One night in 2014, Gabriel Sherman ’01 attended a cocktail party at the Four Seasons in Manhattan, an event organized to celebrate Hollywood Reporter’s annual ranking of the most powerful figures in New York media. Sherman is a well-known editor at New York magazine, with a national platform to write about the intersection of American media, politics, and power, but he had other reasons for attending the party.
Three months earlier, he had released his book The Loudest Voice in the Room, a decidedly unauthorized biography of Roger Ailes, the founder, president, and CEO of Fox News. Sherman had spent three years reporting the book, interviewing more than 600 people along the way, but Ailes was not among them. With a fury bordering on obsession, Ailes had set out to quash the book, refusing to speak with Sherman and demanding that no one else associated with Fox News do so either. And that was just the beginning of the effort to undermine the book.
Ailes associates reportedly compiled a 400-page dossier on Sherman, ran negative articles about him on far-right websites, and kept tabs on his writings and social media activities. Sherman even received a death threat during the course of his reporting, though the source
of it is unknown.
Published in January 2014, The Loudest Voice in the Room received critical acclaim and spent two weeks at the top of the New York Times best-seller list. But by the night of the Hollywood Reporter party, neither Ailes nor Fox had had much to say about it. So Sherman, whose methodical reporting had so antagonized one of the most influential media figures of his generation, hit upon one more provocative idea: He would attend the cocktail party not be feted himself, but to ask Fox’s star personalities about their reactions to his book.
Sherman arrived around 7:00 p.m. Ailes, it turned out, had declined to make an appearance, but Sherman spotted Bill O’Reilly, then Fox’s top-rated host, having a conversation with the actor Alec Baldwin. When Sherman approached and asked for a reaction to the book, O’Reilly glared at him before shouting, “Drop dead, man!” For a moment, Sherman would write later, he wondered whether the famously combustible host might strike him. Instead, O’Reilly stormed away. From there, Sherman approached the Fox star Megyn Kelly. Though friendlier than O’Reilly, she made it clear that there was no way she was going to comment. “I’m sorry, but I can’t be seen talking to you,” Kelly told Sherman. “It will get me in trouble.”
The Loudest Voice in the Room has been described as a masterwork of investigative journalism, one that is often credited with helping to set in motion the series of events that resulted in Rogers Ailes’s stunning departure from Fox in 2016. Less than a year after leaving the network, Ailes was dead. He died at age 77 of complications related to a fall he suffered at his home in May.
A few days later, Sherman stood at the front of a function room in a New York hotel, conducting a gag interview with the Donald Trump impersonator Anthony Atamanuik. The event was part of Vulture Festival, a two-day series of events organized by New York’s entertainment-themed website, Vulture. In the audience were 100 or so people in their 20s and 30s, dressed in dark jeans and flannel shirts, and squeezed into a long, narrow room with wood panel walls on the third floor of the Standard, High Line hotel in New York.
Sherman, projecting a kind of ruffled erudition in his black suit and tie and glasses, was dressed for his role as the straight man to Atamanuik, who satirizes Trump on Comedy Central’s The President Show. “Well all right, let’s get down to business,” Sherman said, turning to Atamanuik, who wore a custom blond wig and special shoes that caused him to lean forward in Trumpian fashion. “This has been what many are saying has been the worst week of your presidency. Democrats are calling for your impeachment, Republicans even are deciding to walk away from you—”
“Cowards!” interjected Atamanuik.
“On Wednesday,” Sherman continued, “the Justice Department appointed former FBI director Robert Mueller as a special prosecutor. And seemingly every day there’s another jaw-dropping leak in one of the big papers. So I have to ask you, how are you feeling about things?”
“I feel so incredible,” replied Atamanuik. “First of all, Robert Mueller, this guy looks like Herman Munster, and he looks like he got the leftover skin from John Kerry’s facelift.” After a few gasps, the crowd broke into wild laughter. Sherman, who’d been leaning on a table, stood erect and looked momentarily stunned by the viciousness of the comment. He’d learned during the reporting of his book that it doesn’t take much at the moment to make some people very, very angry—a fact that had been highlighted only the day before at a memorial service for Ailes, during which his 17-year-old son had said, “I want all the people who betrayed my father to know that I’m coming after them and hell is coming with me.”
