Inside Donald Trump's long, rocky relationship with the New York Times

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On January 28, 1973, the New York Times ran an article titled “A Builder Looks Back and Moves Forward,” about a New York property developer who was looking to enter the Manhattan real estate market. This builder had plenty of investments in Brooklyn, Queens and Staten Island but was unfamiliar to most New Yorkers, despite owning 39 apartment complexes in the city valued at a combined $150 million. The article also introduced the developer’s 26-year-old son, who’d been with his father’s business for five years. The father told the Times that his son “is the smartest person” he knows and that “everything he touches turns to gold."

The son, of course, was Donald J. Trump.

That Times story, about Donald’s father Fred Trump, was one of the New York media world’s first introductions to the man who would one day come to embody a certain variety of New York swagger for the world. New York City is where Donald Trump made his money, but it’s also where he honed his mastery of the media, and established his character as a brash, filterless tycoon — a persona that would later captivate the American public and fuel his 2016 presidential campaign.


Throughout Trump’s ascent from local curiosity to worldwide phenomenon, there has been no publication whose approval Trump seems to covet more than the Times. These days, Trump is—at least publicly—a Times-hater. He has tweeted that he was happy to hear “how badly the @nytimes is doing,” criticized them for covering him “so inaccurately,” and called Times columnist David Brooks a “clown with no awareness of the world around him.”

Recently, Trump unleashed a series of anti-Times tweets, following the paper’s recent front-page story on his multi-decade history of sexist behavior toward women:


Dean Baquet, the current executive editor of the Times, told Fusion that these days, the relationship between Trump and the paper is distant. “I have no particular relationship with the candidate,” Baquet said. “I've met him twice. I think his people have called to complain a couple of times. But they are always cordial.” In February, BuzzFeed reported that Trump had met with Baquet and other Times staffers as part of an off-the-record editorial board meeting. A spokeswoman for the Times said that while the Times politics team was in regular contact with the Trump campaign, "Dean Baquet and Donald Trump do not correspond about New York Times coverage or anything else."


Asked about Trump’s current relationship with the Times, Hope Hicks, a Trump spokeswoman, said, “I would refer to Mr. Trump’s Twitter account.”

But Trump’s recent criticism of the Times should be read in the context of a vast, multi-decade relationship, which has had its share of ups and downs.


Recently, during a visit to the New York Public Library’s Manuscripts and Archives Division, we discovered correspondence between Trump and executives of the Times dating back more than 35 years. Some of the Times letters were the kind of angry riposte we’ve come to expect from Trump. But more were respectful, even gushing—the private correspondence of a powerful man hoping to secure the approval of the gatekeepers to New York respectability. In one characteristic letter, Trump wrote to then-Times publisher Arthur Ochs Sulzberger that “my always high regard for ‘The New York Times’ remains steadfastly unchanged.”

This correspondence demonstrates that contrary to what readers of his tweets might think, Trump’s relationship to the Times has been one of both attraction and repulsion, and has veered between flattery and mockery, as the paper has served a role as both instrument of and obstacle to his ambitions.


1980: Donald Trump sent a letter to Arthur Ochs Sulzberger to complain about some news coverage, then retracted his complaint

Between June 6 and June 9, 1980, the Times published a series of articles about the demolition of the Bonwit Teller Building on Fifth Avenue, and Trump’s decision to destroy the two-stone bas relief sculpture on the building’s façade as part of the demolition, which he oversaw as the developer of the property.


The Times reported that the sculpture was coveted by the Metropolitan Museum of Art, and Trump had agreed to give it to the museum if “the cost of removing them did not prove prohibitive.” (In the end, Trump decided that the cost was too daunting, and the sculpture came down.) The Times quoted individuals who weren’t happy with Trump’s decision, and the negative coverage prompted Trump to write a letter to Sulzberger.

Addressing Sulzberger by his nickname, “Punch,” Trump complained that the Times had hurt his reputation with their reporting on the Bonwit Teller demolition. Trump appeared to be aware of a follow-up article that was going to be written about him by two Times reporters, Leslie Maitland and Howard Blum, and he made the following pre-emptive complaint:

…Leslie Maitland and Howard Blum, are going around, interviewing various people who have done business with us. It is, obviously, not their intention to write a positive story. The interviews, and more pointedly, a negatively written story on top of the recent negative stories, will literally make it impossible to continue my efforts in helping to rebuild New York City….and everyone is admitting that nobody has done more over the last five years.

