
As was the case with millions of Americans in the spring of 2020, Eric Gleacher was looking for things to do when the pandemic took hold and the country lapsed into lockdown. He was unable to travel. Going out to dinner or visiting family and friends were non-starters. Golf was also out of the question. That was especially frustrating for a man as passionate about the game as Gleacher had long been.
So, he started thinking about other ways to occupy his time. Like writing a book.
“I had been considering that for a while,” explained the 81-year-old Gleacher, a former U.S. Marine infantry officer who went on to become one of the giants of the mergers and acquisitions business in the U.S. in the latter 20th century, as well as an elite amateur golfer. “I had experiences and ideas I thought might be interesting and of value to readers. Things about my times in the military, the successes I enjoyed in business and my involvement with the game of golf.
“But I procrastinated,” he added. “Then came the lockdown, and at that point, I determined it was now or never.”
So, Gleacher fired up his laptop. “I decided that I was going to work on the manuscript every day,” he explained. “It did not matter how much I wrote, only that I wrote. I had never kept a diary or made any notes. But I had good long-term memory, and I had stories I wanted to tell.”

He typed his first words in early March 2020 and was able to complete the manuscript by July. For help in the editing process, Gleacher turned to his son, Jimmy, who as a novelist and screenwriter knew his way around the English language. They self-published, and by April 2021, the first copies of the book were printed. Titled Risk. Reward. Repeat., it is part personal memoir, part business treatise and part guide to smarter living. And I found the book to be as entertaining as it was enlightening.
Success requires risk, Gleacher advises. But risk that stands “firmly on the platform of integrity.” Reward is inspired by integrity. That leads to being generous to those who have helped a person succeed. As for generosity, it fuels repetition and assists others as they forge their own way.
Interspersed with those tenets are stories of Gleacher’s life: a childhood that he describes as being “profoundly isolated” as the only child attending 10 different schools; his stint in the Marines; earning degrees at Northwestern University and the University of Chicago Booth School of Business; and then embarking on an uber-successful investment banking career that took him to Lehman Brothers and Morgan Stanley before he founded a boutique firm, Gleacher Partners.
Then, there are his times in golf, which he first played as a 12-year-old with his father Joe on a nine-hole course near Blair, Nebraska. Today, Gleacher is a member at some of the most prestigious clubs in the country – Seminole, Shinnecock Hills and the National Golf Links of America to name a few – and has won a total of 27 club championships at those and other retreats. He has also recorded eight holes-in-one and competed in several USGA and R&A championships. He even held for a spell the scoring record for a mini golf course on Hayman Island in Australia. And Gleacher remains quite proud of an inter-service golf championship he captured on Parris Island in 1965 while still a Marine.
One of his favorite playing partners is fellow Northwestern alumnus Luke Donald, and Gleacher has happily rubbed elbows with other greats in the game, such as Arnold Palmer, Sir Nick Faldo and Ben Crenshaw. He is first and foremost a competitor, and the ex-Marine gets damn near dewy-eyed when he talks about the thrills of playing tournaments on the game’s most historic and traditional courses, like the Old in St Andrews. But the man loves a casual game of golf, too. And especially loves teeing it up with his wife, Paula, who is a very accomplished player in her own right.
“One of things I learned was the importance of what I call flawless integrity.” – Eric Gleacher
“I shoot my age most of the time,” explained Gleacher, who is the father of six children and also has two step kids and eight grandchildren. “But while my ball striking was once my greatest strength, I rely more and more on my short game. That’s where I am at my best.”
Gleacher has also taken on significant roles in golf governance, as secretary of the USGA and a member of its Executive Committee. He was also among the strongest advocates for bringing the U.S. Open to Bethpage Black in 2002. And as an expert on the rules of golf, Gleacher has officiated in 17 major championships.
Among my favorite parts of the book are his tales of being a Marine and what the Corps taught him.
“One of things I learned was the importance of what I call flawless integrity,” explained Gleacher, whose father was not only a professional boxer for a spell but also a combat veteran of World War II. “If you are 23 years old and taking over a rifle platoon, you have got to figure it out pretty quick. You have troops who are young, who are mostly from the inner city and who do not have a high school graduation. But they are very intuitive. They have great instincts. And you would lose them in an instant if you tried to BS them.”

“It is often life and death in the military,” added Gleacher, who enlisted in the Corps after graduating from Northwestern and then enrolled in business school at the University of Chicago once he was discharged. “So, to survive and to properly lead you have to have flawless integrity. And that is also something that I brought with me when I went to work on Wall Street, a place that is not exactly known for its integrity. It also played a big role in my life in golf and even deepened my understanding of what that concept is all about. In both cases, I wanted very badly to succeed and to win. But only by doing it right and playing by the rules.”
I was also enthralled by Gleacher’s commitment to paying it forward and the ways this very successful man continues to give back as he urges others to do the same. The fact that all profits from his book are going to charity shows that he practices what he preaches. But there are many other examples, such as the Veterans Scholarship Fund he established some years ago at the University of Chicago’s Booth School with a $10 million donation. And the $15 million he put forth for that institution’s Gleacher Business Center School campus off North Michigan Avenue on the Chicago River. It was also Gleacher who financed the building of the indoor practice and training facility at Northwestern University in 1998 – and who gave another $7 million to have that center redesigned and enlarged last year. And he also provided the money so Western Illinois, the school he had attended before transferring to Northwestern, could expand its nine-hole course to a full 18.
At his urging, the university named the revamped course at Western Illinois after Gleacher’s old golf coach, Harry Mussatto, a man whom he reveres to this day for all he did for him.
Risk. Reward. Repeat. For Eric Gleacher, that is what it is all about.
To order copies of the book, go to: geni.us/RiskRewardRepeat.