Law, disrupted Re-release: A Conversation with Celebrated Legal Author Jeffrey Toobin
Oct 30, 2025
Join celebrated legal analyst Jeffrey Toobin, a bestselling author known for his deep dives into major legal stories, as he discusses his fascinating journey from law to journalism. He reveals insights from his clerkship on the Second Circuit and his experience as an Assistant U.S. Attorney. Toobin shares his disciplined writing routine, including his daily quota of 1,250 words. He delves into why trials captivate readers, the artistry of trial lawyers as storytellers, and reflects on unforgettable figures like Johnny Cochran and Sandra Day O’Connor.
52:33
From Clerkship To Iran-Contra
- Toobin left his clerkship early to work on the Iran-Contra investigation.
- That experience became his first book, Opening Arguments.
OJ Coverage Changed His Career
- Tina Brown hired Toobin at The New Yorker and sent him to cover the O.J. Simpson case.
- His O.J. coverage led to a bestselling book and TV contracts.
Daily Writing Quota
- Commit to a daily word quota to finish long projects reliably.
- Write 1,250 words a day, five days a week to produce a book in months.
Get the Snipd Podcast app to discover more snips from this episode
Get the app 1 chevron_right 2 chevron_right 3 chevron_right 4 chevron_right 5 chevron_right 6 chevron_right 7 chevron_right 8 chevron_right 9 chevron_right 10 chevron_right 11 chevron_right 12 chevron_right 13 chevron_right 14 chevron_right 15 chevron_right 16 chevron_right 17 chevron_right 18 chevron_right 19 chevron_right
Intro
00:00 • 43sec
Toobin's Career Path from Law to Journalism
00:43 • 5min
Early Legal Jobs and Summer Associate Experiences
05:46 • 1min
Learning to Write Through Student Journalism
07:02 • 2min
Book Project: Writing About Nixon's Pardon
09:06 • 24sec
Toobin's Daily Writing Routine and Quota
09:30 • 4min
Challenges of Getting Interview Subjects to Talk
13:11 • 2min
Unavailable Sources: Patty Hearst and O.J. Simpson
14:45 • 2min
Choosing Book Subjects: News vs. Original Stories
16:23 • 2min
Advantages and Challenges of Writing Historical Subjects
17:58 • 3min
When a Potential Book Fails: The Missing Transcript Problem
21:26 • 2min
Why Trial Books Captivate Readers
23:47 • 2min
The Trial Lawyer as Storyteller
25:34 • 2min
Favorite Books About Trial Lawyers
27:36 • 6min
Supreme Court Histories and WWII-era Decisions
34:01 • 8min
Unforgettable Lawyers: Cochran, Scheck, O'Connor
42:07 • 4min
F. Lee Bailey's Personality and Career
45:37 • 3min
Robert Caro and Concerns About His Final Volume
48:26 • 3min
Outro
51:30 • 44sec
#
The trial of Jack Ruby
John Kaplan
The Trial of Jack Ruby examines the legal proceedings following the shooting of Lee Harvey Oswald by Jack Ruby.
It explores the defense strategies, the prosecution's case, and the key events that shaped the outcome of the trial.
The book delves into the complex issues surrounding the assassination of JFK and the subsequent trial of his assassin's killer.
Through detailed analysis and historical context, the book sheds light on the legal and social climate of the time.
The Trial of Jack Ruby explores themes of justice, revenge, and the pursuit of truth in the wake of tragedy.
#
The People vs. Clarence Darrow
string
Geoffrey Cowan
The People vs.
Clarence Darrow explores the legal battles faced by famed attorney Clarence Darrow, including his trial for allegedly bribing a juror.
It details the evidence presented, the arguments made by both sides, and the ultimate outcome of the case.
The book provides a nuanced portrayal of Darrow, examining his complex personality, legal strategies, and impact on American jurisprudence.
