Cigar Aficionado

Hanging near the center of all the memorabilia that decorates and accentuates Jimmy Dunne’s office in midtown Manhattan is a small, framed piece with the words “Jimmy’s Motto” written as a headline. “Every morning in Africa a zebra wakes up and knows it must outrun the fastest lion or it will be killed,” it reads. “Every morning the lion wakes up and knows it must outrun the slowest zebra or it will starve. It doesn’t matter whether you’re a lion or a zebra, when the sun comes up you better be running!”

There is an accompanying photo of a zebra chasing a lion. The zebra is labeled “Sandler O’Neill,” and the lion, “everyone else.”

As the senior managing partner of Sandler O’Neill, a New York-based multi-faceted investment banking company, Dunne is the ultimate up-and-runner who long ago fulfilled his up-and-comer destiny. In business, in personal life, in the game of golf, the guy who is known by friends as the “Dunne Man” is up at the crack of dawn and ready to go—24/7 and 365 if need be. And he’s known to smoke a fine cigar whenever he can.

The life of Jimmy Dunne is the stuff of dreams—and of a nightmare. At the heart of it is the 27-year marriage to wife Susan and their three children. At the forefront of it is his role as the leader of a very successful business. At the soul of it is his ion for the game of golf. The man is 62 years old but lives a life so expansive there doesn’t seem to be enough time to cram it all in, especially considering he’s an avid and accomplished golfer who plays to a single-digit handicap. He has a resumé of club hips that borders on the astonishing—Augusta National, Shinnecock, Seminole, Cypress Point and Pine Valley, to name a few—and a roster of A-list friends across all strata of society.

“He’s a guy who is really comfortable in his own skin,” says Tom Brady, the New England Patriots quarterback, one of Dunne’s many friends. “He says what he thinks, means what he says and is very endearing. He can be tough, but he’s incredibly warm. I think for Jimmy, the harder something is to accomplish the harder he works at it. It’s the hallmark of a great leader to hunker down and work harder than anyone else.”

Golf feeds Dunne’s competitive spirit, nourishes his social nature and nurtures his vast connections in the financial world. “Golf has been an important part of my life for as long as I can ,” says Dunne in his slightly raspy New Yorker baritone, which commands attention while not demanding it. He looks you in the eye, delivers his message clearly and crisply. “It started with my father; he had a great appreciation for the game,” he says. “He thought it enhanced all the great characteristics—you’re outside, you are moving around, you are at pretty places, you are enjoying the day and you are around really nice, successful people. He thought it was an absolute, fantastic game and he instilled that into me.”

And the game of golf saved Jimmy Dunne’s life.

Seventeen years ago Dunne was playing so much golf—and so well—that he was becoming increasingly interested in playing competitively. On the morning of September 11, 2001 he was at the Bedford Golf and Tennis Club north of New York City, trying to qualify for the U.S. Mid-Amateur Championship. His mentor Herman Sandler had told him not to call in that day, just concentrate on playing his best, and after a frost delay he was off to a strong start. After four holes on that crisp, perfectly clear day, he was one under par, when he was approached by a tournament official who delivered the horrifying news of what was unfolding in downtown New York, what was happening at his company headquarters back in the Twin Towers of the World Trade Center.

Dunne’s original plan was to attempt to qualify a day earlier, on a different golf course. But Chris Quackenbush convinced him to change his plans. Quackenbush was Sandler O’Neill’s head of investment banking, and he was Dunne’s best friend. They had known one another since high school. “He picked up the application. He said ‘Go to Bedford on the 11th—you’ll get it under par,’ ” says Dunne. “I picked up the application, I handed it to Debbie.” Debra Paris was Dunne’s assistant. “Debbie died,” says Dunne, his voice loud, a hint of pain in his eyes. “Chris died.”

Sandler O’Neill had 171 employees who worked on the 104th floor of Tower 2, the South Tower of the World Trade Center. Eighty three of them came to the office on 9/11. Sixty six of them perished, including Quackenbush and Sandler.

Had it not been for his change of plans, Dunne would have been at the World Trade Center that day. But that round of golf saved his life. Kept him here to live on, to keep Sandler O’Neill functioning.

