“When did Donald Trump become a goon?”

What I learned from 40 years of watching our future President.

David Letterman made a rare appearance with the gals on The View last week and asked a question that has been troubling me for some time. When was it, he wanted to know, that Donald Trump stopped being able to fake actual human behavior and went totally unhinged fascist. (Actually, Dave used the word “goon” but you get the idea.)

As a demonstration that a pre-goon Trump did once exist the producers teed up a 30-year-old clip of Letterman skeptically grilling Trump about how much money he had. This was around the time that Trump was trying to persuade the editors at Forbes that he belonged on their annual 400 Richest People list. It was also about the time that Trump’s businesses began hemorrhaging money and he was well on his way to the top of the IRS’s Biggest Losers list.

In the clip, Trump declined to answer Letterman specifically although he sheepishly didn’t deny that it was a lot. What is most astonishing about the exchange is how polite, even deferential, Trump was to a guy who a) clearly didn’t believe him and b) insisted on calling him Donald in his best “Now, Donald” schoolmarm voice. The now-famous counterattacker was on this occasion at least a curiously charming young man who took the ribbing like a man with an actual sense of humor who was having fun. His responses were good-natured and contained full sentences.

So, what happened to that Trump, the kinder-gentler Donald who wanted nothing more than anything to be admired and accepted by the rich liberals who ran Manhattan’s social and political circles, lusted after by aspiring supermodels, and pronounced a stable genius by the editorial board of the New York Times?

For much of the 45 years I lived in a rent-stabilized apartment on 57th Street in Manhattan three blocks west of Trump Tower, Trump was known to most neighborhood locals as a colorful young white boy on the make who had inherited some money from his dad and liked to call up the New York Post’s Page Six gossip columnists, pretend to be his own PR man, and brag about grandiose deals that usually fell through or the latest supermodel who was just itching to get next to his own studly self. Once in a while, he might actually have met the woman in question.

The Post gossip writers knew it was Trump himself on the phone but they played along because he was good copy and was always willing to rat out someone more famous to get his own coverage.

He wasn’t the richest real estate mogul in Manhattan. He wasn’t even the twentieth richest. He had inherited a decent sum from his cheapskate father, Fred, who over many years of dubious business practices and scrupulous tax avoidance had built an empire of government-subsidized, sub-standard, low-income housing in the working class borough of Queens. For sure, that wasn’t something a young man who craved fame and attention would want to put his name on.

Trump was rich but far from being the real billionaire he liked to play in real life and being a slumlord in Queens is not the kind of branding he wanted for himself. He had bigger dreams.

Building Trump Tower

Trump’s first big chance to stamp the Trump name on a prestigious piece of Manhattan real estate came in 1978 when he was able to finance the purchase of a 50 percent stake in the iconic old Bonwit Teller department store on 56th St. and Fifth Avenue. Two years later, he was under pressure to complete the process of tearing it down and begin building what is now Trump Tower.

Although he swears he knew nothing about them being undocumented at the time, the consensus story is that young Donald stumbled across a fly-by-night contractor who was using “illegals” from Poland to do a smaller window and job-site cleaning job next door. They had never done the heavy demolition work required to remove a 12-story building in midtown Manhattan and lacked even the basic equipment to do so.

Nonetheless, Trump made the dubious contractor an offer he couldn’t refuse and from January to March 1980, the Polish workers sneaked over from the job next door and worked two shifts, one from 6 a.m. to 6 p.m., the other from 6 p.m. to 6 a.m. Some later testified that they lived on the site. When they were paid at all, they got $4 to $5 an hour, court documents show, which at the time was less than half the prevailing union wage and just above the state minimum wage of $3.10 an hour.

Still denying that he knew the workers were undocumented, Trump paid $1.4 million in 1998 to settle a class-action lawsuit that alleged he stiffed a union pension fund by employing the illegal Polish laborers to demolish the building.

But, then as now, Trump usually found a way to skate through scandals that would have wrecked most people.

Nobody ever thought New York real estate was a squeaky clean business and there was no shortage of equally loathsome players in the game when Trump came on the scene. (He wasn’t Leona Helmsley, after all) Sure, he was a liar and a tabloid bullshitter but he was friendly with (and gave money to) politicians from both parties who could do him some good. He generally could get through a social event without insulting anyone. Some people actually recall having pleasant conversations with him.

Television City was Trump’s Rosebud

So what happened to turn a relatively normal young real estate tycoon wannabe into the bitter, angry, vindictive, spiteful, insecure, obnoxious, willfully unattractive, incoherent sociopath that he is today?

From my observation perch a few blocks west of Trump Tower, I believe his descent into total darkness and soul-killing cynicism began in earnest with the collapse of his “dream project” — a plan to build a humongous commercial and residential project called Television City (he later changed the name to Trump City) on the largest undeveloped tract of land in Manhattan, the old Penn Central rail yards on the bank of the Hudson River on the upper West Side.