Through historical context and legal analysis, the book sheds light on the challenges faced by lawyers who push the boundaries of the law.
It explores themes of justice, ethics, and the pursuit of truth in the legal profession.
#
How and Why I Work
string
Robert A. Caro
How and Why I Work offers insights into the writing process and research methods of Robert Caro, one of America's foremost biographers.
It explores his meticulous attention to detail, his dedication to understanding the lives of his subjects, and his unwavering commitment to truth.
The book also reveals his approach to historical research, including his emphasis on primary sources and his willingness to spend years immersed in the lives of his subjects.
Through personal anecdotes and practical advice, the book provides a guide for aspiring writers and biographers.
How and Why I Work celebrates the art of biography and the importance of telling stories that matter.
#
Opening arguments
Jeffrey Toobin
Opening Arguments offers a firsthand account of the Iran-Contra affair from the perspective of a young lawyer involved in the investigation.
It details the political intrigue, legal challenges, and personal experiences of the author as he navigates the complex world of government investigations.
The book provides insights into the key players, events, and controversies surrounding the scandal, examining the impact on American foreign policy and the rule of law.
Through vivid storytelling and legal analysis, the book captures the intensity and significance of the Iran-Contra affair.
Opening Arguments explores themes of justice, power, and the pursuit of truth in the face of political pressure.
#18236
• Mentioned in 2 episodes
A civil action
Jonathan Harr
A Civil Action by Jonathan Harr is a gripping non-fiction book that explores the true story of a legal battle against corporate giants accused of polluting a town's water supply.
The book follows Jan Schlichtmann, a lawyer who represents families affected by the contamination, as they navigate the complexities of environmental law and the pursuit of justice.
Despite securing a partial victory, the case takes a heavy toll on all involved.
#4075
• Mentioned in 9 episodes
Tinker, Tailor, Soldier, Spy
John Le Carré
In this novel, George Smiley is summoned from retirement to investigate a mole within the British intelligence service, known as the Circus.
The story unfolds as a cat-and-mouse game, with Smiley delving into the pasts of his suspects, each codenamed from a children’s nursery rhyme: Tinker, Tailor, Soldier, and Sailor.
The investigation is complex, involving office politics, personal betrayals, and the moral ambiguities of the espionage world.
Le Carré masterfully crafts a realistic and gripping narrative that critiques the espionage industry and its impact on individuals and society.
#
The Court at War
FDR, His Justices, and the World They Made
Cliff Sloan
The Court at War explores the pivotal period when President Franklin D. Roosevelt appointed seven of the nine Supreme Court justices, influencing the court's decisions during World War II. The book delves into the complex relationships between justices and their differing judicial philosophies, highlighting both progressive and controversial rulings like Skinner v.
Oklahoma and Korematsu v. United States.
#23415
• Mentioned in 2 episodes
Scorpions
Noah Feldman
Scorpions delves into the lives of Hugo Black, Felix Frankfurter, William O. Douglas, and Robert H. Jackson, four justices who shaped the modern Constitution during the tumultuous periods of the Great Depression, World War II, and the Cold War. The book highlights their complex relationships with each other and FDR, as well as their distinct judicial philosophies that continue to influence constitutional thought today.
#
Courting justice
from NY Yankees v. Major League Baseball to Bush v. Gore, 1997-2000
David Boies
#17620
• Mentioned in 2 episodes
Homegrown
null
Ben Hewitt
#34779
Gunning for Justice
Gerry Spence
In 'Gunning for Justice,' Gerry Spence recounts his experiences as a trial lawyer, providing insights into his personal life and legal philosophy.
The book reflects Spence's advocacy for the underdog and his passionate belief in the power of the jury system.
Spence shares anecdotes from his most famous cases, offering a behind-the-scenes look at the strategies and emotions involved in high-stakes litigation.
He emphasizes the importance of authenticity, storytelling, and connecting with jurors on a human level.
