Jeffrey Toobin made headlines last year when he exposed himself on a professional Zoom call, reportedly masturbating on camera. The incident had the New Yorker writer and CNN analyst ousted from work, but he returned to CNN as the network’s chief legal analyst on Thursday.

For some, the eight-month hiatus wasn’t long enough, especially since this isn’t Toobin’s first controversial sex scandal. A decade before the zoom masturbation mess in October, the legal expert had a child out of wedlock with a notable attorney and was sued for child support.

The prolific author is a 60-year-old husband and father with a few too many demons in the closet. He had a baby with Casey Greenfield, the daughter of Jeff Greenfield, one of Toobin’s CNN colleagues. The 14-year age gap wasn’t enough to quell the sparks, and while working as a fact-checker for Glamour magazine, Greenfield became Toobin’s lover.

Casey Greenfield is a big name now, but before that she was working her way up through the ranks. In 2008, she was not only looking for a career, but an answer to her new dilemma: being single and pregnant in the corporate world. The baby’s father was a high-profile writer and best-selling author. His name: Jeffrey Toobin. The problem? Toobin was married.

Jeffrey Toobin's Sex Life Was Controversial In 2012! Zoom Masturbation Mess Wasn't The First Time The Legal Expert Got Into Problems.
Jeffrey Toobin’s Sex Life Was Controversial In 2012! Zoom Masturbation Mess Wasn’t The First Time The Legal Expert Got Into Problems. Photo Credit: Rob Crandall / Shutterstock.com

Their relationship spanned nearly a decade, according to a New York Times article, and Greenfield was sure that the child was his. Toobin, however, was skeptical, and he wasn’t going to admit fault without proof. In fact, Toobin was more than reluctant to accept his fault and instead balked at the idea of a paternity test, vowing to take no responsibility for the child. His arrogance was quickly punished.

A paternity test proved his relation, and Greenfield was not backing down without a fight. In 2012, Greenfield recalled her pregnancy and the predicament she found herself in. “The one time you really don’t want to get pregnant is when you’re single and the other person is married and you’re working as a first-year junior associate at a law firm in a hard-core phase of trying to prove yourself to them,” she explained, “I had a job at a prestigious firm,” she said, “a law degree from Yale that was paid for, a wonderful support group of friends.”

She decided to keep the child and when the boy was finally born, decided to name him Roderick Henry Greenfield. She also decided to sue for child support, after taking maternity leave to care for the baby boy.

The lawsuit ended, but not without a fight from Jeffrey Toobin. He lost custody of Rodrick, and Greenfield won the right to make pivotal decisions in the child’s upbringing. The tabloids ate up the story but Toobin resumed his high-profile career unscathed. His wife and family stood by him, despite an obvious sex scandal for the ages.

Now it seems Jeffrey Toobin has made it through another scandal after CNN allowed him to return as the network’s chief legal analyst. Eight months ago the legal expert was caught red-handed, or rather, right-handed, during a Zoom meeting with some of The New Yorker’s biggest names, as well as producers and workers from WNYC public radio.

In speaking on the incident, Toobin said: “I made an embarrassingly stupid mistake, believing I was off-camera.” He continued his admission of guilt, saying that “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.”

Jeffrey Toobin also said he “apologized to my wife, family, friends, and co-workers.’’ The scandal cost Toobin his job at The New Yorker. The magazine suspended the writer, though Toobin claims he took a leave of absence.

In speaking on his future, Toobin said that he is “sorry to the people who read my work and who watched me on CNN who thought I was a better person than this. And so, you know, I got a lot to rebuild, but I feel very privileged and very lucky that I’m going to be able to try to do that.”