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Jeffrey Toobin
Jeffrey Toobin
Jeffrey Toobin
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Jeffrey Ross Toobin[1] (/ˈtuːbɪn/; born May 21, 1960) is an American lawyer, author, blogger, and legal analyst for CNN.[2][3]

Key Information

During the Iran–Contra affair, Toobin served as an associate counsel on its investigation at the Department of Justice. He moved from government and the practice of law into full-time writing during the 1990s, when he published his first books. He wrote for The New Yorker from 1993 until 2020,[4] when Toobin was fired for masturbating on-camera during a Zoom video conference call with co-workers. He apologized for his conduct and stated that he believed his camera was off during the incident.[5][6][7][8][9] He continues to serve as a legal analyst for CNN.

Toobin has written several books, including accounts of the 1970s Patty Hearst kidnapping and her time with the SLA, the O. J. Simpson murder case, and the Clinton–Lewinsky scandal. The latter two were adapted for television as seasons of FX's American Crime Story, with the Simpson case premiering in 2016.

Early life and education

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Toobin was born to a Jewish-American family[10] in New York City in 1960,[11] a son of Marlene Sanders, former ABC News and CBS News correspondent, and Jerome Toobin, a news broadcasting producer.[12] His younger brother, Mark, born in 1967 with Down syndrome, has lived apart from the family.[5]

Toobin attended Columbia Grammar & Preparatory School. While attending Harvard College for undergraduate studies, he covered sports for The Harvard Crimson.[13] 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 attended Harvard Law School, where classmates included Elena Kagan, and he served as an editor of the Harvard Law Review. He graduated in 1986 with a J.D., magna cum laude.[14]

Career

[edit]
Toobin promoting his book The Nine: Inside the Secret World of the Supreme Court at the 2007 Texas Book Festival

Toobin began freelancing for The New Republic while a law student. After passing the bar exam, he worked as a law clerk to U.S. circuit judge J. Edward Lumbard of the U.S. Court of Appeals for the Second Circuit. Next he served as an associate counsel for Independent Counsel Lawrence Walsh during the Iran–Contra affair and Oliver North's criminal trial. He moved to serve as an Assistant United States Attorney for the Eastern District of New York in Brooklyn.[15]

Toobin wrote a book, Opening Arguments: A Young Lawyer's First Case: United States v. Oliver North (1991),[16] about his work in the Office of Independent Counsel, to which Walsh objected. Toobin had been required to sign multiple agreements to protect the confidentiality of grand jury and internal proceedings of the office. But he had taken thousands of pages of notes with him and based his book on such information, revealing material that Walsh believed should have been held as private. 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. The book was published before Walsh's appeal could be decided, mooting the case. Accordingly, the Circuit Court vacated the lower court's decision and ordered the dismissal of the case.[17]

After three years as an Assistant U.S. Attorney, Toobin resigned from the U.S. Attorney's office in Brooklyn, and abandoned "the practice of law."[citation needed] He started working as a writer at The New Yorker in 1993 and became a television legal analyst for ABC in 1996.

Toobin has provided broadcast legal analysis on several high-profile cases. In 1994, Toobin broke the story in The New Yorker that the legal defense team in O. J. Simpson's criminal trial planned to accuse Mark Fuhrman of the LAPD of planting evidence.[18] Toobin provided analysis of Michael Jackson's 2005 child molestation trial,[19] the O. J. Simpson civil case, and independent prosecutor Kenneth Starr's investigation of President Bill Clinton.

He published books on some of these cases: The Run of His Life: The People v OJ Simpson (1997), and A Vast Conspiracy (1999), about the investigation of Clinton for the Monica Lewinsky sex scandal. Each of these books was later adapted for television, the Simpson case as a mini-series, and the Clinton as an episode.

In 2000, Toobin received an Emmy Award for his coverage of the Elián González custody saga, which had resulted in the return of the boy from the United States to communist-led Cuba.