The next day, I was scheduled to meet Sherman at 1:00 p.m. for lunch at a cafeteria located in the same building as the New York headquarters. At 11:30 a.m., he sent me a text. “Let’s say 1:30,” he wrote. “Had an emergency come up this morning.”
We met in the magazine lobby and Sherman, wearing a red-and-white-checked shirt, jeans, and a blazer, led me down one floor to the cafeteria. As we waited in line, he apologized for being late. “I was filing a police report because Ailes’s kid, he made these threatening comments at the funeral, and I was getting emails from Fox sources and executives over the weekend that were like, ‘Take this very seriously.’ Obviously, people grieve in different ways but these comments were very alarming.” I remarked that he must have found these sources to be credible given the police report he’d filed. “These are people I trust, people I’ve known for years,” he said. “It’s funny, with Ailes’s death you think the story’s sort of over but even after his death, I’m still dealing with intimidation.”
Sherman, who is 38, has been at New York magazine for 10 years now, but these days you can find him everywhere. (In late July, as the print issue of this magazine was on press, news broke that Sherman was leaving New York for Vanity Fair.) You can hardly turn on the television without encountering him. He’s in high demand as a talking head on shows such as PBS’s Charlie Rose and Real Time with Bill Maher on HBO. He’s also a contributor to MSNBC and NBC News, and he’s even at work on a Showtime limited series based on his Ailes book. “Gabe is just an extraordinary reporter, one of the best I’ve worked with in my career anywhere,” said Adam Moss, the legendary editor of New York.
Sherman grew up in Westport, Connecticut, about 50 miles from New York City. He was an accomplished ski racer, and his family would spend weekends at competitions in Vermont. When he was a sophomore in high school, he enrolled at Holderness, a boarding school in New Hampshire, where he could focus on both academics and skiing. Sherman said that, by and large, he enjoyed his time at Holderness, but the experience was complex. After growing up surrounded by Jewish friends, he suddenly found himself one of just a handful of Jews at the school. “Every Sunday all the kids would go to chapel and I would go to the biology teacher’s house, with like the four other Jewish kids,” he told me. “We’d read some religious texts, but sometimes we’d just watch the Patriots games. That sense of you’re going here and they’re going there—that was an experience that made me acutely aware of where I fit into the social structure.”
Nevertheless, Sherman excelled at Holderness. James Jung ’02.5, a fellow skier and classmate at both Holderness and Middlebury, said that even in high school Sherman displayed an almost freakish memory. “We knew all these European skiers and their statistics. We could recite them,” Jung said. “I could do that because it was something that I was passionate about. But Gabe could be like that with anything.” Jung, who lives in New York today, recalled the time that he and Sherman were on the subway together. “There were these recorded safety announcements that they made every few stops,” he said, “One day Gabe started reciting them, word for word, along with the announcements. I was amazed. I was like, ‘That was a Rain Man moment right there!’ He said, ‘Yeah, that’s just how I am. I remember things.’”
Sherman’s academic work, and memory, made an impression at Middlebury, too. “Gabe stood out in terms of his achievement—he was one of the best students in the class on Soviet-Russian politics—and also I was impressed by him in other ways so I invited him to be my research assistant,” said Michael Kraus, Frederick C. Dirks Professor of Political Science. One day, when Sherman was able to summon an obscure fact off the top of his head, Kraus remarked, “‘Geeze, you’ve got a really good memory.’ His response was, ‘Well, you know, to tell you the truth, I think I have something like a photographic memory.’”
After graduating, Sherman moved to New York and considered what to do with his life. Then in 2002 he got a job helping to cover the Winter Olympics in Salt Lake City. Upon returning from Utah, Sherman landed an internship with the New York Observer, a weekly newspaper that was then well known for launching the careers of promising young journalists. In the paper’s editor at the time, the late Peter Kaplan, Sherman found his first journalism mentor. “He would tell us young reporters that the media institutions are just as fascinating as our big government institutions,” Sherman said. This was back in the early 2000s, when the New York Times was suffering through a series of scandals, such as the reporter Judith Miller’s flawed reporting in the buildup to the Iraq War. “Peter assigned me to cover that story, and he said, ‘I want you to cover the New York Times the way the New York Times would cover the State Department.’ That’s sort of how I stumbled into covering media.”
Sherman started at New York magazine in 2008. As he worked the media beat, it became increasingly clear to him that, when it came to a news organization with the power to shape the political and cultural landscape—a news organization, in other words, that deserved to be covered like the State Department—the New York Times suddenly had competition.