Dunne raised the firm from the ashes of that devastating day. He led a rebuild of a company that had lost nearly every trace of its financial records, many of its partners and an enormous amount of the people who formed the firm’s intellectual capital, who did its day-to-day business. The company had lost all its computers, its phone numbers. Every aspect of the business had to be painstakingly restored.

Dunne made sure that salaries and bonuses were paid, health insurance was taken care of, that there was a fund for college scholarships for the firm’s children. He spoke at no fewer than 20 of the funerals. Dunne’s hard-charging nature, his absolute determination and his devotion to those he cared about meant that he would fight the ultimate fight.

“Whether it was the guys I caddied for, the teachers that I had, coaches that I had, the parents that I had, the sisters that I had, all those people who took time and effort and invested in me, this was the moment their kindness and their confidence in me needed to be paid back,” says Dunne. “Regardless what would happen, if I had to give it my absolute all and either successfully do the right things or literally die trying, and I was very willing to pay that price.”

Sandler O’Neill managing director Richard Olstein, who hired Dunne for his first job in finance in 1978 at the firm L.F. Rothschild, recalls the Herculean efforts that Dunne put in the months and years following 9/11. “In my view, he is the only person I know who could have taken this firm from where it was after 9/11 to where it is now,” says Olstein. “He’s got very strong character. He’s concerned not only about execution but the manner of execution and he wants things done right. He’s demanding of the people who work for him, but no more than he is demanding of himself. He’s a terrific leader.”

After the attack, golf was on hold for Dunne—he spent nearly all of his time on resurrecting the firm. It took a couple of years before he could get himself to feel good about playing again, about being back with his vast array of friends that he had made through the game.

One of those friends is Seth Waugh, former CEO of Deutsche Bank Americas and the new CEO of the PGA of America. “He is an enigma of sorts, both the simplest and the most complicated,” says Waugh of Dunne. “He’s got very strong opinions and yet he’s also the most loyal guy on earth and at the end of a day a teddy bear… He’s always rooting for the guy that’s down and yet he walks with the kings.”

Lou Nanni, vice president of university relations at Dunne’s beloved alma mater Notre Dame, says Dunne “has this rare ability to develop rich and meaningful relationships with those struggling on the margins as well as those who are very successful and are at the highest levels of society. He’s a study in contrasts. His combination where he is hyper competitive, but he is also genuinely comionate. I see that as a rare combo. He’s knows brokenness. The brokenness in his own life has led to incredible comion.”

James J. Dunne III grew up in the Long Island village of Babylon, 40-odd miles east of Manhattan. He was the only son in a house filled with four sisters, raised by his mother Ann and his father James Joseph Dunne, an executive with Arrow Shirt Company. From the get go he was a hard charger who knew the value of money and the independence it would bring, and was as demanding of himself as he would become of others. “My parents instilled an attitude if you wanted to get something done, you had to go out and get it,” says Dunne. “Nothing would be given to you. My mother developed an underdog mentality in me. Sort of the opposite of today where you are the greatest star in the sky. Her attitude was ‘Jimmy, all these guys are tough, people are smarter, people are faster, you gotta go. You got to get up and go get it.’ It worked for me. It doesn’t work for everyone.”

It was his father who introduced him to golf, first at muni courses on Long Island, then by ing the Southward Ho Country Club in Bay Shore. “I can still [my father] saying ‘Jimmy, they don’t have tee times there,’ that you can come, hit a few balls and play. We were used to waiting three or four hours to play nine holes.”

Driven to make money to establish his own independence, Dunne got a job caddying at the club at the age of 11, telling everybody he was 14. His father had often told him that part of being successful in life was being able to anticipate the consequences of his actions, or those of others. With a 25-pound bag on his shoulder, he learned to anticipate the needs of his player. Maybe even more important was learning to coexist in the caddie yard with a hardscrabble group from a different social strata. “I got a good education about golf and life in that caddie yard. I didn’t go in there with any feeling of entitlement,” says Dunne. “Caddying was a huge piece of the foundation of my life because I knew what it felt like when the guy put the $7 in my hand rather than $5.”

