Opinion: The Chickens Come Home to Roost for CNN's Jeffrey Toobin

It’s been fascinating over the last few days to watch the spectacular fall of Jeffrey Toobin, as well as the fallout from it.

Toobin, CNN’s chief legal analyst, was suspended from New Yorker magazine Tuesday after taking part in a Zoom conference call last week where he not only literally exposed himself but also got caught, um, taking matters into his own hands – if you catch my drift.


Without going into further detail on that front, some have pointed out that though gross, getting caught with his pants down isn’t the worst thing Toobin is known for. Back in the early 2000s, Toobin – who is married and has two children with his wife – had a long-running affair with a woman named Casey Greenfield. At one point, she became pregnant by Toobin. Though she had the child, it was reported later that Toobin was such a concerned lover that he actually offered to pay for Greenfield to have an abortion.

According to a source, when she refused, Toobin told her she shouldn’t expect any help from him. The New York Daily News wrote about the details of their on-again/off-again affair at the time:

“Jeff and Casey saw each other off and on over the years,” says one source. “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.”


Greenfield underwent a risky DNA test while pregnant, but Toobin didn’t provide his sample and stopped talking to her, according to sources. On the day she gave birth, Greenfield e-mailed Toobin, inviting him to meet his son, Rory. A source says Toobin didn’t reply.

Toobin ultimately cooperated with a DNA test that proved he was Rory’s dad. In February, a Manhattan Family Court judge ordered him to pay child support. When he refused to pay the full amount, say sources, Greenfield’s lawyer threatened to notify his employers and garnish his wages; Toobin then paid up.


Sounds like a real peach of a guy, doesn’t he?

But Toobin’s sordid history is even deeper than you might think.

In his newsletter last night, former CNN producer Steve Krakauer detailed other instances of Toobin’s (alleged) abhorrent treatment of women, details that until now have not been well-known to the public:

But that’s not it. Toobin was accused in 2010 of whispering “disgusting” things to a prominent woman, then following her to her hotel room and trying to invite himself in, before leaving her “vile” and “sick” messages in the days after. Want more details on the nature of the literally unprintable comments? Go to the old Gawker for that.

In 2015, Toobin was accused of “exploiting” a woman’s story for his own financial gain, writing a biography of her that caused her to allegedly describe him as “an emotional rapist.”

This, the same Jeffrey Toobin who, in recent years, has added moralizing anti-Trump pundit to his previous legal analysis for CNN. Like in 2018, during the Brett Kavanaugh hearings, when he described the allegations against Kavanaugh (never prosecuted or proven) this way: “If you sexually assault someone in high school, your life should be ruined.… how about the lives of the women? How about 15-year-old Ms. Blasey? How about her life?

So all of Toobin’s moralizing and preaching about treating women with respect was obviously empty, hollow rhetoric that he didn’t believe should be applied to himself. Which must be exactly why instead of suspending him, too, that CNN higher-ups have agreed to simply allow Toobin some time off to “reflect” on his actions, with the assumption being that he will return at a later point.


After all, the rest of the cast of characters at CNN are noted hypocrites as well, on everything from following CDC guidelines during the pandemic to cries for more civility in the public discourse. Why should Toobin be any different?

Still, the Zoom scandal will leave an indelible stain on his legacy, and going forward, he’ll be known as the “respected” legal analyst whose career was nearly upended because he couldn’t keep it in his pants.


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