Praise from clients, colleagues, adversaries, and thought leaders around the world
“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
“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
“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. But rather than simply recount his rise, Sprayregen distills ten often-surprising leadership and career advancement lessons from his decades in the elite turnaround business, illustrating them with unforgettable stories and with pithy quotes from his hero Winston Churchill, himself, and others. 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
“Jamie Sprayregen is the most accomplished corporate restructuring attorney ever. Jamie is to corporate reorganizations what Hank Williams was to country music; what Bach was to classical music; what Babe Ruth was to baseball; what Michael Jordan was to basketball. I only wish I’d had The Upside of Downside to read when I was a young, aspiring corporate reorganization attorney. It is a veritable how-to manual on striving for, building, and achieving professional success beyond all imagination, doing so with integrity, treating others well, and having a blast all along the way. I will be recommending
The Upside of Downside as required reading for all of my students. And for future academics studying the history of corporate reorganizations—25, 50, 100 years from now—The Upside of Downside is a riveting ethnography from the central figure in the corporate reorganization ecosystem of this era.”
—Ralph Brubaker, Professor, University of Illinois College of Law
“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
“My business partner, Bill Grube, and I were Jamie’s very first client. Early on, I wrote a letter to Kirkland’s managing partner saying his fee was too low—and that Jamie was a special case who needed to make partner quickly. Forty years later, I’m fortunate to still call myself both a client and a friend. Over that time, I’ve developed tremendous respect for Jamie, not only for the professional he is but for the person he is. Now I can add ‘author’ to that. Jamie has taken the wisdom and perspective that come from a lifetime of experience and put them into a book that has something to teach all of us. There are lessons here about failure, certainly—but even more importantly, about what we do with success.”
—Fred Fehsenfeld, Builder of one of the more remarkable multi-generational family businesses in America and also, by design, someone you've probably never heard of
“I had the good fortune of meeting the young Jamie Sprayregen in 1990, and I am honored to have had the opportunity to mentor Jamie all along his career journey. I can tell you that Jamie’s book recounts the extraordinary way in which he helped to shape the modern bankruptcy/restructuring world and is a true guide on how to be super successful in building a career and a business even in the face of adversity.”
—Jack S. Levin, Semi-retired senior partner, Kirkland & Ellis, and one of the founders of the PE/VE legal business
“Private equity and sports are all about winning... and losing. The lessons we all need to absorb are in many ways no different from what restructuring professionals like Jamie navigate every day. I’m sharing this book with everyone on my teams, both in the PE world and on the field!”
—Justin Ishbia, Founder and Managing Partner, Shore Capital Partners
“In
The Upside of Downside, Jamie Sprayregan highlights key principles for achieving success and turning failure into a positive outcome: being honest with yourself, being truthful with your team and counterparts, and always keeping your word to friends and adversaries alike. As you navigate life and business, self-honesty helps prevent repeating the mistakes that lead to failure. By staying truthful and dependable, you earn respect and demonstrate that you are a trusted partner. reflects the journey Jamie and I shared. His team represented United Airlines in one of the most complex bankruptcies in history. In contrast, my team represented tens of thousands of Machinists Union members on the other side of the table. Ultimately, we achieved what many thought impossible. In the end, we gained mutual respect and a relationship that has lasted far beyond the negotiation table.”
—Robert Roach, Former Vice President of Transportation for the Machinists Union
“Jamie and his team were essential contributors to the success of the United Airlines restructuring and eventual merger with Continental Airlines. His role—as the content of this book attests—extended well beyond legal counsel, into strategy deliberations and decisions with the management team and into the boardroom. It is difficult to imagine, upon reflection, the subsequent success of United Airlines without Jamie and the vital role he played during its most challenging period.”
—Glenn Tilton, Former Chairman and CEO, United Airlines, Inc.
“What Jamie teaches is not slogans. It is forty years of practiced judgment: dignity of process when the stakes are ugly, and mastery of chaos when nobody has a clean answer. Dealmakers will recognize the real work, and we are all better for having this written down.”
—Michael Silverton, Head of Macquarie Capital
“Political and even geopolitical negotiation is in many ways not so dissimilar from a restructuring situation.There are emotions bound together with substantive realities, much at stake for all parties, and lots of ways to compromise, win, and lose. The lessons Jamie shares in this book are by no means limited to the bankruptcy arena. There is tremendous value here in many domains.”
—David Friedman, Former US Ambassador to Israel and former Restructuring Lawyer
“I have benefited from Jamie’s wisdom, kindness and friendship since he helped us complete a successful restructuring of the United Artists and Regal cinema companies over 25 years ago. I have never met anyone who works so intentionally to deliver extraordinary personalized client service and develop creative settlement strategies within a very complicated area of law, before the uncertainties of the bankruptcy court room result in higher fees and a less favorable outcome. This book is typical Jamie… completely transparent and unselfish about sharing his wisdom with the next generation, and should be required reading for anyone in business or young people thinking about a law or investment banking career. There is no one that I would rather have by my side.”
