October
Jeffrey Toobin

Toobin was born to a Jewish American family in New York City in 1960, a son of Marlene Sanders, former ABC News and CBS News correspondent, and Jerome Toobin, a news broadcasting producer. His younger brother, Mark, born in 1967 with Down syndrome, lived apart from the family. He attended Columbia Grammar & Preparatory School, and then Harvard College for undergraduate studies. He covered sports for The Harvard Crimson, where his column was titled "Inner Toobin". Toobin graduated magna cum laude with a Bachelor of Arts degree in American history and literature, and was awarded a Harry S. Truman Scholarship. He then attended Harvard Law School, where he was classmates with Elena Kagan and graduated magna cum laude with a J.D. in 1986. While there, he was an editor of the Harvard Law Review

Toobin began freelancing for The New Republic while a law student. After passing the bar, he worked as a law clerk to a federal judge and then as an associate counsel for Independent Counsel Lawrence Walsh during the Iran–Contra affair and Oliver North's criminal trial. He next served as an Assistant United States Attorney for the Eastern District of New York in Brooklyn.

Toobin wrote a book, Opening Arguments: A Young Lawyer's First Case: United States v. Oliver North, about his work in the Office of Independent Counsel, to which Walsh objected. Toobin went to court to affirm his right to publish. Judge John F. Keenan of the United States District Court for the Southern District of New York wrote an opinion that Toobin and his publisher had the right to release this book. Before Walsh's appeal could be decided, the book was published, mooting the case. Accordingly the Circuit Court vacated the lower court's decision and ordered that the case be dismissed

Toobin was widely ridiculed in the wake of the incident by, among others, Jimmy Fallon, Donald Trump Jr., and Saturday Night Live. Defenders included former New Yorker editor Tina Brown, who said that "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." Author and journalist Malcolm Gladwell said he "read the Condé Nast news release, and I was puzzled because I couldn't find any intellectual justification for what they were doing."

On June 10, 2021, Toobin returned to CNN as its chief legal analyst. He described his conduct as "deeply moronic and indefensible" and said he "didn't think other people could see [him]", but admitted that this was no defense for his behavior. He said the time he spent off air went toward "trying to be a better person", working on his upcoming book about the Oklahoma City bombing, doing therapy, and working at a food bank.