Toobin joined CNN in 2002[18] as a legal analyst. In 2003, he secured the first interview with Martha Stewart about the insider trading charges against her.[4]

Toobin speaking about the Supreme Court at the John J. Rhodes Lecture in Tempe, Arizona

Toobin is the author of seven books. His book The Nine: Inside the Secret World of the Supreme Court (2007) received awards from the Columbia University Graduate School of Journalism and the Nieman Foundation for Journalism at Harvard University.[18]

His next book was The Oath: The Obama White House and the Supreme Court (2012). American Heiress: The Kidnapping, Crimes and Trial of Patty Hearst (2016), explored events from the 1970s. All were New York Times Best Sellers.

He wrote True Crimes and Misdemeanors, the Investigation of Donald Trump (2020), described as a "summation for the jury" against the character and presidency of Donald Trump, as if he were on trial.[20]

On August 12, 2022, Toobin announced via Twitter that he would leave CNN after 20 years. His last day on air was August 4.[21] In February 2024, Toobin began appearing again on CNN as a frequent guest, offering analysis on both president Biden and former president Trump's current legal situations.[22]

Adaptations

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Two of Toobin's books were adapted for television. His book on the OJ Simpson trial was adapted as The People v. O.J. Simpson: American Crime Story, a 2016 mini-series comprising the first season of the FX true-crime anthology series.[23] A Vast Conspiracy (1999), about the Clinton-Lewinsky scandal, was adapted as a series, Impeachment: American Crime Story (2021), in the FX anthology.[24]

Zoom masturbation incident

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On October 19, 2020, during the first year of the COVID-19 pandemic, Toobin was suspended from The New Yorker after he masturbated on camera during a Zoom video call between New Yorker and WNYC radio staffers.[5][6][7][8][9] CNN said Toobin "has asked for some time off while he deals with a personal issue, which we have granted". Toobin said in a statement: "I made an embarrassingly stupid mistake, believing I was off-camera. I apologize to my wife, family, friends and co-workers."[25] In November 2020, he was fired from The New Yorker, following an internal investigation by the parent organization, Condé Nast.[26] New York Public Radio, which owns WNYC, indefinitely banned Toobin from its broadcasts and podcasts.[5]

Toobin was widely ridiculed in the wake of the incident by, among others, O. J. Simpson, Jimmy Fallon, Bill Maher, Donald Trump Jr., and performers on Saturday Night Live.[27] Irene Katz Connelly pointed out the parallels between him positioning perpetrators of sex scandals as victims in his writing with his response to the zoom incident.[28] Defenders included Tina Brown, a former New Yorker editor, 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." Canadian 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."[5]

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, going to therapy, and working at a food bank.[29]

Personal life

[edit]
Toobin in 2017

In 1986, Toobin married Amy Bennett McIntosh, whom he met in college while they worked at The Harvard Crimson. She is a 1980 Harvard graduate, holds an MBA degree from Harvard Business School,[1][13] and has held executive positions at Verizon Communications and Zagat Survey.[30] They have two adult children, a daughter and son.[30]

Toobin had a longtime off-and-on extramarital affair with attorney Casey Greenfield, the daughter of American television journalist and author Jeff Greenfield and his first wife, Carrie Carmichael. Casey Greenfield was formerly married to screenwriter Matt Manfredi.[31] Greenfield gave birth to Toobin's son in 2009; Toobin initially resisted acknowledging the boy. Toobin's paternity was confirmed with a DNA test as part of a suit by Greenfield for custody and child support.[32]

Publications

[edit]

