The playbook for the defining moments every leader encounters

Takeaways from billion-dollar bankruptcies (and the ones that didn't happen) teach you how to navigate high-stakes business crises where no solution is perfect. It comes down to genuine relationships, creative problem-solving, and being unafraid to run into the burning building.

About the Book

Jamie Sprayregen built the world’s largest restructuring practice from scratch at Kirkland & Ellis, co-headed Goldman Sachs’s Restructuring Group, taught corporate restructuring at Wharton, and earned recognition from Chambers & Partners as “the Mick Jagger of the bankruptcy bar.” Now the co-head of Capital Solutions & Restructuring at the global law firm Paul, Weiss, Rifkind, Wharton & Garrison LLP, Sprayregen draws on his singular career to share the principles that drove his success—and that anyone can use to drive theirs. 

The Upside of Downside takes readers inside some of the most notable corporate bankruptcies in history. By sharing lessons learned from his work on cases involving the City of Detroit, United Airlines, Toys “R” Us, Caesars, and others, including some of the biggest deals that didn’t happen thanks to timely and creative problem solving, Sprayregen reveals how billion-dollar crises demand rapid decision-making and relentless preparation. 

Each story illustrates a distinct principle—from “scarcity sells” to “your big moment will come before you’re ready”—grounded in real outcomes rather than abstract theory. Beyond the stories themselves, this book packages Sprayregen’s insights into a series of career lessons. Rather than offering broad business platitudes, it addresses the particular challenges of building a practice within complex organizations: winning trust under pressure, cultivating client relationships during chaos, and turning adversity into competitive advantage. These are the same lessons Sprayregen has shared with colleagues and mentees throughout his career, refined over decades of high-stakes dealmaking. 

Lawyers, bankers, consultants, board members, c-suite executives, and other leaders—whether early-career or more seasoned—will find in The Upside of Downside a rare combination of gripping narrative and directly applicable guidance. The playbook here is informed by decades of navigating billion-dollar crises and translates to any role where judgment, resilience, and the ability to perform under pressure determine success. Readers will close this book with a renewed confidence that even the hardest situations can become a foundation for achievement. There is upside in even the most challenging struggles.

“Jamie Sprayregen has spent four decades navigating some of the world’s largest and most complex corporate restructurings. In The Upside of Downside, he shows what sound judgment requires when the facts are incomplete, interests collide, and the choice is often not between good and bad, but between bad and worse. Important lessons for anyone responsible for consequential decisions.”

— Ken Griffin, CEO, Citadel

“I can make the case that the greatest strength of our economic system is less that it leads inexorably to the best decisions, but rather that it efficiently and fairly resolves mistakes so that capital and talent can be redeployed for growth. Easy to say, hard to accomplish. The ultimate arena is the bankruptcy process, which is Jamie's home court, and where the stakes and emotions run highest. His 'dispatches' will reward the reader with an understanding that most business people don't think about until it's the only thing that matters.”

— Lloyd Blankfein, Former Chairman and CEO, Goldman Sachs

“As an entrepreneur, I know that success and failure are often two sides of the same coin. Jamie is one of the best at making sense of each, given his decades of experience navigating failure and steering companies that seemed to have no way out. This book reveals the strategic acumen that has made him a global leader, offering advice that isn't just for lawyers but for anyone seeking mastery of risk and reward.”

— Brad Keywell, 2019 EY World Entrepreneur of the Year, co-founder of Groupon and many other companies

“Throughout my career, I’ve been a lender to dozens of companies and have seen advisors help navigate their clients through complex restructurings. No one has advised companies better than Jamie, and his stories and lessons are extremely insightful and perfect to help the next generation learn how to follow in his footsteps and deliver exceptional service and results in very challenging situations.”

—Norma Corio, Former JPMorgan Treasurer, Investment Banker, and Head of Restructuring

“Jamie Sprayregen is the greatest bankruptcy dealmaker of the past generation, and he created and led the top restructuring law practice in the world. This alone would make The Upside of Downside essential reading for anyone interested in modern American business history. It’s a book you can read in a single sitting, and a book that may stay with you for a lifetime.”

—David Skeel, author of Debt’s Dominion: A History of Bankruptcy Law in America and Professor, University of Pennsylvania Carey Law School

About the Author

JAMES H. M. SPRAYREGEN is the Co-Head of Capital Solutions & Restructuring at the global law firm Paul, Weiss, Rifkind, Wharton & Garrison LLP. He founded Kirkland & Ellis’s worldwide Restructuring Group in 1990 and later served as co-head of Goldman Sachs’s Restructuring Group, Vice Chairman of Global Strategy and Growth at Hilco Global, and Adjunct Full Professor of Finance at The Wharton School of the University of Pennsylvania. Chambers and Partners has called him a “bankruptcy guru” and “the Mick Jagger of the bankruptcy bar.” The National Law Journal named him one of “The Decade’s Most Influential Lawyers” in 2010, and he is a member of the Turnaround Management Association’s Industry Hall of Fame.

James has partnered with Worthy Books, a 501(c)3 nonprofit organization, to share his lessons on how to navigate high-stakes business decisions to universities and public libraries across the country.