I would very much appreciate meeting with you in order to explain my point of view. New York City is a difficult place to do business, but when you do positive things, things which no one else would have done, it truly becomes a hardship and the incentive to work in such an environment is lost.


The article, by Blum, came out on August 26, 1980 and was titled “The Development of a Developer: Donald Trump Changing Manhattan Skyline.” Blum hinted about Trump maneuvering his connections to get the deals he wanted, and cited a “sweetheart contract” that was awarded to Trump by the MTA to operate a tennis club in Grand Central Terminal. (The MTA had received a higher bid and rejected it.) On the whole, the article was largely complimentary.

On August 29, 1980, Trump retracted his misgivings and wrote to Sulzberger:

Needless to say, the recent article which appeared in “The New York Times”, as written by Howard Blum with Leslie Maitland, was fair and objective. My original misgivings, as detailed in the letter to you, were totally unfounded and my always high regard for “The New York Times” remains steadfastly unchanged.


It’s not known if Trump ever got his coveted meeting with Sulzberger.

1983: A Trump employee was rude to Abe Rosenthal, and he complained to Trump

Trump’s relationship with the Times wasn’t just business. He also had a personal relationship with Abe Rosenthal, the paper’s executive editor from 1977 to 1988. Trump attended Rosenthal’s 1987 wedding to Shirley Lord, and happily posed for the paparazzi.

This image was removed due to legal reasons.

Letters between Trump and Rosenthal found in the NYPL’s archives indicate that the two did occasionally meet in social settings, and that Rosenthal occasionally visited the Trump Tower. One day, after being treated impolitely by a Trump Tower employee, Rosenthal wrote to Trump to complain, in a letter dated November 28, 1983:

I was there on Saturday afternoon just wandering around gawking like thousands of others, and enjoying the beauty and excitment [sic] of it all. I took the escalator to the first floor, and at the landing there was really an impossibly unpleasant man directing traffic. Admittedly it was a crowded day, but that’s why he was there. His “move it along” snarls reminded me a little bit of what a guard must be like at Attica. When it came to my turn to be snarled at, I stopped for an instant and said, quite quietly, “Politely, politely, if you don’t mind.” I got some more snarls and some comment that it was I who was being impolite for bothering him.


Trump wrote back to Rosenthal and apologized, in a letter dated December 2, 1983:

…I must apologize for the rudeness of a part-time employee who obviously became carried away with his own importance. The crowds at Trump Tower have become so large that we have been forced to augment our normal staff; this is no excuse for rudeness, however, which will not happen to anyone who visits Trump Tower again.


Trump proceeded to say that he was looking forward to having lunch or dinner with Rosenthal. In his letter, Rosenthal suggested they arrange to meet “just to chat about nothing in particular.”

1984: Trump pre-empts his New York Times Magazine cover story

Just as he is quick to condemn negative coverage, Trump is equally quick to lavish praise when he approves of the coverage (or assumes that it will be positive).


Two days before a New York Times Magazine cover story about Trump was published, on April 6, 1984, Trump sent a complimentary letter to Rosenthal at the Times, expressing gratitude for the story. (It’s not clear whether Trump had been provided with advance copy of the magazine, or had simply guessed that the profile would be positive, based on the reporting he’d witnessed.) Trump wrote:

I have tremendous admiration for you and the incredible manner in which you conduct yourself and that great institution known as the NEW YORK TIMES. There is no more lasting success than what you have achieved.


The magazine’s story, titled “The Expanding Empire of Donald Trump” by William E. Geist, profiled Trump in exuberant terms. Geist described spending the day with Trump as “exhilarating,” mentioned an employee who says he proudly tells his friends that he works in the Trump building, and praised Trump’s negotiating skills and “finesse” with the zoning code. In addition, he complimented Trump’s then-wife, Ivana Trump, for retaining her “model’s figure” at 35, and wrote:

Donald J. Trump is the man of the hour. Turn on the television or open a newspaper almost any day of the week and there he is, snatching some star from the National Football League, announcing some preposterously lavish project he wants to build. Public-relations firms call him, offering to handle his account for nothing, so that they might take credit for the torrential hoopla.

He has no public-relations agent. His competitors wonder how this can be, but watching him at the sports forum provided an explanation. While executives of the other teams told the audience about problems of negotiation and arbitration, about dirty restrooms inside their arenas and street crime outside and about 'attempting to move the Mets in the right direction,' Donald Trump was electrifying the room the rat-a-tat-tat revelations, dropping names of star N.F.L. players and coaches he would sign in a matter of hours. He said further that he would 'continue to create chaos' for the N.F.L. and, by the way, that he planned to build a domed stadium in New York.