Books

[edit]
  • Toobin, Jeffrey (1991). Opening arguments: a young lawyer's first case, United States v. Oliver North. New York: Viking.
  • — (1992) [1991]. Opening arguments: a young lawyer's first case : United States v. Oliver North. Revised & updated ed. New York: Penguin.
  • — (1997). The run of his life: the People v. O. J. Simpson.
  • — (1999). A vast conspiracy : the real story of the sex scandal that nearly brought down a president. New York: Random House.
  • — (2001). Too close to call : the thirty-six-day battle to decide the 2000 Election. New York: Random House.
  • — (2007). The Nine: Inside the Secret World of the Supreme Court. New York: Doubleday.[33]
  • — (2012). The Oath: The Obama White House and the Supreme Court. New York: Doubleday.
  • — (2016). American Heiress: The Wild Saga of the Kidnapping, Crimes and Trial of Patty Hearst. New York: Doubleday.
  • — (2020). True Crimes and Misdemeanors: The Investigation of Donald Trump. Knopf Doubleday Publishing Group. ISBN 978-0-385-53674-5.
  • — (2023). Homegrown: Timothy McVeigh and the Rise of Right-Wing Extremism. New York: Simon & Schuster.
  • — (2025). The Pardon: The Politics of Presidential Mercy. New York: Simon & Schuster.

Essays and reporting

[edit]

References

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[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Jeffrey Toobin

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from Grokipedia
Jeffrey Ross Toobin (born May 21, 1960) is an American lawyer, author, and former legal commentator who gained prominence as a for from 1993 to 2020 and as CNN's chief legal analyst from 2002 to 2022. Toobin authored several bestselling books on landmark legal cases and institutions, including The Run of His Life: The People v. (1996), which chronicled the Simpson murder trial, and The Nine: Inside the Secret World of the (2007), offering an insider's view of the U.S. . His career, marked by frequent on-air analysis of major trials and political legal developments, was significantly disrupted by a 2020 scandal in which he masturbated during a Zoom video conference with New Yorker colleagues and staff, believing the call had ended and he was participating in a separate video chat; this led to his immediate suspension and eventual termination from , as well as a temporary suspension from . Toobin returned to CNN on a part-time basis in June 2021 but departed the network entirely in August 2022 amid ongoing scrutiny of his professional conduct. Earlier in his career, Toobin worked as an appellate counsel at the U.S. Department of Justice and assisted in the Iran-Contra affair prosecution, establishing his legal expertise before transitioning to journalism.

Early Life and Education

Upbringing and Family Influences

Jeffrey Toobin was born on May 21, 1960, in to Jerome Toobin, a television news producer who served as news director at Channel 13 and worked as a producer for , and Marlene Sanders, a correspondent for ABC News and who became one of the first women to anchor a network news program after joining ABC in 1964. The family belonged to a Jewish background, with Sanders's side described as relatively secular. Toobin grew up on Manhattan's , spending his early years near 90th Street and Riverside Drive before his family moved to the West 70s. His parents' immersion in provided early exposure to the field; Jerome Toobin handled production logistics, while covered major stories as a trailblazing female reporter, including segments on civil rights and . This environment, marked by demanding schedules—such as Sanders working late shifts—saw Jerome Toobin stepping in for family duties like medical visits, fostering a household centered on media professionalism. Toobin attended Columbia Grammar School (later renamed Columbia Prep) in during his formative years. The dual journalistic careers of his parents later informed his own transition from to reporting, as he reflected on their influence in shaping his professional inclinations despite an initial pursuit of legal training. Jerome Toobin died in 1984, when Jeffrey was 24.

Academic Achievements and Early Interests

Toobin earned a bachelor's degree in American history and literature from in 1982. During his undergraduate years, he demonstrated an early interest in journalism by contributing to , where he wrote a sports column titled "Inner Toobin" and spent much of his time engaged in student reporting. He also served as editorial chairman of the publication, reflecting a blend of writing and analytical pursuits that foreshadowed his later career at the intersection of law and media. Following graduation, Toobin enrolled at , graduating with a J.D. magna cum laude in 1986. There, he edited the , a prestigious role indicating strong academic performance in legal scholarship and writing. His choice of law over was influenced by his parents—television producer Jerome Toobin and journalist —who, despite their media backgrounds, actively discouraged him from entering the field, prompting a pivot to legal studies while retaining an underlying interest in narrative and public affairs.

