Toobin served as a legal analyst for CNN from 2002 to 2022, and was a staff writer for The New Yorker from 1993 to 2020.

Toobin was seen masturbating live on a Zoom call in late 2020, after mistakenly leaving his camera turned on. This event led to a suspension from his position at the New Yorker. He also took a leave of absence from CNN until mid 2021.