More and more, Sherman noticed, it was Fox News that was setting the nation’s political agenda. Fox had been instrumental in getting President George W. Bush elected and re-elected, and with its appeal to an older, whiter, more conservative audience, and its unflinching support for right-wing causes and candidates, the network was influencing not just elections, but also the way other news outlets covered politics. Despite its growing power, however, very little was known about the organization. “I came to think of Fox News as this institution that is completely opaque,” Sherman told me. “We didn’t know how it worked on the inside—who were the people? And yet, through its kind of coarseness and the extreme rhetoric they were putting out, it was shaping our political culture the way the Times used to.”
Inside those hallways, it was not a normal company. It was a cult of personality,” he said.
So at the beginning of 2011, Sherman began work on a book about Fox News that he hoped would shed light on the inner workings of the network. But the more he tried to report on the organization, the more ferocious the resistance he encountered. “I’d call someone for an interview and they’d slam down the phone,” he said. “I’d go see them and they’d say get lost. I would have sources at Fox who would only speak to me on burner phones because they thought Ailes was tapping their phones. Or they would only meet me in the back of a bodega in a random part of Times Square. I’m writing about a news network and people are acting as if I’m writing about organized crime. About a year into the reporting I was like, something’s really off here. This is a much different story than I thought I was working on.”
The story, Sherman came to realize, was not Fox News, but the man who controlled everything about it: Roger Ailes. “Inside those hallways, it was not a normal company. It was a cult of personality,” he said. “People talk about O’Reilly or Megyn Kelly, but inside that building, the center of the universe was Roger Ailes.”
In all, Sherman would wind up talking to more than 600 people for the book. His subject, however, would not be one of them. To the very end, Ailes refused to be interviewed by Sherman. But Ailes’s attempts to sabotage the book didn’t end there, as Sherman detailed in a New York piece written soon after Ailes’s death:
He implored friends and Fox News employees not to speak with me, hired private investigators to track my movements, and set up a “Black Room” surveillance operation inside Fox News to dig up dirt on me. His political operatives prepared a 400-page dossier to serve as a source text for anonymous writers to smear my reputation online, often in anti-Semitic ways. Roger Stone was tasked with keeping tabs on my reporting, and Steve Bannon published hit pieces on Breitbart about me…. So terrified was Ailes of the prospect of an unauthorized biography that he commissioned an alternative one by Rush Limbaugh’s biographer, Zev Chafets.
If all of this seems difficult to believe, Sherman himself had trouble coming to terms with the fact that it was actually happening. What possible secrets could be driving this man, a powerful member of the media establishment, to engage in such behavior? The answer to that question wouldn’t be revealed until a few years later, but what was certain as Sherman’s reporting progressed was that Ailes was willing to do just about anything to keep him from publishing his book. As Sherman pushed forward with the project, a few of his sources told him that they suspected that Ailes might be bugging his apartment. A security consultant recommended a sweep for listening devices, but came back with an estimate of $10,000. “I didn’t have the money to do that,” Sherman said. “That was so frustrating, that sense of powerlessness because Ailes has millions of dollars and I don’t, and I felt vulnerable because I couldn’t protect myself.”
Writing a book can be a lonely process under the best of circumstances. Unlike with a magazine staff, you typically don’t have a group of colleagues for editing and support. For Sherman, this sense of isolation was magnified by the effects of Ailes’s furious pushback. So he built a small team to help him. “The biggest source of support was my wife, Jennifer Stahl,” he said. “She was a fact checker at the New Yorker, and when I started to write the book, she left her job to work with me as my editor.” Also on the team was John Homans, who was then Sherman’s editor at New York and is now with Vanity Fair, as well as an editor who worked for the book’s publisher, Random House.
One night in 2012, just before Christmas, Sherman and Stahl were returning home at about 7:00 when Sherman’s cell phone rang, displaying an unlisted number. “I answered it,” Sherman said, “and all of a sudden a voice is shouting in the phone ‘I’m coming after you! You’re going after Fox, we’re gonna come get you!’” The caller went on to detail the violence he had planned for Sherman. “I was so shaken, and then he hung up. I had no number to call back, so I called the New York Police Department. The cops came and we filled out a police report, just so that it was on the public record, so that if something ever happens to me, these were the threats that were made.” Sherman and Stahl then packed their bags and left that night to stay with Stahl’s family in Pennsylvania.