Professional Career

Following his graduation from in 1986, Toobin served as a to J. Edward Lumbard Jr., a judge on the United States Court of Appeals for the Second Circuit. In this role, he assisted in judicial decision-making at the federal appellate level, gaining early exposure to complex litigation. Toobin then joined the as an in the Eastern District of New York, based in , where he prosecuted federal criminal cases for approximately three years starting around 1987. His prosecutorial work focused on enforcing federal laws in areas such as fraud and public corruption, contributing to the office's caseload during a period of heightened scrutiny on and white-collar offenses in New York. Subsequently, Toobin transitioned to the Office of Independent Counsel Lawrence E. Walsh, investigating the Iran-Contra affair from roughly 1990 to 1992, extending his prosecutorial experience to a total of about six years in federal prosecution roles. There, he contributed to building cases against figures like , involving charges related to arms sales to and funding Nicaraguan in violation of congressional restrictions, though many convictions were later overturned on appeal. After this appointment concluded, Toobin left legal practice entirely to pursue and writing. No records indicate involvement in private litigation or civil practice during his legal career.

Entry into Journalism and Key Assignments

Toobin began his journalism career while still in law school at Harvard, freelancing articles for The New Republic. After completing clerkships, a stint as an assistant counsel in the Iran-Contra investigation, and private legal practice, he transitioned fully to reporting by joining The New Yorker as a staff writer in 1993, where he focused on legal affairs and high-profile trials. Among his earliest key assignments was comprehensive coverage of the murder trial in , beginning with the piece "An Incendiary Defense" in July 1994, which examined the defense team's strategy on , and continuing through "A Horrible Human Event" in October 1995, analyzing the acquittal's implications for race and in America. This reporting, spanning over a year, established Toobin as a leading chronicler of courtroom drama and informed his 1996 book The Run of His Life. Toobin later reported on the impeachment proceedings against President , producing "Terms of Impeachment" in September 1998, which detailed the House Judiciary Committee's deliberations on and obstruction charges, and "The Jester" in December 1998, profiling independent counsel Kenneth Starr's role amid partisan tensions. His on-site work during the 2000 election recount and the subsequent case Bush v. Gore yielded the 2001 book Too Close to Call, drawing from direct observation of ballot challenges and legal arguments that resolved the presidential contest on December 12, 2000. Additional assignments included the 1997 federal trial of Oklahoma City bomber and in-depth profiles of justices, such as those on and , which highlighted internal court dynamics and ideological shifts. These pieces underscored Toobin's approach to blending granular legal analysis with broader cultural and political context.

Television Commentary and Network Positions

Toobin began providing television legal commentary as an analyst for ABC News in 1996, following his mother into the network where he contributed to programs including . He covered high-profile legal matters, such as the trial aftermath and Clinton impeachment proceedings, establishing himself as a frequent on-air voice for network broadcasts. In 2002, Toobin joined CNN as a senior legal analyst, a role that expanded to chief legal analyst, where he appeared regularly on programs like Anderson Cooper 360° and election night coverage to dissect decisions, federal trials, and political scandals. His commentary often emphasized procedural intricacies and historical precedents, drawing on his prior experience as a federal prosecutor and appellate counsel. Over two decades, he analyzed events including the prosecutions, multiple presidential impeachments, and Trump-era investigations, positioning as a platform for his blend of legal expertise and narrative storytelling. Toobin's CNN tenure was interrupted on October 19, 2020, when the network suspended him indefinitely following reports of him exposing himself during a Zoom call with New Yorker and colleagues simulating election scenarios; stated the matter was under review. He returned to on-air duties on June 10, 2021, after an eight-month absence, resuming commentary on ongoing legal developments without public details on internal resolution. On August 12, 2022, Toobin announced his departure from after 20 years, citing a personal decision post-vacation, amid his prior firing from for the same incident.

