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I used to think the funniest thing I’d ever heard Donald Trump say was when, one day in his office, he handed me a two-page unaudited personal financial statement and said, “I’ve never shown this to a reporter before.” I knew this could not possibly be true, just as I knew that his alleged net worth ($2.25 billion) was fictitious. He could have equally credibly assured me that he’d negotiated an option to buy Canada. The only thing that might have amused me more would have been if he’d offered me the certified scorecards from when he played golf alone.

Then, as now, I never cared how much Trump said he was “worth.” I remain confident that a true appraisal would be a fraction of whatever figure he claims on a given day. His main selling point as a presidential candidate, of course, is that he’s a super-genius incredibly successful dealmaker who will make fabulous fantastic deals that will have every citizen’s head spinning—a refreshing contrast to the serially “disastrous” deals of his Oval Office predecessors. “I’m really rich,” Trump likes to say. Or the long form: “Part of the beauty of me is that I am very rich.” (As ever, in the eye of the beholder.)

In the early nineties, Trump stiffed his creditors for eight-hundred million dollars, give or take. Later, whenever this fact was mentioned, he reflexively insisted that it had never happened. Except that it had, and subsequently no one with a lick of sense was willing to lend him fresh money. Gail Collins, of The New York Times, once referred to him as a “financially embattled thousandaire.” Trump sent her a copy of one of her columns with, across her photograph, the chivalrous scrawl “The Face of a Dog!” In 2005, Timothy O’Brien, then a Times colleague of Collins, published a book, TrumpNation: The Art of Being The Donald, in which he estimated Trump’s net worth at $150 million to $250 million. Not unpredictably, Trump sued for $5 billion, alleging that this lowball calculation constituted libel and defamation. The case was dismissed four years later, after Trump acknowledged during a deposition: “My net worth fluctuates, and it goes up and down with markets and with attitudes and with feelings, even my own feelings … and that can change rapidly from day to day.”

Given that O’Brien later stated, “My lawyers stripped the bark off of him,” I admit it’s awfully Trumpish of me to claim credit for his salutary outcome. Nevertheless I must mention that, early in the proceedings, I wrote a short piece in The New Yorker advising O’Brien to string Trump along rather than immediately cutting him a ten-figure check. I confessed my envy and, in an open letter of sorts to Trump, begged him to try to make my life miserable, too: “Please, Donald… Once and for all, sue me. I need the aggravation. Not to mention the royalties.” For a change, I didn’t hear back. I’m guessing his subscription had expired.

The sage observation that “I wouldn’t believe Donald Trump if his tongue were notarized”—courtesy of Alair Townsend, a former deputy mayor of New York City—offered a simple enough rule to live by, and it’s never gone out of fashion. A healthy democracy depends, I suppose, upon the vigilance of a free press whose members feel personally affronted by the brazen mendacity of the powerful. I’m just not that touchy. With Trump, I always knew that it wasn’t my intelligence per se that was being insulted by the transparent distortions that burbled from his lips; that was just the way the man talked. I feel confident that Trump never budged from his initial estimation of me as a hapless schmuck. Still, given his campaign-trail pronouncements about the press—“scum … terrible … lying disgusting people … I hate some of these people, I hate ’em”—I’d say we got along swell. As long as he kept talking, what could go wrong? Unless Trump was having an off day megalomania-wise, he was never not good copy. Before he lifted his eyes to the horizon and decided the moment was ripe to take over the entire world, the hometown press dreaded the prospect that he might freeze us out. How would we feed our families?

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The ascendant Trump familiar to New Yorkers during the ’70s, ’80s, and ’90s was hardly harmless. He possessed a talent for inducing targeted outrage—the hair-trigger litigiousness helped—among public officials, real-estate competitors, business partners, casino shareholders and bondholders, and tenants in buildings that bore his name. He called Ed Koch, a three-term mayor, a “moron.” He said, “The city under Ed Koch is a disaster.” (Sound familiar?) Koch returned the favor with “greedy, greedy, greedy”—if Trump was “squealing like a stuck pig, I must have done something right.” Still, the damage in those days was relatively localized. Whatever games Trump was playing, the spoils in retrospect seem quaintly small-potatoes.

In 1975, when Trump was pursuing his first major Manhattan real-estate venture, the Grand Hyatt New York, on the site of the old Commodore Hotel, the then-mayor, Abe Beame, was a Brooklyn Democratic-machine-bred career civil servant—i.e., a malleable hack—susceptible to the blandishments of Trump’s Brooklyn-clubhouse-wired father and loan guarantor. Donald the dauphin presumed the license to write his own rules, and it worked. He squeezed unprecedented tax abatements from a functionally bankrupt municipal government. The monster rose from the laboratory table and walked.

During the demolition to clear the Fifth Avenue site for Trump Tower, five years later, he approved the destruction of a pair of massive limestone art-deco bas-relief panels above the entrance to the erstwhile Bonwit Teller department store. Trump had promised to donate the panels to the Metropolitan Museum of Art but later decided that properly removing them was too expensive and time-consuming. He wanted his building built. Shrewdly, he had covered his ass with a made-to-order fall guy—an in-over-his-head demolition contractor who, as it happened, employed a wrecking crew of grossly underpaid, mistreated, distinctly undocumented Polish laborers. (So much for securing the borders.)

Wollman Rink, a public ice rink in Central Park, had closed for repairs that same year. Six years and more than twelve million dollars later, it still hadn’t reopened. Trump Tower’s first tenants had long since settled in. Thus was launched Trump’s first great public-relations coup: completing the rink renovation in three and a half months, for two million two hundred fifty thousand dollars. The following year, at the invitation of a Republican activist in southern New Hampshire, he emerged from a sporty black helicopter to deliver a Rotary Club speech. Among the locals who greeted him, some held signs that said trump in ’88 and vote for an en-TRUMP-eneur. A few months later, after a television appearance, he received a Dear Donald note from Richard Nixon: “I did not see the program, but Mrs. Nixon told me that you were great … As you can imagine, she is an expert on politics and she predicts that whenever you decide to run for office you will be a winner!”

Thanks, Dick.

Next came a Kabuki theater press tour of the underbelly of the temporarily out-of-commission Williamsburg Bridge. Trump had enlisted a senior transportation official in the Reagan administration as a prop, under the pretext that Trump was just the fellow to overhaul the entire city’s crumbling infrastructure.

Because bankruptcy tribulations and domestic disarray soon got in the way, 1988 would be the last presidential year for a while in which he would contrive a Trump for Emperor charade. He was back at it in 2000 and 2004, and in 2012 he performed an especially ostentatious Prince of Denmark routine before bowing out. That he possessed no core beliefs, no describable political philosophy, and not an iota of curiosity about the practicalities of policy and governance was irrelevant—to Trump, anyway—and seemed not to factor in the decision. He had been variously a Democrat, a Republican, an Independent, and a possible candidate for the Reform Party. His intrinsic loyalty? In business, politics, and life he had remained faithful to only one constituent. And a single theme: Trump. Me. Look.

Until June 16, 2015, when he descended the escalator in the Trump Tower atrium and, with paid actors wearing Make America great again! T-shirts cheering him on, inaugurated his courageous effort to make Mexican synonymous with rapist and drug smuggler, I never thought he’d take the leap.