Jeffrey Toobin's apparent career-killing decision to masturbate during a work Zoom meeting is far from the first time his obsession with sex has got him into trouble.
The married CNN pundit was also the subject of a high-profile paternity suit — and the mother of his child dumped him because of his numerous affairs.
Toobin, 60, has been suspended by The New Yorker after masturbating during a video conference held last week to discuss the magazine's election coverage. He says he thought his camera was off.
He has not appeared on CNN, where he is a legal analyst, since the weekend and the frequent tweeter's Twitter account has gone silent.
Toobin has been married to his Harvard classmate Amy McIntosh for 34 years. They have two daughters. But that didn't stop him having a decade-long on-off affair with 13-years-younger fellow lawyer Casey Greenfield.
Greenfield got pregnant in 2008 and her lover immediately questioned whether he was the parent, balking at taking a paternity test.
When she refused his money for an abortion, he made a counteroffer to 'swap' pregnancies — if she agreed to terminate her pregnancy he would pay for her to have a child with a sperm donor.
Jeffrey Toobin's apparent career-killing decision to masturbate during a work Zoom meeting is far from the first time that his obsession with sex has got him into trouble. He was spotted outside his Upper West Side apartment in New York with his dog first thing on Tuesday morning just one day after it was revealed the New Yorker magazine had suspended him
Toobin has been married to his Harvard classmate Amy McIntosh (pictured together) for 34 years. They have two daughters. But that didn't stop him having a decade-long on-off affair with 13-years-younger fellow lawyer Casey Greenfield
Greenfield got pregnant in 2008 and her lover immediately questioned whether he was the parent, balking at taking a paternity test. When she refused his money for an abortion, he made a counteroffer to 'swap' pregnancies — if she agreed to terminate her pregnancy he would pay for her to have a child with a sperm donor. Pictured: Greenfield and her son
Toobin made an appearance on CNN on Saturday where he is a chief legal analyst for the network. CNN has since said that Toobin had asked for some personal time off, which they have granted
But Greenfield, who was 35 at the time, decided to go ahead and have the baby boy, whom she called Rory. On the day she gave birth she emailed Toobin, inviting him to meet his son. He didn't reply.
Greenfield then sued her lover for child support, according to The New York Times. The case dragged through the courts for two years with Toobin contesting many aspects of his ex's case.
Eventually he took a DNA test that proved he was the father and Greenfield, the daughter of Toobin's former CNN colleague Jeff Greenfield, won full custody of the boy, and given all decision-making rights on his upbringing.
'Jeff and Casey saw each other off and on over the years,' one source told the New York Daily News at the time.
'She was married to someone else for two years. After her divorce, she started seeing Jeff again. He said he was going to leave his wife for her. But, by then, Casey had begun to distrust him. She suspected he had several other mistresses.'
Another source told the Daily News: 'When Casey wouldn't have an abortion, Jeff told her she was going to regret it, and that she shouldn't expect any help from him.'
Toobin was also described as a sexual predator. A woman the Daily News described as 'a well-known media figure' claimed he had approached her at a party many years earlier. 'He came up behind me and whispered in my ear,' she told the paper.
The pubication refused to say exactly what he allegedly said, claiming it was unfit for a family newspaper. 'I couldn't believe my ears. It was so disgusting. At the time, I never even knew people did that,' the media figure said.
Though the newspaper did not reveal what he was after, the now-defunct website Gawker had no such qualms. 'He had a bit of what could be deemed an anal fixation,' it reported.
When the woman turned him down, she described how he allegedly followed her to her hotel room. 'He tried to invite himself in. He said, 'You know you want it.' I said, 'No, actually I don't.'
Toobin was also described as a sexual predator. A woman the Daily News described as 'a well-known media figure' claimed he had approached her at a party many years earlier. 'He came up behind me and whispered in my ear,' she told the paper. The Daily News refused to say exactly what he allegedly said, claiming it was unfit for a family newspaper. 'I couldn't believe my ears. It was so disgusting. At the time, I never even knew people did that,' the media figure said
When the woman turned him down, she described how he allegedly followed her to her hotel room. 'He tried to invite himself in. He said, 'You know you want it.' I said, 'No, actually I don't'
Greenfield decided to go ahead and have the baby boy, whom she called Rory. On the day she gave birth she emailed Toobin, inviting him to meet his son. He didn't reply. Greenfield then sued her lover for child support, according to The New York Times. The case dragged through the courts for two years with Toobin contesting many aspects of his ex's case
'He really chased me for a while. He called me at the office and left several sick messages,' she said.
Toobin — who was once described as 'the Tiger Woods of legal journalism' — admitted visiting Velvet, a swingers' club in Miami with political fixer Roger Stone in a 2008 New Yorker article.
