Before Donald Trump became a master of the 140-character tweet, he carried on a vigorous, often combative campaign of correspondence with his critics through the letters-to-the-editor columns of newspapers and magazines. As a financial journalist and columnist who has spent decades writing about business and politics in New York City, I was once the object of one of Trump’s acerbic missives. Trump’s letter came in response to a column I wrote for Crain’s New York Business about his 1997 book Trump: The Art of the Comeback. In tone and substance, the letter resembled the caustic tweets he sends today—only longer. It included an ad hominem attack, suggested that a conspiracy was afoot against him, and displayed a disquieting disregard for facts. At the time, the letter was so over the top that it seemed amusing. We gladly published it, along with the subsequent response of our readers—few of whom were Trump fans.

Today, with Trump the presumptive Republican presidential nominee, his response no longer seems quite so entertaining. As the inevitability of his nomination grows, some Republicans speculate that The Donald will somehow become more presidential. He’ll evolve, they hope, into a more thoughtful, less impulsive, less malicious politician. But the Trump we see today isn’t someone who manufactured a persona as a campaign strategy. It’s who he is, was, and probably always will be.

As a young real estate developer, Trump shot to prominence quickly in the economically depressed New York of the late 1970s. He purchased the financially struggling Commodore Hotel and, with the help of a 40-year tax abatement from the city, redeveloped it into the successful Grand Hyatt. He quickly acquired a can-do reputation when, in 1986, he took over the refurbishing of Central Park’s Wollman Skating Rink. The city had wasted six years and about $12 million trying to fix up the rink; Trump finished the project in less than six months. His deal-making proliferated. He made big investments in Atlantic City casinos, purchased the Washington shuttle from Eastern Air Lines (renamed the Trump Shuttle), completed a $400 million buyout of the Plaza Hotel, and planned to build a mini-city on the West Side of Upper Manhattan.

Though he celebrated these accomplishments in 1987’s bestselling The Art of the Deal, his portfolio came unglued quickly. After his bankers became uneasy in 1990 with his $2 billion in debt and began pressuring him to sell off some of his assets, Trump signed over the shuttle and the Plaza to creditors in quick succession. He was also forced to sell his yacht—the Trump Princess—and defaulted on bond payments for his Taj Mahal casino.

Crucially, however, Trump’s bankers kept the celebrity businessman on board as a figurehead in the enterprises they were now trying to unload. He was, as one lawyer put it, worth more to them “alive than dead.” The free-spending Trump was put on a mere $450,000 monthly budget for his business and personal life. As the creditors gradually lifted the massive debt burden by selling off properties, Trump was quick to proclaim his recovery with The Art of the Comeback. Amusingly, the most provocative parts of the book didn’t concern his so-called comeback. He made news lamenting that he’d never asked Lady Di for a date before she died, and told readers that Hillary Clinton is “a wonderful woman who has handled pressure incredibly well.” (How times have changed). Sylvester Stallone, Julio Iglesias, Howard Stern, and Frank Sinatra were among the names he dropped. What little business advice that he offered—the so-called art of the comeback—included telling aspiring billionaires to be sure they always have a prenuptial agreement, to play plenty of golf (good for networking), to be paranoid, to be lucky, and always to get even.

It was hard to be critical of a book so thin, so relentlessly self-promotional, and so thoroughly not about what it proclaimed to be about. I didn’t take the book very seriously in my column, though I did note that it had great pictures. Trump was not amused by my review, and the letter he fired off opened with what has become a familiar insult: that we weren’t really worth his time. “I don’t usually respond to Crain’s New York Business, in that it is totally irrelevant.” He then observed that my many errors had nonetheless compelled him to write.

In characteristic Trump fashion, he didn’t specify any of my alleged errors, but instead headed off into a long, ugly attack on our publisher, Alair Townsend. Trump was sure that I wrote the column (lackey that I was) only at the behest of the “very ineffective” Townsend, whom Trump had tangled with numerous times during her tenure as New York’s deputy mayor for economic development. “I know Alair’s hatred for me is great because she looked so foolish while working for the city,” he wrote. Townsend had refused to hand over huge tax subsidies to Trump for his mini-city on the West Side. When Townsend’s boss, Mayor Ed Koch, backed her, Trump labeled him a “moron.” Hizzoner, never one to take an insult lying down, shot back that Trump was “squealing like a stuck pig.”

It was what Townsend subsequently said about Trump, however, that really galled him, because it came to define him in New York during the 1990s. “I wouldn’t believe Donald Trump if his tongue were notarized,” she told a reporter (off the record, she claims to this day). Leona “Queen of Mean” Helmsley liked the line so much that she later appropriated it for herself when she feuded with Trump in the New York real estate version of Dracula vs. Frankenstein.

In his letter, Trump went on to say that, contrary to my claims, the fire sale of his properties had worked out spectacularly for him. “While Mr. Malanga tries to deride me, the Plaza Hotel deal was a great one for me. I recently sold the Grand Hyatt for a huge profit. I am not a ‘local front man’ on the [West Side] project, but owner and developer of the project,” he wrote. But, Trump ignored the fact that he had bought many of these properties at premium prices in the high-flying 1980s and sold them in the depressed early 1990s market. Though he purchased the Plaza at $400 million, his creditors sold it for $350 million, according to press reports. And Securities and Exchange Commission documents showed that he had indeed transferred much of the ownership of West Side project to his creditors.

“It will be interesting to see whether Crain’s has the ethical standards to print this letter,” he concluded. The challenge was unnecessary. From the moment we received it, we couldn’t wait to get it into print.

If Trump thought that our readers—New York business executives—would be sympathetic to him, he was gravely mistaken. Most astonishing—for its frankness—was the response from Ben Berzin, Jr., a banker who had served as a workout specialist on the Trump loans. Berzin pointed out that other people at his bank had lent Trump $100 million, and he had been given the task of trying to recover some of that money. Berzin noted that, contrary to the advertising blitz around The Art of the Comeback, which suggested that Trump “diligently worked to repay his obligation,” the real estate magnate had done no such thing. It was the creditors who had unloaded his properties, in an attempt to recoup at least some of their money. Still, Berzin wasn’t surprised by Trump’s claims. He called The Donald “a master of situational ethics” who did “not seem to be able to differentiate between fact and fiction.” And he added that, unlike successful business executives, whose mission statements might revolve around “ethics” and “honesty,” Trump’s seemed based on “self-fulfillment” and “getting even.”

New York business executives had grown skeptical of Trump’s claims because they had heard this kind of stuff from him before. When the stock market crashed in late October of 1987, for instance, Trump bragged to the press that he had “sold all of his stock last month” and took no losses. But SEC filings showed that he still owned large stakes in some companies. Forbes calculated that Trump had lost $19 million on his Resorts International holdings alone. The October crash had actually been the beginning of Trump’s unraveling.

Trump has been in attack mode more or less ever since, and Twitter has simply given him a new weapon. Sometimes, it takes him a while to get around to responding, but eventually he strikes. When journalist Mark Singer penned a profile of Trump in 1997 that Trump didn’t like, he waited until the story reappeared in Singer’s 2005 book to send the author a note in all capital letters—a forerunner of today’s tweets:

mark—you are a total loser—and your book (and your writings) suck! Best wishes Donald p.s. And I hear it is selling badly.

I have to admit, when I read that, I was jealous.

Photo by Scott Olson/Getty Images


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