Jeffrey Toobin began his career in law, serving as a law clerk for a federal judge and later as an associate counsel for the Iran-Contra investigation led by Lawrence Walsh. 1 He then worked as an Assistant U.S. Attorney in Brooklyn for three years before resigning in 1993. 2

Toobin transitioned into journalism and legal analysis, joining The New Yorker as a staff writer covering legal affairs in 1993. 12 He gained significant prominence for his coverage of the O.J. Simpson murder trial, breaking the news that Simpson's defense planned to accuse Mark Fuhrman of evidence planting. 3 Toobin's book "The Run of His Life" chronicled the trial. 3

In 1996, Toobin became a legal analyst for ABC News, and in 2002 he joined CNN as their chief legal analyst, a position he held until 2022. 32 He has provided analysis for numerous high-profile cases, including the Clinton impeachment, the Michael Jackson trial, and the Trump investigations. 34 Toobin has authored several bestselling books delving into major legal events and the U.S. Supreme Court. 134

Jeffrey Toobin has received numerous accolades for his exceptional journalism and legal analysis. In 2000, he was awarded an Emmy for his coverage of the Elián González custody saga. 12 His book "The Nine: Inside the Secret World of the Supreme Court" (2007) earned prestigious honors, including the J. Anthony Lukas Prize for Nonfiction from Columbia University and the Nieman Foundation at Harvard University. 13

Toobin has provided insightful analysis on many high-profile legal cases that captured national attention. He gained widespread recognition for his comprehensive reporting on the O.J. Simpson murder trial, which he chronicled in his bestselling book "The Run of His Life: The People v. O.J. Simpson." 14 He also offered legal expertise during the Michael Jackson child molestation trial and the Clinton-Lewinsky scandal, which he explored in his book "A Vast Conspiracy." 142

Jeffrey Toobin's personal life has been marked by controversies. In 1986, he married Amy Bennett McIntosh, with whom he has two children. 1 However, Toobin had a long-term extramarital affair with attorney Casey Greenfield, daughter of journalist Jeff Greenfield. 12 Greenfield gave birth to Toobin's son in 2009, but he initially denied paternity until a DNA test confirmed it, leading to a custody and child support suit. 12

Toobin faced significant backlash in October 2020 when he was caught masturbating during a Zoom call with colleagues at The New Yorker. 34 The incident, dubbed the "Toobin Missile Crisis," led to his suspension from The New Yorker and a leave of absence from CNN. 34 While The New Yorker ultimately fired him, CNN allowed Toobin to return in June 2021 after a seven-month hiatus, drawing criticism for the decision. 45

Additionally, reports surfaced that Toobin had once offered Greenfield money to have an abortion when she was pregnant with his child, further tarnishing his reputation. 3 Despite these controversies, Toobin has continued his career as a legal analyst, though his actions have raised questions about accountability and workplace conduct. 5

In August 2022, Jeffrey Toobin announced his departure from CNN after two decades as the network's chief legal analyst. 12 However, he has continued making guest appearances on CNN in 2023 to provide commentary on legal matters, such as former President Trump's indictments and the Supreme Court's rulings. 34

Toobin's return to CNN following his 2020 Zoom scandal has drawn mixed reactions. While some have praised his legal expertise, others have criticized the network's decision to bring him back, questioning accountability for his actions. 45 His past controversies, including an extramarital affair and allegations of pressuring his mistress to have an abortion, have further tarnished his public image. 25