Jed S. Rakoff

• 1. Introduction

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  Jed S. Rakoff keeps a baseball signed by Mariano Rivera in a glass case on his desk. It is a small, telling detail about a man who has spent decades presiding over some of the most consequential legal battles in American life. He has ruled the federal death penalty unconstitutional, blocked major Wall Street settlements, ordered the Pentagon to release Guantanamo detainee records, and sentenced the man who mailed pipe bombs to former presidents. He has done all of this from the U.S. District Court for the Southern District of New York, where he has served since 1996. Who is Jed Rakoff, and how did a kid from Germantown, Philadelphia, become what Rolling Stone called "a sort of legal hero of our time"? The answers run through Oxford, Harvard, seven years as a federal prosecutor, and a judicial philosophy built on impatience with delay, deference, and deals that protect the powerful at the expense of everyone else.

• 2. From Philadelphia to the Bench

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  Rakoff was born in Philadelphia on the 1st of August 1943, and grew up in the Germantown section of the city, attending Central High School. At Swarthmore College, where he earned his Bachelor of Arts in English literature in 1964, he was student council president and editor-in-chief of the newspaper. He then crossed the Atlantic for a Master of Philosophy in Indian history at Balliol College, Oxford, in 1966. His legal training came at Harvard Law School, where he graduated cum laude in 1969 as a member of the Harvard Legal Aid Bureau.

  His first job out of law school was clerking for Judge Abraham Lincoln Freedman of the U.S. Court of Appeals for the Third Circuit, a post he held from 1969 to 1970. Two years of private practice at Debevoise and Plimpton followed before he joined the U.S. Attorney's Office for the Southern District of New York as a federal prosecutor. He spent seven years there, finishing as Chief of the Business and Securities Fraud Prosecutions Unit. That experience left a permanent mark. His famous description of the federal mail fraud statute captures the affection prosecutors develop for their sharpest tool. He called it "our Stradivarius, our Colt .45, our Louisville Slugger, our Cuisinart and our true love."

  After leaving the government, he returned to private practice at Mudge, Rose, Guthrie, Alexander and Ferdon from 1980 to 1990, then at Fried, Frank, Harris, Shriver and Jacobson from 1990 to 1996, heading the criminal defense and civil RICO sections at both firms. President Bill Clinton nominated him to the Southern District bench on the 11th of October 1995. The Senate confirmed him on December 29 of that year, and he entered duty on the 1st of March 1996.

• 3. A Judge Who Moves Fast

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  Rakoff assumed senior status on the 31st of December 2010, a status that typically signals a lighter docket. He has continued to take a full load of cases regardless. That drive for speed is not impatience for its own sake. Having seen from inside private practice how delays and procedural gamesmanship made the American legal system unaffordable for ordinary people, he concluded that tolerating such tactics carried a cost. "The price of being a nice guy is too high, much too high, in terms of the system of justice," he said.

  His clerkship pipeline reflects how seriously the legal world takes his chambers. From 2011 to 2015, he sent more clerks to the U.S. Supreme Court than any other district court judge in the country. He has also sat regularly by designation on the U.S. Court of Appeals for the Second Circuit throughout his career, and since 2011 has regularly sat on the Ninth Circuit as well, occasionally joining the Third Circuit and several federal district courts in California, Florida, and Oklahoma.

  Outside the courtroom, Rakoff has taught criminal law and white-collar crime at Columbia Law School since 1988. He also teaches at NYU Law School and runs annual seminars at the University of California, Berkeley, and the University of Virginia. He was elected to the American Law Institute in 2009 and to the American Academy of Arts and Sciences in 2013. His work on forensic science included serving on the National Commission on Forensic Science from 2013 to 2017 and co-chairing the National Academies of Science's Committee on Eyewitness Identification. He has helped train foreign judges in more than a dozen countries, from Azerbaijan to Turkey.