1985: Trump was called “slumlord” in an article, and Trump wrote a letter to Rosenthal calling that writer “dishonorable,” but told Rosenthal he still respected the Times

Today, when Trump insults a journalist, it is often accompanied by criticism of the journalist’s publication. But in his 1985 correspondence, Trump separated reporters from their workplaces.


On March 9, 1985, Sydney H. Schanberg of the Times referred to Trump as a “slumlord.” According to the article, Trump allegedly attempted to force out some tenants of his property at 100 Central Park South, using tactics which include “threats of imminent demolition” and ”instructing employees to obtain information about the private lives (and) sex habits of the tenants.” Schanberg accused Trump of preying on the largely elderly population, most of whom live on fixed incomes like Social Security.

In a letter to Sulzberger dated April 15, 1985, Trump called Schanberg’s writing “dishonorable.” He did however, continue to praise the Times for having “tremendously high standards” and told Sulzberger that he was writing to him as a man Trump greatly likes and respect. (In unusually self-deprecating fashion, Trump also referred to himself as a “nothing more than a frustrated writer of little talent.”)


For the next three decades, Trump’s relationship to the Times seemed to follow somewhat predictable patterns. Whenever the Times wrote something positive about Trump, a handwritten letter to the writer, editor, or publisher, filled with compliments, followed soon after. A negative piece, or something Trump deemed unfair? Complaints were sent to the very top.


On September 17, 1995, the Times published an op-ed written by Trump, titled “What My Ego Wants, My Ego Gets.” The op-ed was a response to a story that the Times had published a week earlier about Chicago financier Sam Zell’s bid for the Rockefeller center. The author of the article, Stephanie Strom, commented that Zell was possibly driven by his ego, “succumbing to the folly that lured Donald J. Trump [to buy] the Plaza hotel.” (This was the only mention of Trump in the 2,409-word article)

Trump’s response began with his initial anger at the mention of his “trophy” purchase of the Plaza, but then he went on to justify why “ego” purchases were smart business decisions, stating:

I have made far more money by allowing my ego to rule my instincts than I ever would have by figuring the bottom line alone. If you can build or create the ego value in a property from scratch, as I did with Trump Tower and almost all of my other projects, there is far more money to be made than from purchasing something that through the years has established its own value or pedigree, which can only be increased from that point.


Forbes reported that Trump bragged about being in “demand as a writer” after the op-ed was published. Trump told Forbes, “The Times got such a tremendous response from my last piece about ego, that they called to sign me up again.” Forbes reported that eyewitness said otherwise, and that Trump’s employees “begged for space for their boss.”

Then there was the infamous lawsuit of 2006, in which Timothy O’Brien, then a Times reporter, was sued by Trump for libel. O’Brien had just published TrumpNation:The Art Of Being The Donald, a book in which he wrote that Trump was worth between $150 million to $250 million, a claim based on three sources who were close to Trump. Trump claimed he was worth between $5 to $6 billion, and that as a result O’Brien’s statement were defamatory and hurt his reputation. The lawsuit was dismissed, Trump appealed, and the lawsuit was dismissed again in 2011. The courts stated that Trump hadn’t shown a “clear and convincing” evidence to establish that O’Brien maliciously published the statement with reckless disregard for facts, or with the knowledge that it was false, a requirement of libel.


The Times was not a party to the case (the publisher of “TrumpNation” was Warner Books), although the New York Observer reported that Arthur Sulzberger Jr., the Times’ publisher, was required to testify.

After last weekend’s A1 story about Trump’s behavior toward women, it’s unlikely that Trump and the Times are headed for a short-term reconciliation. But if history has taught us anything, it’s that Trump’s respect for the Times as an institution can survive occasional volatility.


Recently, during a CBS interview, Times executive editor Dean Baquet explained Trump’s compartmentalized thinking about the Times:

On the one hand, he’s a New York figure, and like a lot of New York figures he trashes the New York Times in public, but he is deeply respectful of the New York Times in private.


Trump’s old letters to Sulzberger and Rosenthal confirm Baquet’s hunches. He may call the Times a failing paper publicly, but his private correspondence suggests that at a deeper level, he continues to value the paper of record as, if nothing else, a barometer of his power.

Anisa is a New-York based, Indonesian-born, New Zealand-raised journalist who's lived in seven different countries. She writes about everything and anything that's likely to intrigue people.

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