The Undoing of Jeffrey Toobin

Until Jeffrey Toobin’s fateful appointment with Zoom on Oct. 15, his quarantine was going better than most people’s.

In August, his eighth book, “True Crimes and Misdemeanors: The Investigation of Donald Trump,” about Robert Mueller’s inquiry into election meddling, was published — getting positive reviews and a brief berth on the New York Times best-seller list. His third, about the Monica Lewinsky scandal, is being filmed by Ryan Murphy for a limited series on FX.

And over on HBO, he was about to appear as himself on the whodunit “The Undoing,” delivering commentary on the murder trial that shapes the story’s arc.

Then in a matter of minutes, Mr. Toobin, 60, committed the act that would make him subject, not observer, of scandal, investigation and commentary. While working on a podcast about the presidential election for WNYC and The New Yorker with some of the magazine’s other well-known journalists, including Jane Mayer and Masha Gessen, he was seen lowering and raising his computer camera, exposing and touching his penis, and motioning an air kiss to someone other than his colleagues, Mx. Gessen said. The magazine suspended Mr. Toobin that day and executives began an investigation.

“It wasn’t a full-out sexual act, but it was much more than a second,” Mx. Gessen said. “I was really, truly shocked.”

Four days later, Vice broke the news about the incident. New York Public Radio, the parent organization of WNYC, which in 2017 fired the broadcasters Leonard Lopate and Jonathan Schwartz after accusations of inappropriate behavior, informed employees and board members in an email that Mr. Toobin, a frequent contributor, was banned “indefinitely” from its airwaves and podcasts.

And the gavel of public opinion came banging down. Jimmy Fallon made fun of Mr. Toobin on “The Tonight Show.” Donald J. Trump Jr., whom the journalist had criticized, was among those gleefully heckling him on Twitter. So was O.J. Simpson, whose murder trial Mr. Toobin made his name covering. (“At least Pee Wee Herman was in a X-rated movie theater,” Mr. Simpson said in a video.)

Now that name was a punchline, a headline, a hashtag (#MeToobin) — and a point of debate. For as many people were excoriating Mr. Toobin for lewd and inappropriate behavior in a virtual workplace, others were thinking, or even saying, “there but for the grace of God go I,” acutely conscious of all the private or potentially embarrassing moments they’d stolen in this odd new zone where we now meet our colleagues.

The fragile boundary between screen and reality was showcased on, of all places, the cover of the Dec. 7 New Yorker, which features a woman at her computer, crisply attired above the waist; in casual disarray below.

By the time this issue was published, Mr. Toobin’s contract with the magazine had been canceled, and he had requested a leave of absence from CNN, where he is chief legal analyst, and had sometimes appeared multiple times a day. When the episode of “The Undoing” that featured him aired in late November, his image had been edited out, leaving just the audio of his fictional commentary.

His once widely heard public voice was silent throughout the confirmation of Amy Coney Barrett to the Supreme Court and during the election. He also declined to comment for this article.

‘He’s Complicated’

One of Mr. Toobin’s favorite books is “The Great Gatsby.” He has referred to its narrator, Nick Carraway, in The New Yorker, in articles written for other publications and on CNN. For a time, he attached the name to a personal Gmail account. Carraway is someone “neither all good nor all bad, not all right or all wrong, part of the story but also outside of it,” Mr. Toobin said in “By the Book” column in The New York Times in 2016. “He’s complicated.”

Mr. Toobin’s path to journalism at least, was simpler than Carraway’s to bond trading. He grew up on the Upper West Side and attended the private school Columbia Grammar & Preparatory. His father, Jerome Toobin, was the news director at Channel 13, but the family star was Jeffrey’s mother, Marlene Sanders, a correspondent for ABC and CBS News who was among the first female journalists on the ground in Vietnam.

In a 2015 interview with The Times after her death, Mr. Toobin said he was raised knowing women could be both mothers and professionals: “This was her life. She had a job and she traveled and she had a son she loved.”

She actually had two sons. Mr. Toobin’s younger brother, Mark, was born in 1967 with Down syndrome and lived away from the family, most recently in a group home in Connecticut. Mark was not mentioned in Ms. Sanders’s Times obituary.

