The Shady Side Of Jeffrey Toobin

"Jeffrey Toobin, chief legal analyst for CNN and a staff writer for The New Yorker, is one of the most recognized and admired legal journalists in the country," Toobin's profile on CNN, the network he joined 2002, reads. A graduate of Harvard Law School, Toobin served as an assistant U.S. attorney before becoming a media legal analyst and author of such best-sellers as The Run of His Life: The People v. O.J. Simpson and The Oath: The Obama White House and the Supreme Court.

Toobin rose to fame by offering his legal analysis on some of the most high-profile cases in recent history, including the O.J Simpson trialKenneth Starr's investigation of President Bill Clinton, and Michael Jackson's molestation trial. Since 2015, he's been a familiar face on CNN discussing all things Donald Trump.

But despite his impeccable, professional reputation in front of the camera, behind the scenes is a little more muddy. Approach the bench and let's have a sidebar on the shady side of Jeffrey Toobin.

Is Jeffrey Toobin really friends with Justice Elena Kagan?

In 2010, then-President Barack Obama nominated Elena Kagan to the Supreme Court while she was serving her term as Solicitor General of the United States. Jeffrey Toobin, who attended Harvard at the same time as Kagan, praised the pick in a column in The New Yorker. He claimed they were "introduced by a mutual friend," "worked together for the entire year" in a study group, and that he was the "unofficial campaign manager" for Kagan "when she ran for she ran for president of the law review."

Toobin also claimed Kagan attended his 1986 wedding, and that he visited Kagan's family after her mother died. "We are old friends. So my initial reaction to her nomination is a simple one: happiness for her," he wrote. "As I cover her nomination, and, if she is confirmed (as she likely will be) her career on the Court, readers should know this history and decide what difference, if any, it makes. For starters, from now on, I'll be calling her Kagan, not Elena."

However, a source told Page Six that Kagan barely knows Toobin. "They were only in study groups together. They weren't friends. Yet he now goes on TV every night yammering on about her," the source said. In response to Toobin's claim that Kagan "kept to herself," the source replied, "All of her actual friends say the opposite."

Jeffrey Toobin had an affair with a colleague's wife

Around 2000 Jeffrey Toobin entered into an extramarital affair with the daughter of former CNN senior analyst Jeff Greenfield, lawyer Casey Greenfield. According to The New York Times, the relationship lasted almost a decade, with Greenfield becoming pregnant in 2008. Toobin didn't handle that situation well. A source told the Daily News that Toobin kept telling Greenfield that he was leaving his wife, but she "had begun to distrust him" and "suspected he had several other mistresses."

When Greenfield approached Toobin with the pregnancy news, he reportedly offered her money to have an abortion. "When Casey wouldn't have an abortion, Jeff told her she was going to regret it, that she shouldn't expect any help from him," another source told the Daily News. Toobin then reportedly refused to provide a DNA sample, "stopped talking to [Greenfield]," and ignored an invitation to meet the child on the day of his birth. Toobin eventually agreed to the paternity test, and was ordered to pay child support, however he also allegedly refused to pay and only complied when threatened with wage garnishment.

The New York Times additionally reported that Greenfield "briefly represented herself" during the paternity litigation and she retained full custody of their son. "I had a job at a prestigious firm, a law degree from Yale that was paid for, a wonderful support group of friends," she said, explaining her decision not to get an abortion.

Salacious stories about Jeffrey Toobin have followed him for years

In 2010, the Daily News ran a blind item that alleges Toobin sexually harassed a "well-known media figure" after meeting her in 1995. "I was at a party in Washington," the woman said. "He came up behind me and whispered in my ear. I didn't even know who he was. I couldn't believe my ears. It was so disgusting. At the time, I never even knew people did that."

The woman went on to say that Toobin followed her to her hotel room and "tried to invite himself in," but the encounter ended there. She also claimed that Toobin continued to "[chase her] for a while," leaving her "several sick messages" on her phone using "vile" terminology. While the Daily News refused to print what Toobin allegedly told her, Gawker had no qualms, publishing graphic claims from an anonymous "tipster" who alleged that "multiple women" attested to Toobin's... unconventional sexual preferences. 

As of this writing, none of the women from either story have publicly come forward with accusations against Toobin. 

Patty Hearst has no time for Jeffrey Toobin

The kidnapping of Patty Hearst remains one of the most bizarre cases in American history. The granddaughter of newspaper magnate William Randolph Hearst, Patty was abducted from her Berkley, Calif. apartment in 1974 by urban guerrilla group the Symbionese Liberation Army (SLA) when she was just 19. Two months later, Hearst had seemingly joined the movement and helped them rob a bank.