The book serves both as a memoir and a guide for aspiring trial lawyers, imparting Spence's unique approach to law and life.
#69758
The run of his life
The People v. O.J. Simpson
Jeffrey Toobin
This book provides a comprehensive and behind-the-scenes look at the O.J.
Simpson trial, often referred to as 'the trial of the century.
' Toobin chronicles the events from the murders to the trial, highlighting the strategic decisions and mistakes made by both the prosecution and the defense.
The narrative includes the roles of key figures such as Marcia Clark, Chris Darden, and Johnnie Cochran, and it analyzes the impact of media coverage and racial tensions on the trial's outcome.
#
American heiress
The Wild Saga of the Kidnapping, Crimes and Trial of Patty Hearst
Jeffrey Toobin
Jeffrey Toobin's 'American Heiress' delves into the tumultuous story of Patty Hearst's kidnapping and subsequent involvement with the Symbionese Liberation Army (SLA).
The book meticulously examines the events surrounding Hearst's abduction, her time in captivity, and her eventual participation in the SLA's criminal activities.
Toobin explores the complex psychological and social factors that may have influenced Hearst's transformation from heiress to revolutionary.
The narrative also covers the legal battles and public perception of the case, raising questions about guilt, coercion, and the nature of justice.
Through extensive research and interviews, Toobin provides a comprehensive account of one of the most sensational and perplexing episodes in American history.
#9706
• Mentioned in 4 episodes
Common Ground
A Turbulent Decade in the Lives of Three American Families
J. Anthony Lukas
Common Ground by J. Anthony Lukas is a Pulitzer Prize-winning book that chronicles the desegregation of Boston's public schools in the 1970s.
The book focuses on three families—the Twymons, an African-American family; the McGoffs, a white Irish-American family; and the Divers, a well-connected Brahmin family—and how they were affected by the court-mandated busing order.
Lukas explores the racial tensions, social upheaval, and political struggles that defined this period in Boston's history, offering a detailed and empathetic account of the human impact of these events.
#3861
• Mentioned in 9 episodes
Presumed Innocent
Scott Turow
In 'Presumed Innocent', Scott Turow crafts a suspenseful tale set in the fictional Kindle County.
The story follows Rožat 'Rusty' Sabich, a chief deputy prosecutor, who is assigned to investigate the murder of his colleague, Carolyn Polhemus.
Complicating the case is Rusty's past affair with Carolyn, which makes him a prime suspect.
The novel explores themes of legal intrigue, personal relationships, and the complexities of the justice system, all while maintaining a gripping narrative that keeps readers uncertain about the true culprit until the final pages.
John is joined by Jeffrey Toobin, celebrated author and legal analyst, who reflects on his extensive career in law and legal journalism. First, Jeffrey describes his legal background, including his clerkship on the Second Circuit which led to his years working for the Independent Counsel investigating the Iran Contra scandal (which led to his first book, Opening Arguments) and his years as an Assistant US Attorney. He also describes his years writing for the New Yorker and covering the OJ Simpson trial which led to his second book, The Run of His Life. Jeffrey then explains the writing process that has allowed him to complete nine books so far, including his strategy of writing about topics that have not been covered extensively by other authors, his absolute commitment to write 1,250 words per day for the project he is working on, and his habit of beginning to write each chapter in the middle and only writing the opening of the chapter later. John and Jeffrey then discuss why books on trials are so popular, including how trials are “perfect dramatic stages” and good trial lawyers are experts in both emphasizing the dramatic elements in stories and making issues interesting and meaningful to non-lawyers. Finally, John and Jeffrey discuss their favorite books about trial lawyers and personal insights into the most unforgettable lawyers Jeffrey has met including Johnnie Cochran, Barry Scheck, F. Lee Bailey and Justice Sandra Day O’Connor.
Podcast Link: Law-disrupted.fm
Host: John B. Quinn
Producer: Alexis Hyde
Music and Editing by: Alexander Rossi