At Harvard, Jeffrey Toobin majored in history and literature, graduating in 1982; he served as editorial chairman for The Crimson newspaper and met his future wife, Amy McIntosh.

He went on to Harvard Law School, Ms. McIntosh to Harvard Business School. They married in 1986. An assistant secretary of education in the Obama administration, she now consults. They have two adult children, Ellen, and Adam. Mr. Toobin also has a younger son, Rory, with Casey Greenfield, a lawyer.

In Mr. Toobin’s early career he clerked for a federal judge, served as an associate counsel during the Iran Contra proceedings and worked as an assistant U.S. attorney in Brooklyn. In 1991, he published his first book, “Opening Arguments: A Young Lawyer’s First Case, the United States v. Oliver North,” a Carraway-like personal account of his background role in someone else’s story.

In Washington, he’d befriended a young reporter named David Remnick, who facilitated his introduction to Tina Brown, the editor of a splashy new iteration of The New Yorker. “I really hired him on impulse, thinking I would take a risk on him,” she said. Mr. Toobin started at Talk of the Town, then became a star while covering the Simpson murder trial (resulting in the best-selling book “The Run of His Life,” also an FX series). “He could combine news sense with gravitas and he broke news again and again,” Ms. Brown said.

In the office, Mr. Toobin sat down the hall from Mr. Remnick, who won a Pulitzer Prize for his book “Lenin’s Tomb,” in 1994, and the two men became closer. Named Ms. Brown’s successor four years later, Mr. Remnick led the magazine out of a period of red ink and retained its prestige even as sister titles have receded, floundered or folded. The New Yorker has overseen coverage central to the national discourse around sexual misconduct.

Still, as Condé Nast, the publisher of The New Yorker, has, along with other media organizations, faced criticism of elitism and tardiness around diversity, there is little room for error from even its veteran VIPs.

In June, the editor of Bon Appétit, Adam Rapoport, stepped down after a picture of him in brownface surfaced on Instagram, amid complaints from staff members that people of color were not compensated or treated fairly. Anna Wintour, the editor of Vogue (and artistic director of Condé Nast), has apologized for long marginalizing people of color in its pages. In the last few years, writers started receiving contracts that contained morality clauses that allowed termination for “public disrepute, contempt, complaints or scandal.”

And the Zoom meeting was not the first time Mr. Toobin has surprised someone in the business with his sexual forwardness. The magazine journalist Lisa DePaulo said that in 2003 Mr. Toobin asked her out for New Year’s Eve, telling her he’d separated from Ms. McIntosh. A few days after accepting, she returned home to a phone message from Mr. Toobin in which, she said, he described in vulgar terms a sex act he planned on enacting with her.

“I kept the message and played it for all my friends,” she said. (One of whom corroborated her story in an interview.) Mr. Toobin later called to confirm she’d gotten his message — “usually someone takes me to dinner first,” she told him — and told her he was back together with his wife.

“I didn’t think he was a sexual predator,” Ms. DePaulo said. “I just thought he was a nice guy who was pervy. It was just like, ‘Jeffrey? Ick!’

Mr. Toobin had followed his mother to ABC News, where he served as a legal analyst before moving to CNN in 2002. As his public profile grew, his private life attracted media attention. In 2009 and 2010, Rush & Molloy, a gossip column in The New York Daily News, reported on an extramarital affair he’d started with Ms. Greenfield, then a fact checker at Glamour, another Condé Nast publication. She became pregnant in 2008.

After her son, Rory, was born in 2009, Ms. Greenfield, who went on to work in family law, sued Mr. Toobin, 13 years her senior, over child support. She declined to comment for this article.

Mr. Toobin had no contact with the new baby “by his choice,” according to a court document, until he was nine months old. Mr. Toobin now sees Rory, who was an usher at Ellen’s wedding in 2018, a few times a month.

The affair and its resolution did not diminish Mr. Toobin’s professional standing, colleagues say, nor the range of his reporting. He visited sex clubs with the political consultant Roger Stone for a 2008 profile, explored the legacy of Ruth Bader Ginsburg and reported on Hulk Hogan’s lawsuit against Gawker Media (which had written, with snark and glee, about Mr. Toobin’s entanglement with Ms. Greenfield).