Publications

Major Books and Their Themes

Toobin's debut major work, The Run of His Life: The People v. (1996), chronicles the 1994 murders of and , 's subsequent arrest, the infamous low-speed Bronco chase, and the ensuing criminal trial that captivated national attention from June 1994 through October 1995. The book emphasizes the trial's procedural missteps by the prosecution, including evidence handling errors like demonstration, alongside defense tactics that highlighted racial tensions in following the 1992 riots, ultimately leading to Simpson's acquittal on October 3, 1995. Toobin draws on extensive reporting to portray the contrasting worlds of Simpson's celebrity status and the victims' circle, underscoring how media frenzy and public polarization shaped perceptions of guilt and innocence. In A Vast Conspiracy: The Real Story of the That Nearly Brought Down a President (2000), Toobin examines the affair, which began in 1995 and escalated through Paula Jones's 1994 sexual harassment lawsuit against President , culminating in Clinton's December 1998 by the House on and obstruction charges related to his November 1998 testimony denying sexual relations. The narrative traces the interplay of personal indiscretions, independent counsel Kenneth Starr's investigation starting from the 1992 probe, and partisan motivations among Clinton's adversaries, framing the scandal as a collision of sexual privacy, , and political opportunism that ended with Clinton's February 1999 . Toobin critiques the expansion of civil litigation into political arenas, arguing it exemplified the legal system's overreach into governance. The Nine: Inside the Secret World of the (2007) offers an insider's analysis of the U.S. 's operations from the 1970s onward, focusing on the ideological shift from a liberal majority under Warren Burger to a conservative dominance solidified by 2005 under , with key cases like (1973) and (2000) illustrating justices' personal dynamics and decision-making. Based on interviews with justices and clerks, Toobin profiles figures such as and , highlighting internal tensions, strategic voting blocs, and the court's insulation from public scrutiny despite its profound influence on issues like , affirmative action, and . The book portrays the court less as an apolitical arbiter than as a body swayed by individual ideologies and alliances, exemplified by the 5-4 decisions in the 2000 election dispute. Toobin's American Heiress: The Wild Saga of the Kidnapping, Crimes and Trial of (2016) recounts the February 4, 1974, abduction of publishing heiress by the (SLA), her subsequent participation in a April 15, 1974, San Francisco bank robbery, and her 1976 federal trial for bank robbery, where she was convicted on March 20, 1976, and sentenced to seven years before a 1979 commutation by President . The account explores themes of coercion versus voluntary radicalization amid 1970s countercultural violence, the SLA's Marxist-Leninist ideology, and Hearst's defense of , which failed to sway the jury despite FBI manhunt details and her 1975 . Toobin contextualizes the episode within broader American anxieties over and class privilege, rejecting simplistic brainwashing narratives in favor of Hearst's agency in aligning with her captors.

Notable Essays, Reporting, and Contributions

Toobin's tenure as a at The New Yorker from 1993 to 2020 produced a body of legal reporting and essays that dissected high-profile trials, dynamics, and political scandals, often revealing insider strategies and personal motivations behind legal maneuvers. His coverage emphasized evidentiary details and procedural tactics, contributing to broader public comprehension of complex cases. A pivotal early piece was "An Incendiary Defense," published in the July 25, 1994, issue, which disclosed the defense team's plan—led by —to hire a to probe Mark Fuhrman's history of racial epithets, thereby preempting and amplifying claims of police bias in the double-murder trial. This reporting, drawn from direct access to defense sources, marked a turning point by elevating racial distrust narratives over forensic evidence like DNA matches, influencing trial strategy and media focus for months. Toobin followed with "A Horrible Human Event" in the October 23, 1995, issue, analyzing the through the lens of dynamics and prosecutorial missteps in the courtroom. Toobin's Supreme Court profiles offered granular examinations of justices' ideologies and influences, including "Heavyweight," a March 11, 2013, piece on that detailed her post-oral cancer treatment resilience, strategic dissents, and role in gender equality precedents like (1996). "No More Mr. Nice Guy," from May 18, 2009, scrutinized John Roberts's first-term decisions, arguing his consensus-building facade masked a conservative evident in cases like (2007) upholding partial-birth abortion restrictions. Similar in-depth reporting covered in "Swing Shift" (September 12, 2005), highlighting his pivotal swings on issues from to executive power, as well as profiles of and . Beyond the judiciary, notable essays included "The Dirty Trickster" (June 2, 2008), which chronicled Republican operative Roger Stone's Nixon-era tactics and involvement in scandals like the prostitution ring, and "The Man Who Terrifies Wall Street" (May 9, 2016), profiling U.S. Attorney Preet Bharara's indictments of insiders like SAC Capital's Steven Cohen for . These works underscored Toobin's method of embedding with subjects to uncover causal links between personal ambition and legal outcomes, though his interpretations sometimes aligned with prevailing institutional views on accountability in finance and politics.

