Maggie Haberman, the Confidence Man’s Chronicler

Among the revelations in the recently released materials from the January 6th committee was an account of a conversation that took place in May, 2022, between the former White House aide Cassidy Hutchinson and the former White House ethics attorney Stefan Passantino. Hutchinson had just finished her third deposition with the committee. Passantino, her lawyer at the time, was in a taxi with her on the way to a restaurant. According to Hutchinson, Passantino’s phone rang—it was the Times reporter Maggie Haberman. Hutchinson asked her counsel not to take the call. “I don’t want this out there,” she remembers saying. “Don’t worry,” Passantino allegedly reassured her. “Like, Maggie’s friendly to us. We’ll be fine.”

The scene underscores a question that has shadowed Haberman for the past several years. Is she, in fact, “friendly” to Trump’s people? Or is she simply good at her job—a job that requires her, at times, to win the trust of the untrustworthy? I was somewhat surprised to see that,” Haberman said when I asked her about the conversation, characterizing her call as “routine.” Shortly after Hutchinson’s deposition, she notes, the Times published a story on the January 6th committee’s progress that included the news that at least one witness was willing to testify that Trump had approved of rioters chanting “Hang Mike Pence” and that Mark Meadows, the former White House chief of staff, had burned documents in a fireplace.

Since 2015, Haberman’s career has revolved around the most untrustworthy man in national politics. The Times hired her to cover the 2016 election five months before Donald Trump declared his first Presidential campaign. As his star climbed, she served as one of his most diligent chroniclers: in 2016, her byline appeared on five hundred and ninety-nine articles; more recently, she has averaged about an article a day. Her reporting, much of it written with other Times staffers, mingled Pulitzer-winning discoveries (Trump told Russian officials that firing James Comey relieved “great pressure” on him), palace intrigue (John Kelly clashed with Corey Lewandowski), and bathetic details (Trump watching television in his bathrobe). Her tweets frequently numbered more than a hundred and forty in twenty-four hours. She was a fixture on cable news, her face framed by eyeglasses that Trump, who shares her aptitude for pithy description, accused of being “smudged.”

After Trump rose to political prominence, Haberman became a player in the theatre of the Trump era: an avatar of journalism’s promise, but also of its shortcomings. To some, she upheld the tradition that Woodward and Bernstein built; others condemned her failure to criticize Trump’s behavior more vocally. Washington, D.C.’s power players, a wider swath of whom than wishes to admit it has Haberman’s number saved, grew habituated to her presence, if not exactly thrilled by it. Portions of the electorate learned to associate her with distressing updates about the country. Meanwhile, Trump, still revelling in his defeat of Hillary Clinton, cast her as another antagonist, the embodiment of the “Failing New York Times.” She and the President invited doppelgänger comparisons: the flashy fabulist and the buttoned-down institutionalist locked in each other’s sights.

Haberman sees herself as a demystifier. Her coverage is often grounded in statements about Trump’s character—that he thrives on chaos but loves routine, or that he stirs up infighting among his cronies. When I asked her about these conceptual scoops, she corrected me: “They’re contextual scoops.” Context is key to Haberman’s project. A characteristic article, which she co-wrote in July of 2017, emphasized that Donald Trump, Jr.,’s huddle with a Kremlin-linked lawyer proved “unusual for a political campaign” but “consistent with the haphazard approach the Trump operation, and the White House, have taken in vetting people they deal with.” It was a quintessential Haberman balancing act, which underlined both the meeting’s extraordinary nature (for Washington) and the mundane pattern that it fit (for the Trumps). A reader wondering whether to be surprised by such carelessness, such corruption, gets her answer: yes and no.

Haberman was not the only reporter to see the underlying logic in the daily bedlam emanating from Washington. She was, however, one of the most relentless and consistent. Over the years, she has honed a stable interpretation of Trump, evoking not a strongman but a showman, an egomaniac with shrewd instincts and bad opinions. (One of her refrains is “I was shocked but not surprised.”) She mounts a similar argument about Trump in her recent book, “Confidence Man: The Making of Donald Trump and the Breaking of America.” The book presents Trump as a bullshit artist whose grand theme is his own greatness. Trump, Haberman writes, “was usually selling, saying whatever he had to in order to survive life in ten-minute increments.” He “was interested primarily in money, dominance, power, bullying, and himself.” In Herman Melville’s novel “The Confidence-Man,” from 1857, the title character is a shapeshifter who remakes himself in the image of others’ desires. He gives off a hint of reality TV—with his mirages, his come-ons, his brazenness, his feints—and a dash of the Devil. Haberman’s own confidence man, though overexposed, can seem similarly elusive. This book is her most sustained attempt to pin him down.

As her book tour began, in October, Haberman and I met for an interview in Washington. Haberman’s dark hair was blown out and she wore a forest-green blouse and pink lipstick. Throughout our conversation, she gave practiced, useful answers that slipped easily into anecdote, and she continually steered the topic away from herself. We discussed Trump’s romance with the media. Haberman described how delighted he was when the New York Post headlined a piece about him with a possibly erroneous quote from Marla Maples: “Best Sex I’ve Ever Had.” She would repeat versions of these same answers and stories at her book event later that evening. To cover Trump is almost definitionally to repeat yourself: it’s a cliché-ridden beat, strewn with familiar caveats and rehearsals of his rehearsals of what “people are saying.” In the book, Trump tells Haberman that he makes the same point over and over to “drum it into your beautiful brain.” Haberman told me that she does it because she has to.

“Confidence Man,” which synthesizes years of reporting on Trump and his milieu, is, in some ways, a standard-issue Trump book. We encounter all the usual suspects: Steve Bannon and Kellyanne Conway and Paul Manafort and Hope Hicks. There are briefing-room tantrums, incredulous generals, and off-color mutterings. But “Confidence Man” is among the first to seriously consider its subject’s backstory, how he sprang from the overlapping scenes of New York real estate, city government, and media celebrity. Haberman’s Trump is also the Page Six demimondaine who flashed his grin on “Sex and the City” (“Donald Trump, you just don’t get more New York than that,” Carrie mused) and the developer who perennially stiffed his contractors and enraged the Fifth Avenue élite by destroying two iconic friezes.

Part of what makes Haberman one of Trump’s foremost contextualizers is her fluency in the worlds that formed him. Born to a publicist and a newspaperman, she grew up in the kind of privileged Manhattan set that Trump spent his early days envying. As an undergraduate at Sarah Lawrence, Haberman studied creative writing and child psychology. The subjects may have primed her for the task of deciphering Trump; her classmates, she said, “talked a lot about magical thinking.” Her first job in journalism was at the Post, which sent her to crime scenes, trials, hospitals (to document V.I.P. births and plastic surgeries), and the funerals of firefighters and civic luminaries. During Rudy Giuliani’s second mayoral term, Haberman covered City Hall, a notoriously cutthroat beat. “There was a lot of duking it out,” she said. “It made me more able to take a punch.” This world—a soap opera of excess and corruption playing non-stop through the New York of the nineties—was Trump’s, too. Haberman heard rumors of colleagues fielding calls from the magnate during which he’d dangle gossip items. The tabloid playbook, which Haberman memorized and which Trump enacted, reflected a sense that journalists and subjects could feed off one another, that the whole enterprise might be boiled down to eyes and, eventually, wallets. “I was shaped by understanding what sold in a tabloid,” Haberman told me. “He was shaped by how to attract those stories.”

Haberman’s particular way of contextualizing often seems intended to puncture or undermine. In her work, Trump’s actions don’t appear…

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