But masturbation at a remotely conducted work meeting was a new order of business.

Besides inviting mockery of a magazine whose dignity and restraint has been part of its brand since the William Shawn years, it presented an urgent, if very 2020 human resources issue. “I want to assure everyone that we take workplace matters seriously,” Stan Duncan, the chief people officer of Condé Nast, wrote in a Nov. 11 email sent to the staff of the magazine, announcing that Mr. Toobin would no longer be associated with it. “We are committed to fostering an environment where everyone feels respected and upholds our standards of conduct.”

A spokesman for Condé Nast declined to comment, as did Mr. Remnick. He and Mr. Toobin have not spoken since the day of the Zoom transgression.

‘An Inappropriately Long Lunch Break’

It’s unclear if, when or how Mr. Toobin will return to public life. He is on leave from CNN, whose executives are unwilling to discuss his future. (A spokeswoman confirmed that he remains the network’s chief legal analyst but would not comment further.) Three CNN employees say that network president, Jeff Zucker, is a big fan of Mr. Toobin’s and a believer in second chances. But Mr. Zucker may be leaving CNN in 2021, making his opinion perhaps irrelevant.

Besides the FX series, Mr. Toobin has several Hollywood projects in development; it is unclear how, if at all, his fall from grace might affect these. A film version of “American Heiress,” Mr. Toobin’s book about Patty Hearst, was to star Elle Fanning but was canceled by 20th Century Fox Film in 2018. The Gawker article has been optioned by Anonymous Content, the production and management company. “The Nine,” his best-selling 2007 book about the Supreme Court, is being developed for Warner Bros. by a group led by Rob Reiner. An adaptation of “True Crimes and Misdemeanors” is also in the works.

A representative for Doubleday, Mr. Toobin’s current publisher, said that his contract had been fulfilled with that most recent title, leaving him in limbo there too. But judging from the reaction to and discussion of the now-infamous Zoom call, there would likely be a market for his own writing about it.

Several of Mr. Toobin’s longtime associates feel he was unfairly punished. “You are a fine person and a terrific journalist and did nothing here to hurt anyone outside of yourself and your family,” Jonathan Alter, a friend of Mr. Toobin’s for 40 years, tweeted after Mr. Toobin announced his exit from The New Yorker.

“I don’t like Twitter mobs, and I don’t like bullies from the left or the right taking part in cancel culture,” Mr. Alter said later by phone. “I have trouble with the conflation of offenses. I don’t put Al Franken in the same category as Harvey Weinstein.”

Ms. Brown, who worked with Mr. Weinstein for years after she left The New Yorker, agreed. “I think 27 years of superb reporting and commitment to The New Yorker should have been weighed against an incident that horribly embarrassed the magazine but mostly embarrassed himself,” she said.

Malcolm Gladwell, one of the magazine’s best known contributors, said in an interview: “I read the Condé Nast news release, and I was puzzled because I couldn’t find any intellectual justification for what they were doing. They just assumed he had done something terrible, but never told us what the terrible thing was. And my only feeling — the only way I could explain it — was that Condé Nast had taken an unexpected turn toward traditional Catholic teaching.” (Mr. Gladwell then took out his Bible and read to a reporter an allegory from Genesis 38 in which God strikes down a man for succumbing to the sin of self-gratification.)

Even Mx. Gessen, who initially found the incident “traumatic,” said they now feel sympathy for Mr. Toobin. “I think it’s tragic that a guy would get fired for really just doing something really stupid,” they said. “It is the Zoom equivalent of taking an inappropriately long lunch break, having sex during it and getting stumbled upon.”

But Mr. Toobin may not want anyone’s pity. Amid the 2018 Supreme Court confirmation process for Justice Brett Kavanaugh, the journalist scoffed on CNN at Republicans who said white men, as a demographic, were being mistreated. “Garbage,” Mr. Toobin said. “All this whining about the poor plight of white men is ridiculous.”

Alain Delaquérière contributed research.

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