Donald Trump and The New York Times: An abusive love story

This is not a love story with a happy ending.

No, this is a story of unrequited romance, of the bitter sting of betrayal, of heartbreak and public humiliation. It's the story of that person we all know who just can't stop crawling back over and over again.

This is the story of Donald Trump and The New York Times.

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Trump has publicly confessed his addiction to the media and sworn off CNN and Morning Joe more times than one can reasonably count. He has declared the press to be the "enemy of the people" and put reporters from Pulitzer Prize-winning institutions on blacklists, forbidden from covering his campaign events.

But the organization Trump can't seem to quit also happens to be his hometown paper — perhaps the most respected journalistic institution of all.

“The only thing that torments him is the disapproval of The New York Times," said Trump biographer Michael D'Antonio. "Every story that is critical of him hurts.”

"There is no paper that captures Trump's imagination more than The New York Times, except possibly the New York Post," said Maggie Haberman, the paper's White House correspondent. "But the Times to him represents Manhattan elites whose approval he has wanted for decades."

Trump's love affair with the Grey Lady dates back to his youth, when the island of Manhattan had not yet become home. In a powerful piece addressing Trump during the presidential campaign last year, Garrison Keillor hit the nail on the head: "The New York Times treats you like the village idiot," he told Trump. "This is painful for a Queens boy trying to win respect in Manhattan where the Times is the Supreme Liberal Jewish Anglican Arbiter of Who Has The Smarts and What Goes Where."

Keillor continued: "To the Times, Queens is Cleveland. Bush league. You are Queens."

The first time Trump's name appeared in the paper, he was 27, and the headline blared: "Major Landlord Accused of Antiblack Bias in City." It was 1973; a baby-faced Trump insisted that the federal charges that he and his father had "refused to rent or negotiate rentals 'because of race and color'" were "absolutely ridiculous." Those were his first words printed in the paper of record.

By 1976, the Times allowed Trump a more favorable light. In a profile of the golden-haired real estate mogul, the Times effused: "He is tall, lean, and blond, with dazzling white teeth, and he looks ever so much like Robert Redford. He rides around town in a chauffeured silver Cadillac with his initials, DJT, on the plates. He dates slinky fashion models, belongs to the most elegant clubs and, at only 30 years of age, estimates that he is worth 'more than $200 million.'"

Donald Trump had made it.

The paper had always occupied a venerated place in Trump's mind, but it had blossomed into an obsession by the 1980s. "If I take a full-page ad in The New York Times to publicize a project, it might cost $40,000, and in any case, people tend to be skeptical about advertising," Trump wrote in The Art of the Deal. "But if The New York Times writes even a moderately positive one-column story about one of my deals, it doesn't cost me anything, and it's worth a lot more than $40,000."

Trump added in a moment of startling honesty: "The funny thing is that even a critical story, which may be hurtful personally, can be very valuable to your business."

By the time Trump announced he was running for president in 2015, the personal hurt he had identified in the '80s was a familiar burn, but no less easy to bear. "Donald Trump, Pushing Someone Rich, Offers Himself" read the Times' headline on the day he announced his candidacy. Then came the blistering first paragraph:

In less than six months, Trump would slam The New York Times as "failing" for the first time:

By May 2016, it had become a fixation. On one particularly bad day, Trump tweeted at the Times no fewer than nine times. He has publicly called the paper "failing" in at least 55 separate tweets. "Every story is bad," Trump grieved at a rally in Columbus, Ohio. "Sometimes I'll say, 'Oh, great, this was so good, I'm going to have a great story tomorrow in The New York Times.' You know, they'll call. Always turns out to be a disaster. It's so dishonest."

But behind the scenes, Trump was unable to give the Times up. His particular loathing and fascination was linked to two of the paper's reporters, Maureen Dowd and Maggie Haberman, who offered readers frank and often unflattering portraits of the Republican candidate. "Donald Trump is mad at me," Dowd wrote last July, sounding ever so much like an unmoved girlfriend whose ex won't stop texting her. "He thinks I've treated him 'very badly.' But he returned my call on Friday night on his way to a rally in Colorado and agreed to do a lightning round on the Democratic convention."

Dowd has even fired warning shots at the president in the form of open letters published in the Sunday Review section. From March 2017:

But no one affects Trump quite like Haberman. "She's always going to have a special place with the president," Trump's former campaign aide, Sam Nunberg, told CNN Money. "She's one of the most influential political reporters, and it's The New York Times. It may be 'the failing New York Times,' but it's also the crown jewel, and he loves it."

Occasionally, Trump's spats with the paper of record would play out in public. In August, Trump shared a report by the Times and slammed the publication for "bias" in the span of minutes:

And by November, Trump had flipped-flopped on a meeting with The New York Times so quickly and vehemently that it gave observers whiplash:

Times reporters were dizzied. "Though one of his splenetic tweets just seven hours before our meeting had again branded the Times a 'failing' news organization, he said to our faces that we weren't just a 'great, great American jewel' but a 'world jewel,'" said Frank Bruni, who also recalled Trump approaching him at a meeting in the Times building in New York and saying: "I'm going to get you to write some good stuff about me."

Added Bruni: "Winning the most powerful office in the world did nothing to diminish [Trump's] epic ache for adoration or outsize need to tell everyone how much he deserves it."

Bruni hits on an important point. In many ways, our 70-year-old president is still not so different from the boy from Queens that Keillor addressed in his piece last year. It may be 44 years since Trump's name first appeared in the paper, but you know what they say about getting over your first love — you don't.

"My friends and enemies are all in New York City," Trump told the Times in 1976. Sometimes, they're one and the same.