Media Adaptations

Adaptations of Toobin's Works

Toobin's 1996 book The Run of His Life: The People v. O.J. Simpson served as the primary source for the FX anthology series The People v. O.J. Simpson: American Crime Story, which premiered on February 2, 2016, and dramatized the 1994–1995 murder trial of O.J. Simpson. The ten-episode limited series, developed by Scott Alexander and Larry Karaszewski, earned critical acclaim, including 22 Emmy nominations and wins for outstanding limited series, with Cuba Gooding Jr. receiving the award for lead actor in a limited series. Toobin, who covered the trial extensively as a legal correspondent, noted in interviews that the adaptation captured the book's focus on the trial's procedural intricacies and cultural impact while incorporating dramatic liberties for television pacing. His 1999 book A Vast Conspiracy: The Real Sex Scandal That Nearly Brought Down a President, examining the and subsequent impeachment proceedings, formed the basis for the third season of , subtitled , which debuted on on September 7, 2021. The seven-episode arc, produced by Ryan Murphy and featuring as , emphasized the book's analysis of the scandal's political machinations, media frenzy, and legal battles from 1995 to 1999. It received mixed reviews for its handling of character motivations but garnered Emmy nominations, including for limited series and lead actress. Toobin did not participate directly in the production, though the series drew on his reporting of events like Paula Jones's and Starr's investigation. No other completed adaptations of Toobin's works into or television have been produced as of , though a planned biopic based on his 2016 book American Heiress about was announced in 2017 with directing but abandoned by Twentieth Century Fox in January 2018 following objections from Hearst regarding factual inaccuracies. Similarly, his 2023 book Homegrown on has been optioned for television but remains undeveloped.

Involvement in Documentaries and Series

Toobin served as for the four-part CNN documentary The Radical Story of , which premiered on February 11, 2018, and examined the 1974 kidnapping of heiress by the , her subsequent involvement in bank robberies, and her trial. The series drew from firsthand accounts and archival footage to explore themes of privilege, , and media influence, with Toobin contributing on-location reporting from sites in the related to the events. Toobin appeared as a featured commentator in the ESPN documentary O.J.: Made in America, a five-part series directed by that debuted at the and aired in June 2016, chronicling O.J. Simpson's life, football career, the 1994 murders of and , and the ensuing trial. His insights, drawn from his coverage of the trial for and his 1996 book The Run of His Life, addressed the defense strategy, racial dynamics, and media's role in shaping public perception of the case. The series received the Academy Award for Best Documentary Feature in 2017. In 1995, provided an extended interview for the Frontline episode "The O.J. Verdict," broadcast on October 4, 2005, as part of the program's retrospective on the Simpson trial, where he discussed the defense team's tactics, including the use of race as a factor and the glove demonstration's impact. This appearance built on his contemporaneous reporting, highlighting his role as an on-the-ground observer during the trial's 1995 proceedings.

Controversies

2020 Zoom Call Incident and Immediate Aftermath

On October 15, 2020, Jeffrey Toobin participated in a private Zoom video conference call involving staff from magazine and radio, organized to conduct a simulated election-night scenario ahead of the U.S. . During the call, Toobin muted his audio but failed to disable his video feed, leading multiple participants to observe him exposing and stroking his erect penis while appearing to engage in a separate personal activity. Toobin abruptly left the meeting and later rejoined without video enabled, after which a colleague privately alerted him to the exposure. Toobin subsequently issued a public statement claiming the incident was unintentional, asserting that he believed his video was off and that he had joined what he thought was a separate call. He described it as an embarrassing mistake, apologizing to colleagues, friends, and family without elaborating further on the circumstances. Participants on the call, however, reported that Toobin seemed aware of the group setting initially and continued the behavior for several minutes despite visible cues from others, raising questions about the plausibility of his account, though no formal contradiction was immediately issued by . The New Yorker announced Toobin's suspension without pay on October 19, 2020, stating it was conducting an investigation into the matter and emphasizing that such behavior was incompatible with professional standards. CNN, where Toobin served as chief legal analyst, placed him on leave the same day, citing the need to review the incident internally. Initial media coverage focused on the breach of workplace etiquette amid the rise of remote work during the COVID-19 pandemic, with outlets like Vice and The New York Times highlighting the incident's disruption to the professional simulation without speculating on motives beyond Toobin's stated error.