In 2014, The Loudest Voice in the Room was published. The book is a testament to Sherman’s reporting prowess. While Ailes never spoke with Sherman, the biography is a detailed, nuanced, and even empathetic portrait of its subject. Though fundamentally evenhanded, the book persuasively presents Ailes as a troubled man who saw himself and his country as under siege.
Perhaps more damaging, it demonstrates that far from fair and balanced, Fox News is in many ways a projection of Ailes’s paranoid worldview. “Gabe did more than anyone else to change the public understanding of that institution, and to show the world who Ailes was,” Homans told me.
If Sherman had any regrets about the book it was his inability to document the sexual harassment at Fox that would eventually lead to Ailes leaving the network. The book did include on-the-record accounts of women claiming that Ailes had asked them to trade sex for professional advancement, but those accusations were from before his time at Fox. “Sources told me the behavior continued at Fox,” Sherman said, “but no one was willing to go on the record to speak about it. I hoped the publication of my book might spur women to come forward. In the end, it took Gretchen Carlson filing a lawsuit two and a half years later to open the floodgates.”
In July 2016 Carlson, a Fox personality, filed her suit alleging that Ailes had sexually harassed her. A few days later, Sherman wrote an article for New York detailing the stories of six other women accusing Ailes of harassment and demanding sex for jobs and promotions. Less than two weeks after that, Sherman attended the Republican National Convention in Cleveland.
“I had Fox employees and former employees coming up to me, sobbing about their experiences with Ailes and how he abused them and made them trade sex for promotions,” he told me. “I just felt tremendous anger because he shouldn’t have been able to get away with that. I remember flying home from Cleveland after the convention. This was right after Ailes was fired from Fox. I remember sitting in the plane and tears just streaming down my face. It all was hitting me, what a monster this guy was, and he could just get away with it for so long. And I’m not an emotional guy. That was like, ‘Holy shit, this really affected me on a deep level.’”
Roger Ailes is dead now, of course. What his passing means for his alleged victims—an opportunity for closure? A denial of it?—is a deeply personal question. What’s for certain, though, is that without his guidance, the news organization he founded is in trouble. Ratings have plummeted, stars such as Billy O’Reilly and Megyn Kelly have departed, and according to Sherman, morale is suffering. “I think there’s a big kind of existential question of what happens to Fox now that Ailes is gone,” he said.
Homans told me that, to one degree or another, Sherman’s reporting helped bring us to this moment. “It’s rare to have a writer play such a role in the downfall of a major institution like that,” he said. Sherman is justifiably proud of his work, but he sounds more wistful than triumphant when he talks of Ailes’s tumble. “As a reporter, you get a very strange relationship with your subject,” he told me. “He’s someone you think about every day. And as much as I could feel angry at Ailes for all the damage he’s done, he was also someone that, in a weird way, I cared about.”
Recalling his days at Holderness School, I asked him whether the feeling of difference, so lonely at the time, had shaped him in some way. “I’m a generally happy person,” he replied, “but I think it’s part of human nature that if you’re on the outside looking in, you always wonder what that’s like on the other side of the glass.” Could being on the other side of the glass have been the very thing that gave him the perspective to pursue the biggest story of his career? “I’ve always been a bit of an outsider, just by nature,” he said. “So maybe it allows me to see things other people don’t see or don’t want to see.”
Sherman hasn’t moved on just yet from Ailes. There’s the limited series based on his book that he and Stahl are writing for Showtime, and there’s also the fact that, once you’ve been the victim of an organized smear campaign, or a death threat, you never quite forget it. During a recent appearance on Bill Maher’s show, for instance, Sherman became visibly uncomfortable when Maher made an incest joke about Trump and his daughter Ivanka. “What was going through my mind was that suddenly I was going to get sucked into some right-wing fire-Gabe-Sherman campaign,” he said. “So when Maher did that with Ivanka, through my mind I could just flash the Twitter mob coming after me. I think my strategy on stage was just to not engage with it and just keep my head down and let it pass. People have said crazy shit about me on the Internet. So, yeah, you remember that.”
Sherman brightened suddenly and a look of relief spread across his face. In July, he said, he and Stahl are expecting their first child. “It reminds you that life goes on and the world is much bigger than Roger Ailes,” he said. “Sometimes it doesn’t feel that way but it is.”