—Kurt Hall, Former Co-CEO of Regal Entertainment Group (and former CEO of United Artists Theatres)
“I’ll never forget that during one of the toughest moments of an incredibly difficult restructuring, Jamie told me, ‘Sometimes you have to have a little shattered glass along the way... and then fix it.’ That stayed with me ever since. Jamie’s perspective, judgment, and ability to remain calm and provide top-notch judgment when things were at their most challenging had a real impact on me—and are sure to have an impact on readers.”
—Alan Leibman, Longtime friend and business associate, Former CEO Kerzner, Paradise Island and One and Only Hotel Group
“I’ve watched Jamie Sprayregen from the other side of the table as well as having had the privilege of being his client. A legend in the industry, Sprayregen has stories and lessons that can help and inspire everyone from the most junior level on up to senior advisors, business people, and investors.”
—Ed Mulé, CEO of Silver Point Capitol
“I have known Jamie for nearly forty years and watched him build the most formidable restructuring practice in the world. This book finally reveals how he did it: with judgment, with relationships, and with a stubborn decency toward people on every side of the table. He asks, ‘compared to what?’ There is nothing else like it.”
—Reeve B. Waud, Founder, Chairman and CEO, Waud Capital Partners; Founding Chairman, Acadia Healthcare
“As a C-level executive for a company that went through a restructuring, I relied on Jamie for sharp counsel and creative solutions. This book gives readers exactly what I got when I hired him: wisdom, judgment, ethics, and mastery. It’s a must-read.”
—Danielle Hunter, Experienced C-Suite executive and independent public company board member
“Jamie Sprayregen is a master of his profession, and there is no one more suited to tell the story of American bankruptcy—not to mention the avoidance of it and recovery from it—than him. This book contains valuable business and leadership lessons for lawyers and non-lawyers alike, and demonstrates why companies have turned to Jamie again and again over the past four decades.”
—John Quinn, Founder and chairman of Quinn Emanuel, a 1300-lawyer global litigation firm
“As a private equity investor and board member of many companies over the course of my career, I have seen failure and potential in many forms. The one constant is you need an experienced and wise hand to help you avoid it. That person is Jamie Sprayregen, and this book is testament to his skills and wisdom.”
—John Canning, Former Chairman/CEO of Madison Dearborn Partners
“This book is classic Jamie: applying lessons learned from years of the intense practice of bankruptcy law to life in general. He has truly mastered the art of common sense.”
—Paul Finnegan, Co-founder and Chairman, Madison Dearborn Partners
“In business, politics, and life, the problems you encounter are rarely just about the issues on the surface. Success requires understanding the people involved and an ability to navigate the complex dynamics and tensions that sit beneath the surface. Jamie gets that, and his deep appreciation for what it takes to build and sustain relationships jumps off the pages of The Upside of Downside. Anyone in a role where they need to work effectively with others—which is to say, everyone—will find something of real value in these pages.”
—Tom Wyler, Partner, Hakluyt & Co., global advisory firm
“I've known Jamie for most of his career, and he’s a formidable adversary and a towering figure in his field. He writes the same way that he negotiates: candidly and without pretense. In the world of restructuring, there's often no good answer, but he always searches for the least bad answer. The Upside of Downside offers a trenchant reminder that the people who understand failure best also know how to build things that last.”
—D.J. (“Jan”) Baker, Retired partner and and former Co-Chair of the Restructuring Practice, Latham & Watkins LLP
"Strategic vision is what sets Jamie apart from most restructuring professionals. That vision is a result of his own intelligence, listening to others, soliciting ideas, a constant desire to learn, a willingness to make decisions, and the sole agenda of obtaining the best result. Over 40 years, Jamie has not changed. Clients find comfort in his endless desire to stay focused and find the best possible solution for the situation, no matter how much effort is involved. This book is Jamie sharing, as he often does, what he has learned and the best ways to apply that knowledge to obtain an optimal result. A must read."
—Laura Davis Jones, Partner, Pachulski Stang Ziehl & Jones LLP
“Jamie Sprayregen has spent forty years running into burning buildings the rest of us would happily avoid. This book is what he carried out. For anyone who leads a business, sits on a board, or deploys capital, it is the most useful account I have read of how failure actually works, and how to keep it from happening to you.”
—Mark Morris, Former CFO of Seadrill Ltd and CEO of Seadrill Partners LLC
“I give Jamie a huge amount of credit for distilling his stories into principles that can help drive the success of others. The Upside of Downside is useful, smart, and powerful.”
—Kent Zimmerman, Co-chair, Zeughauser Group, a leading international management consultancy to law firm leaders on M&A
“The greatest perk of being a young partner at Kirkland & Ellis was the opportunity to learn from Jamie Sprayregen. Not just about practicing law, but about exercising judgment, earning trust, and helping people find a way forward when the easy answers have run out. I was fortunate to have that education firsthand. I’m delighted that, with this book, others can now learn from him, too.”
—Jonathan Friedland, Publisher, The National Law Review, former partner, Kirkland & Ellis, LLP, and practicing attorney.