• 4. Confronting the Death Penalty

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  In 2002, Rakoff declared the federal death penalty unconstitutional in United States v. Quinones. His reasoning was stark. He wrote that innocent people were being sentenced to death with greater frequency than previously understood, and that proof of their innocence often did not surface until long after conviction. He concluded that executing such people was not merely a risk but "fully foreseeable," and that it violated both procedural and substantive due process. The New York Times called his ruling "a cogent, powerful argument that all members of Congress, indeed all Americans, should contemplate."

  Rakoff later said he had suspected the ruling would be reversed. He knew a majority of the Second Circuit would read the Supreme Court's decision in Herrera v. Collins differently than he had. He was right. The Second Circuit reversed him, in United States v. Quinones, 313 F.3d 49, decided in 2002. Still, the opinion itself endured as a serious constitutional argument, even if it could not bind the courts that reviewed it.

  The case captured what has defined Rakoff's bench: a willingness to reach a conclusion that the law, fairly read, seems to demand, even when reversal is probable. That same quality would surface again and again in the decades that followed, from Wall Street settlements to immigration enforcement to the Epstein litigation.

• 5. Taking On Wall Street

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  The Securities and Exchange Commission had a long-established practice of settling corporate fraud cases without requiring companies to admit or deny wrongdoing. Rakoff found that practice inadequate on at least two occasions that drew national attention.

  In August 2009, Bank of America agreed to pay the SEC a $33 million fine over its failure to disclose an agreement to pay up to $5.8 billion in bonuses at Merrill Lynch. Rakoff refused to approve the deal on August 5. He then rejected it outright on September 14, writing that the consent judgment looked like "a contrivance designed to provide the S.E.C. with the facade of enforcement and the management of the Bank with a quick resolution of an embarrassing inquiry, all at the expense of the sole alleged victims, the shareholders." He cited Oscar Wilde on cynicism, quoting Lady Windermere's Fan. He forced the parties to return with a fuller account of what happened and a higher penalty, then reluctantly approved the revised settlement, calling it "half-baked justice at best" and quoting "the great American philosopher Yogi Berra" in the ruling.

  Two years later, Rakoff rejected a $285 million settlement between Citigroup and the SEC. He wrote that the agency's longstanding policy of allowing defendants to settle without admitting wrongdoing was "hallowed by history, but not by reason" and deprived the court of any factual basis for the relief it was being asked to impose. The Second Circuit vacated his decision in June 2014, finding that he had shown too little deference to the SEC. Circuit Judge Rosemary Pooler wrote for a unanimous panel that Rakoff had overstepped his authority.

  In the WorldCom accounting fraud suit, Rakoff approved a settlement on the 7th of July 2003, and appointed former SEC chair Richard C. Breeden as Corporate Monitor. Breeden prepared a report titled "Restoring Trust" proposing wide corporate governance reforms. Rakoff later credited Breeden with helping to transform a fraud-ridden company into what became MCI, Inc., which Verizon purchased in January 2006.

• 6. Landmark Criminal Cases

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  United States v. Gupta, decided in 2012, brought Rakoff into the center of the biggest insider trading prosecution in a generation. Rajat Gupta, the former managing partner of McKinsey and a board member of Goldman Sachs and Procter and Gamble, was accused of leaking confidential board information to hedge-fund billionaire Raj Rajaratnam of the Galleon Group. The trial showed that within a minute of finishing a Goldman Sachs board teleconference about Warren Buffett's $5 billion investment in the bank, Gupta called Rajaratnam. Minutes later, Rajaratnam ordered traders to buy as much as $40 million in Goldman Sachs stock. The jury convicted Gupta on three counts of securities fraud and one count of conspiracy. Rakoff sentenced him to two years, saying his crime was "an egregious breach of trust."

  Three years later, while sitting by designation on the Ninth Circuit, Rakoff created a deliberate circuit split with the Second Circuit over what constitutes insider trading in United States v. Salman. He held that an insider who disclosed confidential information to a relative without receiving anything in return was guilty of insider trading, contradicting the Second Circuit's narrower standard set in United States v. Newman. The Supreme Court granted certiorari and unanimously affirmed Rakoff's Ninth Circuit opinion in 2016, overturning the Second Circuit's conflicting doctrine. Legal observers described the episode as "the stuff of legend" and "delicious irony."