2010s Affair, Paternity Dispute, and Family Revelations

In the late 2000s, Jeffrey Toobin, who was married to Amy McIntosh and father to two children with her, began an extramarital affair with Casey Greenfield, a graduate and daughter of colleague . The relationship, which reportedly lasted over a decade on an intermittent basis, became public knowledge through gossip columns in 2009 and 2010. Greenfield, who had been married to screenwriter prior to the affair, became pregnant in 2008 and informed Toobin, who offered her money to have an , according to sources close to the situation. Greenfield gave birth to a son, Roderick "Rory" Henry Greenfield, on March 19, 2009, naming him after her then-partner Jacob Labby (Roderick from his middle name) and her grandfather (Henry). Toobin initially resisted acknowledging paternity and declined to be listed on the birth certificate or provide voluntary support, prompting Greenfield to undergo a prenatal DNA test to establish fatherhood, which carried medical risks. The test confirmed Toobin as the biological father, leading to a contentious legal dispute over custody and child support filed in Manhattan Family Court in early 2010. Court proceedings revealed acrimony, including Toobin's contestation of Greenfield's claims regarding his involvement and her custody arrangements with Labby, who had been raising as his own. In February 2012, a Family Court judge ordered Toobin to pay $6,000 monthly in plus $250,000 in legal fees to Greenfield, affirming his financial obligations while custody remained primarily with her and Labby. Toobin later described the episode as a personal failing but maintained limited involvement with , who grew up knowing his biological father through court-mandated interactions. The scandal exposed fractures in Toobin's family life, highlighting his amid his public persona as a legal commentator; it strained but did not end his to McIntosh, with whom he continued to raise their and . Revelations from the dispute, amplified by media coverage in outlets like the and New York Times, underscored Toobin's prioritization of professional discretion over personal accountability, as he initially sought to keep the matter private despite its escalation into public litigation. No formal from McIntosh occurred as a direct result, though the affair contributed to ongoing scrutiny of his private conduct in subsequent years.

Personal Life

Marriages, Relationships, and Children

Toobin married Amy Bennett McIntosh, a former executive at Verizon and Survey, in 1986; the couple remained married as of 2021, marking 35 years together despite public scandals. They have two adult children from the , though their names and specific details remain private. During his marriage, Toobin engaged in a decade-long extramarital affair with attorney Casey Greenfield, daughter of former CNN executive Jeff Greenfield and 13 years his junior; the relationship was on-and-off, beginning around the early 2000s. Greenfield became pregnant in 2008, and Toobin reportedly offered her money to terminate the pregnancy while initially questioning paternity. She gave birth to a son, Rory, in March 2009; a prenatal DNA test confirmed Toobin's paternity, leading to a cooperative time-sharing arrangement without major custody disputes, though Toobin contested some financial aspects. Toobin reportedly promised to leave McIntosh for Greenfield at points during the affair but did not follow through, contributing to its eventual end; by 2011, he sought to reconcile with his wife amid the ongoing paternity fallout. The family maintained a low profile in their $2.7 million home following later controversies, with Toobin and McIntosh appearing together publicly in November 2020. No other long-term relationships or children have been publicly documented.

Health Issues and Private Challenges

Toobin's family has encountered significant health-related challenges. His younger brother, Mark, born in 1967, has and has lived separately from the immediate family, most recently in a in . An older brother died of prior to Mark's birth, contributing to early familial hardships. These circumstances shaped Toobin's upbringing, with Mark requiring specialized care that distanced him from the household. No public records indicate major personal health conditions affecting Toobin himself.

