal, and I am not a bank,'” Pecker testified, describing earlier claims about Trump that he’d bought and buried. “If anybody was going to buy it, I thought Michael Cohen and Donald Trump should buy it.”

The ensuing paperwork for that transaction led to the first felony conviction of a former president of the United States.

At this writing, there is much speculation about the sentence Merchan will impose on July 11. Most commentary suggests that since this is Trump’s first conviction, he’s unlikely to get prison time.

I’m not so sure. Merchan might take note of presiding over the conviction of the Trump Organization in 2022 for criminal tax fraud and falsifying business records—a case in which the prosecutor accused Trump himself, though not a defendant, of sanctioning the tax fraud. Then there is the civil fraud verdict handed down in February against Trump for inflating the value of his assets—resulting, as the judge detailed in his ruling, in savings of hundreds of millions of dollars on interest payments.

The consistent thread here is cheating, whether in business or in personal life: the two mingled for Trump. Thinking back again to 1980s New York, I’m reminded that as a federal prosecutor, Giuliani persuaded judges to give prison sentences rather than the customary probation to first-time white-collar offenders for insider trading. It was, as I recall him telling me, just another form of cheating.