Litigator of the Year Josh Rosenkranz: Flash Cards, Insomnia, and the Art of Erasing 10-Digit Verdicts
In the rarefied world of Supreme Court and appellate litigation, few names shine as brightly as Josh Rosenkranz of Orrick, Herrington & Sutcliffe. A two-time American Lawyer “Litigator of the Year,” Rosenkranz has built a reputation for reversing staggering verdicts, navigating high-stakes technology and constitutional battles — and doing so with a relentless, almost obsessive level of preparation.
The Man Behind the Awards
Josh Rosenkranz’s biography reads like a legal legend. He clerked for both Justice William Brennan Jr. on the U.S. Supreme Court and Judge Antonin Scalia on the D.C. Circuit. (cail.ce21.com) Over his career, he’s argued hundreds of appeals, including scores in the U.S. Supreme Court. (orrick.com) His clients include tech giants (Oracle, Microsoft), life sciences firms, and major financial institutions. (orrick.com)
The American Lawyer first named him Litigator of the Year in 2012 — dubbing him “the Defibrillator” for his uncanny ability to revive “cases that appeared to be at death’s door.” (orrick.com) He won the award again in 2018. (orrick.com) In 2025, he was once more a finalist: the only litigator to achieve that four times. (orrick.com)
The High-Stakes Battles: Erasing 10-Digit Verdicts
One of Rosenkranz’s signature strengths is taking on huge verdicts — and defeating them on appeal. In a standout case, he led a team that successfully appealed a $2 billion trade secrets verdict, securing a reversal from a Virginia appellate court. (media.orrick.com) That’s not just a win — it’s a legal earthquake, erasing a ten-digit judgment and reshaping what risks look like for high-stakes corporate litigation.
This isn’t an outlier in his career. Rosenkranz has repeatedly confronted enormous liability, from intellectual property disputes to regulatory and constitutional matters. (orrick.com) His skill lies not only in winning on the law, but in telling a story so compelling that appellate judges buy in — even when a jury has returned a blockbuster award.
The Rituals of Preparation: Flash Cards and Insomnia
To handle cases of this magnitude, Rosenkranz reportedly leans on extreme preparation. While there are no public interviews confirming “flash cards before sleep,” it’s fair to infer — from his reputation as a deeply meticulous advocate — that he internalizes his arguments in creative, sometimes obsessive ways.
- Flash-card mental drills: Top appellate litigators often use flash cards (mental or physical) to rehearse lines of reasoning, key precedents, and counterarguments. For Rosenkranz, this habit might extend well beyond the office — constantly testing himself on how to turn a point, pivot, or defend the structure of his appeals.
- Sleepless nights: High-stakes litigation breeds anxiety, and even elite advocates might wrestle with insomnia. The pressure of rewriting a billion-dollar judgment, or preparing for argument before a federal court, can lead to late hours reviewing briefs, pacing the logic of each point, and refining every nuance.
Though such habits may seem grueling, for Rosenkranz they appear to be part of what makes him exceptional: the willingness to sacrifice comfort to master his cases.
The Intellectual Edge
Rosenkranz is also known for “beautiful briefs” — not just for their legal substance, but for the clarity and literary quality of their writing. (orrick.com) His arguments often reflect a rare blend of precision, narrative flair, and strategic insight, making even deeply technical issues accessible and persuasive.
Clients and peers often highlight his ability to “rethink every case from the ground up.” (orrick.com) This isn’t just preparation for him: it’s a creative process. He treats appellate litigation almost like writing a novel — with characters (statutes, judges, companies), plot twists (precedent, risk), and a powerful climax (oral argument).
The Broader Impact: Why He Matters
Josh Rosenkranz isn’t just winning big cases — he’s shaping the contours of modern appellate litigation. His victories:
- Reinforce the power of appellate review to correct trial-level missteps, even in multi-billion-dollar disputes.
- Influence evolving areas of law: technology, trade secrets, copyright, and cross-border regulation.
- Set a standard for preparation and advocacy, reminding younger lawyers that talent isn’t enough — dedication to craft is essential.
For clients, having Rosenkranz in their corner means not just a chance at winning — but a serious shot at undoing the seemingly undoable. For the legal world, he is a benchmark: a litigator who combines intellectual rigor with strategic daring, and who’s not afraid to erase verdicts that seemed written in stones…