She became a fugitive and was eventually caught and sentenced to prison, but her sentence was commuted by President Jimmy Carter after she served 21 months. Per History, Hearst claimed "she had been brainwashed." She sought to stay out of the public eye since the kidnapping, which she claims included "torture and rape," and has become involved with charities to help fight Alzheimer's disease and children afflicted with AIDS. She feels unfairly portrayed in the media depictions of her and routinely speaks out against movies and books about her life. "People don't let go. They just don't," she told The Los Angeles Times in 1988.

According to Page Six, Jeffrey Toobin received Hearst's sharpest criticism. The outlet reported that she told a friend that Toobin was "an emotional rapist" because of his 2017 book, American Heiress (Toobin also served as executive producer on CNN's docuseries The Radical Story of Patty Hearst). Per Deadline, Hearst released a statement saying she was "saddened and appalled" over the film adaptation of the book, and that "Toobin's distorted lens" further perpetuated "a one-sided dialogue romanticizing" her horrific ordeal. 

Hillary Clinton probably isn't a big Toobin fan, either

The revelation that Hillary Clinton used a private email server while she was Secretary of State became a massive story during the 2016 election. It was such an effective campaigning topic for Donald Trump that Clinton blamed the subsequent FBI investigation for sinking her bid for the presidency. In 2019, the State Department investigation into the matter found that Clinton didn't mishandle classified information. "While there were some instances of classified information being inappropriately introduced into an unclassified system in furtherance of expedience," the report said," there was no persuasive evidence of systemic, deliberate mishandling of classified information" (via The New York Times).

Once the findings of the investigation were released, Jeffrey Toobin issued a mea culpa of sorts. "Note the mostly buried news that State Dept closed @HillaryClinton email probe with this verdict: no big deal. As a journalist, I regret my role in blowing this story out of proportion," he tweeted. He went even further during an appearance on CNN, saying it was a "lesson learned" (via The Washington Post).

"This is also a story about the news media, about how much time we spent on that," Toobin said during the broadcast. "And that's something that I have felt a great deal of personal responsibility for because I talked about the emails here at CNN, I wrote about it in the New Yorker and I think I paid too much attention to them and I regret that."

The Zoom call that took Jeffrey Toobin down

On Oct. 19, 2020, Vice published a bombshell report stating that Jeffrey Toobin was suspended by The New Yorker after he allegedly exposed himself and performed a lewd act during "an election simulation" conducted via Zoom video chat between New Yorker and WNYC radio employees. According to two sources present on the chat, participants were on a break from "a strategy session," when Toobin appeared to be "on a second video call." He then reportedly lowered the camera and was seen touching himself. 

"I made an embarrassingly stupid mistake, believing I was off-camera. I apologize to my wife, family, friends and co-workers," Toobin told the publication. "I believed I was not visible on Zoom. I thought no one on the Zoom call could see me. I thought I had muted the Zoom video," he added. New Yorker spokesperson Natalie Raabe confirmed the suspension and an ongoing investigation.

Toobin will also be missing from CNN for the immediate future. "Jeff Toobin has asked for some time off while he deals with a personal issue, which we have granted," a spokesman for the network said. Masha Gessen, a New Yorker writer who was also present on the call, told The New York Times did offer Toobin this gracious concession: "I suspect he thought that when the breakout rooms started, he was disconnected and he didn't realize we'd all returned to a live camera." 

Is Jeffrey Toobin's career over?

After the Vice story broke, the debate began on whether or not the Zoom incident could be the final straw that ended Jeffrey Toobin's career. "Let's just be clear...there is no way the New Yorker and CNN are going to keep Jeffrey Toobin on the payroll," freelance journalist Yashar Ali tweeted. "He didn't get caught on a zoom changing his pants or something... They may go through the formality of investigations but he will not be kept on."

Atlantic staff writer Conor Friedersdorf tweeted that "we should react w/ empathy, politeness, & forgiveness, as we would want to be treated, rather than punitive mockery" to Toobin's lewd actions. Meghan McCain disagreed, replying that what Toobin did amounted to "assault and perversion." She also attributed his behavior to "the patriarchy," and advised his defenders to "stop trying [to] mansplain away this sicko."

However, Evan Nierman of the crisis management and P.R. firm Red Banyan, said that Toobin's actions might not be "a career killer." He added, "Was it a terrible decision? Yes, but I'm not sure it should end his career." Insiders at CNN agreed, telling Fox News that Toobin is "one of the biggest faces on the network" and "too valuable of a commodity" to fire so he would "probably" return to the network.