'A flat-screen television on the wall plays porn videos, and many clubgoers disappear into locker rooms and emerge wearing towels,' he wrote. 'From there, some of them go into a lounge, a Jacuzzi room, or one of about half a dozen private rooms to have sex—with their dates or with new acquaintances.'
Toobin did not reveal whether he actually hooked up in Velvet. He said Stone took him there because it is the place where a prostitute had told him of a date with former New York Governor Eliot Spitzer, which Stone later revealed, forcing Spitzer from office.
But it is his latest embarrassing brush with infamy that threatens to end Toobin's lengthy career. The New Yorker, where he worked for 25 years, has suspended him while it carries out an investigation.
The Zoom call was for an 'election simulation' — so the magazine could work out many different outcomes of the upcoming vote. Toobin was playing the role of the courts while colleagues including Jane Mayer, Evan Osnos, Jelani Cobb and Sue Halpern played political parties and attorneys.
Toobin — who was once described as 'the Tiger Woods of legal journalism' — admitted visiting Velvet, a swingers' club in Miami with political fixer Roger Stone (pictured with his wife in 2019) in a 2008 New Yorker article
Toobin did not reveal whether he actually hooked up in Velvet (pictured). He said Stone took him there because it is the place where a prostitute had told him of a date with former New York Governor Eliot Spitzer, which Stone later revealed, forcing Spitzer from office
The meeting broke off briefly but Toobin's camera kept rolling, two unidentified staffers say. He seemed to be on a second Zoom call when the break was over and people started returning to the video meeting room.
They say Toobin lowered his camera and he was seen touching his penis.
In a brief statement, Toobin said on Monday: 'I made an embarrassingly stupid mistake, believing I was off-camera.
'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. I apologize to my wife, family, friends and co-workers.'
A spokesperson for the New Yorker confirmed that Toobin had been suspended pending an investigation into the incident.
He last appeared on CNN, where he is the network's chief legal analyst, on Saturday.
CNN has since said that Toobin had asked for some personal time off and has taken a leave of absence.
'Jeff Toobin has asked for some time off while he deals with a personal issue, which we have granted,' a spokesperson for the network said.
Toobin, who regularly uses Twitter, has been silent on social media since October 13.
His potential downfall appeared to be the subject of hilarity among some of his television colleagues.
On Monday MSNBC hosts Chris Hayes and Rachel Maddow broke into fits of laughter when discussing 'the events of the day.' Neither specifically mentioned Toobin but it was clear what they were talking about as Hayes handed the network over to Maddow.
Later on Monday, MSNBC hosts Rachel Maddow and Chris Hayes (pictured) appeared to laugh about Toobin's ordeal on air. Many have suggested the pair were laughing over an agreement made earlier in the day to not address the Toobin controversy
Simpson wasted little time grabbing the opportunity to make fun of Toobin's latest predicament. ''Daaaaamn, Jeffrey Toobin. At least Pee-wee Herman was in an X-rated movie theater,' Simpson said, referring to the TV personality caught in the act in 1991 in a video post
Toobin's CNN colleague Jake Tapper snapped back angrily at the former NFL superstar on Twitter. 'You murdered your wife and an innocent man in cold blood. No one really needs to hear from you ever,' he said
'Good evening, Chris. Thank you so much, and thank you for your counsel over the course of today as a work day…' Maddow said before Hayes started laughing.
'It was such a weird day today.'
Hayes responded: 'I'm always happy to have those high-level editorial discussions with you about the most important stories in our world.'
Maddow added: 'Let us never speak of this publicly again. Thank you very much, my friend.
'It pays to have colleagues who share a sense of both the absurdity of life and the responsibility of what actually should be on television. And it really pays to be able to talk to those colleagues during the course of the day like today.'
Toobin has been a staff writer at the New Yorker since 1993 and a CNN contributor since 2002. Prior to joining CNN, he had worked at ABC as a legal expert from 1996.
He famously covered OJ Simpson's murder trial for the New Yorker in the 1990s and later wrote a book about his coverage that became the basis of FX's 2016 miniseries The People v. OJ Simpson: American Crime Story.
Simpson wasted little time grabbing the opportunity to make fun of Toobin's latest predicament. ''Daaaaamn, Jeffrey Toobin. At least Pee-wee Herman was in an X-rated movie theater,' Simpson said, referring to the TV personality caught in the act in 1991 in a video post. 'I'm just saying.'
Toobin's CNN colleague Jake Tapper snapped back angrily at the former NFL superstar on Twitter. 'You murdered your wife and an innocent man in cold blood. No one really needs to hear from you ever,' he said.
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