Later Career and Reception

Post-2020 Professional Trajectory

Following his suspension from on October 19, 2020, amid the Zoom call incident, Toobin was terminated from the magazine on November 11, 2020, ending a 27-year tenure as a staff writer. He had also requested a from , where he served as chief legal analyst since 2002. Toobin returned to CNN on June 10, 2021, resuming his role as chief legal analyst after an eight-month hiatus. He contributed commentary on legal matters, including decisions and political trials, through at least mid-2022. In August 2022, Toobin departed , transitioning away from the full-time analyst position nearly two years after the incident. Post-departure from CNN, Toobin focused on authorship and selective media appearances. His book The Pardon: The Politics of Presidential Mercy was published by Simon & Schuster in February 2025, examining the historical and political dimensions of executive clemency. He promoted the work through keynote speeches, such as at the White Collar Conference on October 11, 2025, and radio slots, including a segment on KBLA on October 12, 2025. Occasional commentary persisted, with Toobin critiquing legal developments like Donald Trump's financial claims against the government in October 2025. No formal return to The New Yorker occurred, and his professional output shifted toward independent writing and guest analyses rather than staff affiliations.

Public Perception, Achievements, and Criticisms

Toobin's achievements in legal journalism include authoring several best-selling books that dissect landmark American trials and political events, such as The Run of His Life: The People v. O.J. Simpson (1996), which offered a comprehensive narrative of the 1994–1995 murder trial based on extensive reporting, and American Heiress: The Wild Saga of the Kidnapping, Crimes and Trial of Patty Hearst (2016), lauded for its meticulous reconstruction of the 1974 kidnapping and subsequent legal proceedings. Other notable works encompass A Vast Conspiracy (1999), detailing the Clinton-Lewinsky scandal, and Too Close to Call (2001), analyzing the 2000 presidential election recount. These publications, grounded in primary interviews and court records, established him as an authoritative chronicler of legal history, with adaptations like the FX series The People v. O.J. Simpson drawing from his Simpson book. Professionally, Toobin earned an Emmy Award in 2001 for his television coverage of the custody dispute, highlighting his role as a broadcast legal analyst. He received the 2015 Randy Shilts Award from the National Lesbian and Gay Journalists Association for distinguished LGBTQ+ coverage, reflecting recognition within niche journalistic circles. His tenure as a at The New Yorker from 1993 to 2020 and chief legal analyst at underscored his influence, with commentary appearing across major outlets on decisions and . Public perception of Toobin portrays him as a seasoned legal commentator whose analytical depth garnered respect pre-2020, yet whose personal scandals have persistently overshadowed his expertise, fostering skepticism about his judgment in professional settings. By 2025, following his departure from in August 2022 after two decades—amid lingering fallout from earlier incidents—he shifted to contributing opinion columns at , where he critiques topics like presidential pardons and judicial ethics, signaling a rehabilitation in elite media circles. His upcoming , : The Politics of Presidential Mercy (February 2025), continues this trajectory, though public discourse often references his past as a punchline, as seen in conservative critiques dubbing him a "renowned masturbator" in reference to the 2020 Zoom incident. Criticisms of Toobin center on the perceived disconnect between his advocacy for accountability in legal scandals and his own conduct, with detractors arguing his 2021 return to after an eight-month suspension belittled #MeToo principles by prioritizing star power over workplace norms. Figures like have publicly mocked his post-scandal analyses, questioning his credibility on high-stakes trials given prior lapses in professional decorum. Some observers, including feminist commentators, have highlighted patterns of in his past evaluations of female politicians, such as dismissive remarks on their viability, though these remain anecdotal amid his broader liberal-leaning commentary, which aligns with mainstream media outlets but draws little substantiated critique for ideological bias in peer-reviewed or primary legal analyses. Despite these, no formal professional sanctions beyond temporary leaves have been documented, allowing his career persistence in opinion-driven roles.

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