International
“Jamie Sprayregen has given us a fascinating account of his professional life working at the highest levels as an insolvency and restructuring lawyer. And woven into this collection of stories are many invaluable life lessons drawn from the wellspring of a lifetime working with corporate failures. He reminds us that failure is not necessarily terminal and that a calm head and a good measure of common sense will often lead to possibilities that were dismissed in the heat of emotion.”
—Sundaresh Menon, Chief Justice of Singapore
“Jamie, a leading light in our profession, has seen some failures, but also a lot of success. In Singapore, we know him as a lawyer with great judgment who can step in to help companies at their moments of greatest vulnerability. It is hard to recommend a book, and a professional, more strongly.”
—Nicky Tan, Renowned Singapore-based mega-company turnaround professional
“Jamie is the only US bankruptcy lawyer with a reputation in Australia bigger than Texas. We Aussies, and our ultra conservative bankruptcy laws, emanate from our convict past. Jamie influenced a sea change in the Australian bankruptcy profession from failure to turn around and restructuring. The Upside of Downside is brilliant reading that demonstrates the why and how and I couldn’t put it down. I’m proud to give it my highest recommendation.”
—Leon Zwier, 2025 ‘lawyer of the year’ for insolvency and reorganisation law
“Few people have spent as much time at the scene of major corporate crises as Jamie Sprayregen. In The Upside of Downside, he turns four decades of experience in some of the world’s largest and most complex restructurings into an engaging account of judgment under pressure—how to negotiate, lead, make difficult choices, recover from mistakes, and, above all, learn from failure. The stories are fascinating; the lessons apply far beyond bankruptcy.”
—Weijian Shan, Executive Chairman and Co-Founder, PAG (a leading Asia-based private equity firm)
“Sometimes, in life and in business, we experience serious failures that don’t fully mature until later. This is especially true in bankruptcy, but learning from failure is not limited to this sphere. What is most exceptional about The Upside of Downside is that the stories apply far beyond the legal world, far beyond the business world. We can all take something valuable from this book in lessons for life and career development.”
—Hideyuki Sakai, Executive Chairman and Co-Founder of Sakai & Mimura, later Bingham McCutchen Tokyo until its merger with Anderson Mori & Tomotsune
“The Upside of Downside contains the operating principles of a man who has seen more companies fail, and saved more of them, than anyone I know. His profound suggestions from his difficult but successful experiences as a leading bankruptcy lawyer are inspiring to me and will inspire readers.”
—Eiji Katayama, Former Trustee of Japan Airlines
“Honesty, judgment, and trust are what I think of when I think about Jamie Sprayregen. He understands how you practice law with integrity and how you build a sustainable legal business. The Upside of Downside explains why he has built relationships and effectively served companies and individuals across the globe.”
—Zia Mody, Co-Founder and Managing Partner of the Pan India Law Firm AZB & Partners, on Fortune India’s 100 Most Powerful Women list for the past 15 years
“In India, there are not many US lawyers who have earned the same kind of respect as Jamie Sprayregen. I’ve known him for decades as a true counterpart, a top professional with extreme judgment, work ethic, and wisdom to share with the world.”
—Cyril Shroff, Founder and managing partner of Cyril Amarchand Mangaldas, India’s largest law firm
“As someone who worked on drafting India’s new bankruptcy code, I must say, we owe a great deal to Jamie Sprayregen and the inspiration his decades of work has provided. He is a legend in the field and his book encapsulates so much of what has made him great and has tremendous lessons for practitioners and business persons.”
—Bahram Vakil, Founding Partner, AZB & Partners
“The Upside of Downside distills four decades of frontline dealmaking into hard-won wisdom from America’s biggest bankruptcies. Jamie Sprayregen—the giant in the field—provides essential and inspiring lessons for generations of practitioners on how to turn catastrophe into opportunity.”
—Sumant Batra, President, Insolvency Law Academy, India
“Walking into a room with Jamie on our team always gave us the best chance for a solution. His presence in the room always meant we were able to be heard and respected. Jamie’s ability to open doors in the highest echelons of business could have only occurred because of the high regard and trust he had earned during his long and successful career. During the bankruptcy of Lehman, we were often at odds with our counterparts across borders but with Jamie’s deep understanding of the different laws and protocols across different jurisdictions, we were guided to win-win solutions across a minefield of conflicting creditor interests. Jamie’s calmness and astute thinking in difficult and tense discussions was often the difference between a result and failure. This book encapsulates the power of being trusted and having real relationships amongst peers, which is the base of the success of Jamie’s career. It provides wonderful lessons for readers of this book to aspire to.”
—Stephen Parbery, Longstanding chairman of the leading Australian restructuring firm, PPB Advisory, a veteran of many of Australia’s major corporate insolvencies, and termed an “insolvency industry doyen”
“Late at a Zurich hotel bar, immersed in a discussion about medieval Persia and today’s conflicts, it almost escapes you that the man opposite you is ‘Mr. Bankruptcy.’ It is Jamie’s intellectually profound yet humble curiosity about people and the world that makes him so captivating—and, as the reading reveals, contributes greatly to his professional success.”
—Frank Nikolaus, Restructuring investor, former insolvency administrator, and longtime president of TMA Germany

