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 special or mysterious; they emerge as a clear consequence of his background. The book’s thesis—Trump’s gonna Trump—is pointedly unglamorous, in keeping with Haberman’s deflationary assessments of Trump’s character. Some passages unfold as groans of exhaustion: “For all the intrigue that is part of the Trump mythos,” Haberman writes, “the irony, say those who have known him for years, is that he has had only a handful of moves throughout his entire adult life.” Part of the work of “Confidence Man” is to source and taxonomize each of these moves, and to identify when Trump is drawing on any one of them. He learned showmanship from the former mayor Ed Koch, the Yankees owner George Steinbrenner, and the McCarthyite lawyer Roy Cohn—whose “singular talent,” the book notes, was for “emotional terrorism.” From the remnants of Brooklyn’s Democratic machine he extracted lessons about the power that might be gained from pitting ethnic groups against one another.
As a construction tycoon, Trump sought out unsavory accomplices, partnering on one project with a Soviet-born investor who’d been convicted for “both first-degree assault (shoving a broken margarita glass into a man’s face) and fraud (a pump-and-dump penny stock scheme involving the Genovese crime family).” He donated heavily to politicians who could grease the wheels of his business machinations. (The Police Athletic League, a cause beloved by the former Manhattan District Attorney Robert Morgenthau, profited handsomely from his shamelessness, Haberman writes.) And, early on, he figured out how to neutralize threats by hiring them, as when he lured Anthony Gliedman, the housing commissioner who denied his request for a tax break on Trump Tower, and whom Trump subsequently threatened and sued, to come work for him several years later.
The book is frank about Trump’s cruelty. It narrates how he and his siblings cut off medical funding for his brother’s infant grandson, who was born with a disorder that led to cerebral palsy, in order to punish some of his relatives during an estate dispute. And Haberman stresses the racism that has permeated Trump’s image since he and his father were sued for housing discrimination in the seventies. But she also acknowledges Trump’s seductiveness, recognizing that he “was mesmerizing to watch, his speech fast and cocky and self-assured, with the ability to be both funny and cutting, both charming and derisive, often in the same sentence.” Trump’s gestures, Haberman insisted, have a metaphysical hollowness. “A word I didn’t use in the book,” she told me, “but that a lot of people who’ve worked for [Trump] use, is ‘nihilist.’ ” In “Confidence Man,” Haberman writes that Trump “is often simply, purely opaque, permitting people to read meaning and depth into every action, no matter how empty they may be.”
During the Trump Presidency, Haberman’s output and name recognition placed her at the center of debates over how journalists should cover his Administration. “People wanted her to provide a normative framing for what was going on,” the professor and media commentator Daniel Drezner said. Instead, Haberman’s Times articles adhered to the journalistic conventions that the press critic Jay Rosen has labelled “the view from nowhere.” Rife with ostentatious neutrality, the pieces were seen to grant Trump and his circle undue legitimacy. Haberman, one of the main conduits of Oval Office drama, came under particular fire for her handling of anonymous sources. She was accused of skewing her coverage in exchange for access (a claim she rejects)—these allegations sometimes came from the same critics who bristled at her paper’s studious impartiality. As a woman and a receptacle for liberals’ disappointed hopes about the capacities of journalism in the MAGA era, Haberman received “a tremendous amount of vitriol,” Drezner said.
Haberman told me that she believed a number of people from the Trump era remain newsworthy, either because they illuminate something about Trump himself or because they are the subjects of or witnesses in investigations. Questions about her process elicited similarly guarded answers. The publication of “Confidence Man” reignited controversies over Haberman’s ethics. The media personality Keith Olbermann and the opinion columnist Michael J. Stern, among others, charged her with failing to immediately report vital knowledge uncovered over the course of her book research—most significantly, that Trump had told aides that he wasn’t leaving 1600 Pennsylvania Avenue after the election. Haberman argued that she did not learn this until after Joe Biden took office.
“I think that there’s a misunderstanding among certain aspects of our readership about what it is we do,” she said. “They’re outraged by what we’re covering, and they don’t understand why it’s not having the effect it should. So it must be that we’re doing it wrong.” I noted that the idea of silver-bullet journalism—of the one article that levels the Trump White House—is deeply bewitching. She said that this notion is “just not realistic”: in a climate of partisan absolutism, distrust of the media, and the coarsening of norms, the context around the news itself has shifted. I suggested that, once, reporters could vanish behind their facts. Today’s press culture thrusts reporters onstage, parsing their judgments and perspectives as part of a ceaseless Twitter meta-drama about journalistic integrity. Haberman countered that such soap operas have been happening for years. “People have a right to feel however they feel,” she said, dismissing the subject.
Parts of “Confidence Man” seem to wrestle with its author’s role in amplifying Trump’s lies. “The media writ large was unprepared to cover a political candidate who lied as freely as Trump did, on matters big and small,” Haberman reflects, adding that the word “lie” presumes knowledge of a speaker’s motivations. “Even those of us who had covered Trump for years struggled with how to handle the gush of falsehoods that dotted his sentences.” But, in person, Haberman appeared nonplussed when I asked how she negotiates the gray areas in which her duty to break news aligns uncomfortably with Trump’s interests. “My job,” she said, “is to provide as much information on a topic as possible that is significant and relevant and related to events.” What a President does, she noted, will always get coverage.