This was not a sudden or impulsive notion. Trump had first acquired an option on the property for $10 million (with nothing down) when the Penn Central went into bankruptcy in 1974. After a couple of his plans were rejected, the development contract was given to another group whose plan was approved by the city but they couldn’t raise the financing. Trump swept in again and bought that group’s stake for $115 million — not just an option but actual ownership.

The project was initially called Television City because NBC was threatening to leave its long-time home in Rockefeller City and move elsewhere. The city was desperately trying to persuade the company to stay so a possible favorable real estate deal was on the table.

In November of 1986, Trump unveiled his biggest and boldest plan for the property. On those 76 acres, he proposed to build nearly 8,000 apartments and condominiums for up to 20,000 people, almost 10,000 parking spots, some 3.6 million square feet of television and movie studio space, and some 2 million square feet of high-end stores. There would be six 76-story towers, and looming atop it all one skyscraper twice that height. It would be, according to Trump, the tallest building in the world. Nobody, he said, had ever seen anything like it. He, himself, would live on the top floor.

The New York Times, neither failing then nor now, actually agreed: “Unlike other driven developers, he evinces no desire to become a cultural or civic potentate. He wants to be a builder like the hero of Ayn Rand’s novel, so large that the skyline is his profile… The West Side development…is his bid for immortality.”

Resistance to the Trump plan was swift and merciless. West Side apartment dwellers, like me, who lived literally in the shadows of the proposed towers, believed we would never see the sun again. 57th Street would become Oslo at 3 p.m on December 21 year-round. City officials and community organizers demanded parks and easements and low-income housing. Public hearings were long and contentious and went on for years. The city’s byzantine maze of building regulations and mob payoffs were an endless pit. The opposition was organized and committed.

Many architects were stunned. In the Village Voice column “Dump the Trump,” Michael Sorkin wrote, “Looking at the boneheaded proposal, one wonders whether the architect even visited the site. Indeed, there is evidence that he did not. The rank of glyphs bespeaks lakeside Chicago, and the centerpiece of the scheme, the 150-story erection, Trump’s third go at the world’s tallest building…was there ever a man more preoccupied with getting it up in public?”

Perhaps. most important of all for the success or failure of the project, Trump made enemies of the two most powerful politicians in New York at the time, Mayor Ed Koch, and Congressman Jerry Nadler, who represented (and still represents) the district where Trump wanted to build his dream monster. (Yes, that’s the same Jerry Nadler, who is now chairman of the House Judiciary Committee, and Trump’s current bête noire in Washington.)

Although Trump had once given or raised $70,000 for one of Koch’s mayoral campaigns in hopes of getting him on board, the irascible mayor — perhaps encouraged by Jerry Nadler — cut the legs out of Trump’s bid by giving the tax abatement directly to NBC rather than to the developer. (NBC eventually decided to stay at Rockefeller Center.)

Trump responded to the snub by pronouncing Koch a “moron.” The mayor answered in a 1990 private essay by writing: “Donald Trump is one of the least likable people I have met during the 12 years that I served as mayor. It is incomprehensible to me that for some people he has become a folk hero.”

He endorsed an assessment of Trump’s credibility and integrity that was rendered by a former deputy mayor, Alair Townsend, who famously said: “I wouldn’t believe Donald Trump if his tongue were notarized.”

We know from the New York Times reporting on Trump’s tax statements that he was deeply buried in debt by the early 90s and had lost more money than any other taxpayer in the U.S. His Trump City vision was in tatters. He did something that he has been unwilling to do as President…compromise. He redesigned the project much more modestly with his onetime opponents, the Municipal Art Society and five other civic organizations, creating a 21-acre public park along the water and pulling the buildings back to a newly created extension of Riverside Drive.

By 1994, Chase Manhattan was demanding repayment so Trump brought in a group of Hong Kong and Chinese investors who bought the $300 million mortgage on the land for $82 million. Trump was still the public face of the deal but he no longer had the controlling interest. Jerry Nadler kept the project idling for another three years but building started in 1997 and today a much more modest community called Riverside South stands where Trump City aspired to be.

Despite two decades of bitter warfare over the fate of the project, in the end, Trump made millions of dollars and reduced his massive debt and repaid some back taxes. Today, there are actually residential buildings on the site, at least one of which — last time I checked — bears the name Trump Place.

But Trump City never happened. The one big deal that would have changed the face of the New York skyline forever and signaled the arrival of greatest New York developer ever, Robert Moses be damned. The deal that would have eclipsed Fred Trump’s empire in one giant leap.

Trump City was supposed to be his legacy. Not a bunch of failed casinos. Not a television show on which he played a billionaire chief executive. Not even four or eight years of his dotage locked up in government-paid housing in Washington watching cable TV and hurling nasty invectives at the outside world.

Over the two decades that Trump spent trying to get his Trump City vision off the ground, the narcissistic but optimistic creature with visions of greatness that was young Donald morphed into a paranoid bitter old man with a suitcase full of grudges and resentments. His smashed American dreams turned out to be not unlike those of his working class supporters. Just bigger. And just like them, he is still looking for someone else to blame.