  In August 2019, Rakoff sentenced Cesar Sayoc to 20 years in prison for the October 2018 mail bombing attempts. Sayoc had sent improvised explosive devices to more than a dozen critics of President Donald Trump, including former presidents, former vice presidents, senators, and private citizens. Sayoc pleaded guilty to 65 felony counts. Rakoff said that no one could pretend the sentence was not substantial punishment, "but in the Court's view, it is no more, and no less, than he deserves."

• 7. Science, Youth, and Criminal Justice

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  Rakoff's long engagement with neuroscience and forensic science has shaped some of his most cited opinions. He co-edited The Judge's Guide to Neuroscience and participated in drafting the third and fourth editions of the federal judiciary's Manual on Scientific Evidence. His interest in how science should inform legal judgment runs through his academic work and his rulings.

  In 2021, Rakoff granted a sentence reduction to Andrew Ramsay, who had been convicted of murder in connection with a 1992 Labor Day block party shooting in the Bronx. Ramsay was 18 years old at the time of the crime. Under the First Step Act, Rakoff reduced his sentence from life imprisonment to 30 years. The opinion explored why youth matters in sentencing, drawing on neuroscientific, psychological, and sociological research about adolescent immaturity, susceptibility to peer influence, and capacity for rehabilitation. Adolescents' irresponsible conduct, Rakoff wrote, "is not as morally reprehensible as that of an adult." The opinion has since been cited by more than 80 federal courts.

  Rakoff has applied similar skepticism about sentencing to white-collar defendants. In United States v. Adelson, he confronted a statutory maximum sentence for a securities fraud conviction that would have kept a 40-year-old man in prison until the age of 125. He called this "barbarity" and sentenced Richard Adelson to three and a half years, plus $50 million in restitution, noting that even federal prosecutors had "blinked" at what the guidelines produced. His view is that when the Sentencing Guidelines produce results that are "patently absurd on their face," a court must rely on the broader principles in federal sentencing law.

• 8. Beyond the Courtroom

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  Rakoff has written for the New York Review of Books regularly since 2014, published more than 200 articles, delivered more than 900 speeches, and produced several satirical poems. His book Why the Innocent Plead Guilty and the Guilty Go Free was published by Farrar, Straus and Giroux in 2021. In 2017, Pulitzer Prize-winning journalist Jessie Eisinger devoted two chapters of his book The Chickenshit Club to Rakoff, concluding that Rakoff had "cried out about the injustice of the criminal law system" and had "played a role to change the way the country addresses corporate criminals." Fortune listed him among the World's 50 Greatest Leaders in 2014. Reynolds Holding's 2025 book Better Judgment profiled him alongside two other judges.

  He has been married since 1974 to Dr. Ann R. Rakoff, a child development specialist. They have three daughters and three grandchildren, and their shared hobby is ballroom dancing. His younger brother Todd is a longtime professor at Harvard Law School. His older brother was murdered in 1985.

  On the 13th of April 2013, the Russian Ministry of Foreign Affairs placed Rakoff on a list of Americans banned from entering Russia, issued in direct response to the American Magnitsky list the day before. It was an unusual recognition for a federal district judge, and a measure of how far his rulings had traveled. His awards include the Federal Bar Council's Learned Hand Award for Excellence in Federal Jurisprudence in 2018, the American College of Trial Lawyers' Leon Silverman Award for Distinguished Public Service in 2021, and the World Jurist Association's Medal of Honor in 2023. The cryptocurrency case SEC v. Terraform, in which Rakoff held in 2024 that crypto tokens can be securities under U.S. law, settled for more than $4.5 billion in June 2024, and the question of whether his reasoning will hold across the courts remains open.