There is also the question of what prolonged exposure to Trump—a man who profanes and corrupts everything he touches—has done to Haberman herself. As we were talking, her phone buzzed. She glanced at it, then apologized. She said that she had never approved of anything Trump had done—evaluating him is not her job. The phone buzzed again. Further introspection on the subject of stifling her emotions did not seem to interest her, perhaps because she sees no alternative. Feeling is also not her job. She turned the phone over.
Haberman has spent a good part of the past seven years immersed in Trump’s deranged fantasia of American life. Her multitasking and compartmentalizing, which the press has covered tirelessly, almost seem like necessary steps in the quarantining of order—individual and psychic as well as shared and political—from chaos. But, for all Haberman’s reticence, she maintains a combative Twitter presence, and is quick to press her case in replies when she believes that she’s been mischaracterized. Both she and her subject navigate the public sphere as if they have something to prove. And Haberman, like Trump, knows how to spin: “Confidence Man” makes a show of refusing Trump’s enticements. In the epilogue, Haberman describes a post-Presidential interview in which Trump cracked to his aides, “I love being with her, she’s like my psychiatrist.” The next sentence reflexively brushes his statement aside, insisting, “It was a meaningless line, almost certainly intended to flatter.” Haberman’s point is that Trump rarely changes from context to context; he treats everyone like his psychiatrist. Yet her emphasis on her own unspecialness feels more canny than sincere, animated by the need to convey that she is immune to Trump’s games. It’s the gesture of a writer who knows that her unsentimental view of the President anchors her credibility.
And, for all Haberman’s success in demystifying Trump, at times she seems to vest him with eerie power. In interviews, she has often invoked the children’s book “Harold and the Purple Crayon” to illustrate Trump’s peculiar blurring of fact and fantasy. The tale concerns a boy named Harold who goes for a walk in the evening and draws things from his imagination, including an entire city, with his enchanted crayon. “What Trump tries to do,” Haberman told me, “is create realities for himself and everyone else.” But his conjuring is not—she searched for the right word—“friendly”; there’s a “malevolence” to it. Toward the end of our meeting, Haberman told me that she is superstitious. She was wearing an evil-eye bracelet. Another evil eye was in her pocket. “I just have totems,” she said, hoarsely, because her press tour had already begun and she was losing her voice. I mentioned her well-documented fear of flying. Is it the claustrophobia that bothers her? She stared. “It’s the crashing.” Trump, apparently, does not get fazed by planes: on Air Force One, Haberman said, he’d sometimes continue talking during rocky landings, while reporters slid around on their seats. Trump’s insistence on taking unnecessary flights “kind of goes to what he will sublimate in the service of something else,” Haberman said. The former President once told her that he found air travel “spooky.”
Haberman’s own sense of Trump’s spooky potency continues to shape her coverage. This past November, by the end of the candidate’s meandering, hour-long campaign announcement, she had tweeted about the speech more than twenty times. Other commentators, reacting to Rupert Murdoch’s withdrawal of support and the strong Democratic showing in the midterms, were beginning to treat Trump like a political has-been. Haberman’s assessment was grimmer. “Trump is growing visibly with his speech and delivering some adlibs,” she wrote on the site, echoing her observation, in “Confidence Man,” that in the eighties news outlets treated him “as if he were born anew with every story.” (At one point in our conversation, she told me that he “regenerates.”) As Trump’s political missteps and legal woes pile up, Haberman appears to be relaxing her vigil. In a December 19th front-page article, she portrayed the candidate as “a shrunken presence on the political landscape.” Yet, if a single overarching lesson emerges from the body of work that Haberman has assembled over the past half decade, it’s that the press and the American public discount Trump at our peril.
Rosenhas taken issue with Haberman’s characterization of Trump as a “master” of media manipulation: “If you are a man, and you bite a dog,” he wrote, “that does not make you a master of anything.” But Haberman, who tends to predict that Trump will express his worst impulses and cause maximum damage, told me she believed that he is more often underestimated than overestimated. The former President “is not what he seems,” she said, “but he’s not nothing. That’s what people have really struggled to understand.”
Articles about Haberman like to say that the mother of three, who will turn fifty this October, desperately needs a break. The profiles sometimes suggest that she is “addicted” to her job, yet it might be equally accurate to say that she is enthralled by it: she made an initial choice and then lost the agency to decide. Trump, having tasted the fairy food of the Oval Office, seems similarly stricken, entranced by power and fame that he is unable to forsake. For his first term, Haberman has said, he wanted to campaign more than he wanted to be elected; now he wants to be elected without all the travails of campaigning. As the 2024 race gears up, the Confidence Man and his chronicler have become each other’s context, bound together and propelled by desires that both are and aren’t their own. ♦