The man who would eventually become one of the smart guys of the Wall Street world was learning his trade at Southward Ho, even if he didn’t know it. He learned to play golf for money on Mondays, caddie day, and he played cards with the other caddies on his downtime. “They played gin rummy, which I had to get good at quickly,” says Dunne. “They played for money and nobody liked to lose any money, and there was value in someone who was good and sharp and a good gambler. That was status.”

Dunne learned an early lesson one day when his partner, a caddie named Leroy Brown, called him an idiot for breaking his club in a fit of anger during a money match, letting him know that he wouldn’t be out just the money for the match, but also the cash for replacing the club. “He spoke to me as an equal. I wasn’t a spoiled member’s son who just did something stupid. I was his partner who lost my temper, had a violent reaction and he was unhappy and disappointed in me as a partner, not as a young man or a member’s son. I feeling the responsibility. That made a big impression on me.” (To this day, Dunne has a soft spot for caddies, and he frequently brings caddies to Augusta National, where he has been a member since 2006.)

One day, at the driving range at Southward Ho, Dunne met Quackenbush, who would become not only a golfing partner but his soul mate and coworker. Long before they worked in high finance, the two toiled together in a far simpler way. He and Quackenbush wanted to raise money to pay their own college tuition, so they started a house painting business. Their business card read “Tuition Paying Painters.” With the ultimate stroke of good fortune, one of the houses they painted belonged to a member of the iconic Shinnecock Hills Golf Club, who arranged for them to play. Playing the course with a jaw that was often agape, Dunne knew he wanted to be a member, even if he didn’t know exactly how he would do it.

Dunne went to Notre Dame, and graduated in 1978 with a bachelor of arts degree with a major in economics. He grew to love everything about the school, and has made frequent donations to his alma mater. In 2016, he and his wife Susan donated $20 million to build a residence hall that is named after him.

When Dunne didn’t get into Georgetown Law School, the series of connections he had made through golf brought him to the financial world. He met Sandler in 1978, and in 1988, Dunne ed Sandler and other executives from Bear Stearns to found Sandler O’Neill. Soon, Quackenbush ed, coming from Merrill Lynch. All was roses, a blossoming firm at the top of Tower 2, until the devastation of 9/11.

The events of 9/11 are never far from his thoughts, though he doesn’t like to dwell on them. His mission to save Sandler O’Neill was undeniably a success, as the company is bigger than it was before, with some 320 financial professionals. The private firm doesn’t disclose revenues. Dunne says that what happened didn’t change him, it just motivated him even more. “Sometimes something happens in somebody’s life and they say that changed them,” Dunne says. “9/11 didn’t change me a single bit. Not one iota did it change me. The intensity in which I felt things was different. So when I hugged my children good night I know that I held on longer and a little tighter.”

“The guy’s got a heart as big as the state of Texas,” says John Bannon, a lifelong friend in the financial business who is also a fellow golfer and occasional caddie for Dunne in the AT&T Pebble Beach National Pro-Am. “The kids of the fathers and mothers that we lost in 9/11, to see that their kids had nothing to worry about as far as school and insurance? You could say that he’s a guy that tries to do something for someone every day and not expect a thing in return. I’m pretty psyched to call him a friend.”

Dunne has made endless friends through golf and business. That’s where he met Brady, and so many other people who love the game like he does. He is president of the Seminole Golf Club in Juno Beach, Florida, where he plays with pros such as Phil Mickelson, Rory McIlroy, Justin Thomas, Nick Price and a host of other big names. “He’s one of a kind,” says Thomas. “What I respect about him is that he is so well-respected and worked very, very hard his whole career to get where he is.”

Dunne and Waugh used to have an annual outing, five men and their sons playing golf and learning about the vastness of life. One year, Waugh hosted the group for dinner in the Hamptons. He knew how much Dunne had put into resurrecting Sandler O’Neill, how he was virtually nonstop. On this night, he saw a different Dunne sitting on the beach.

“We sat there in the dark and he was smoking a cigar,” says Waugh. “He was as content as I’ve ever seen him.”

Dunne likes to smoke a fine cigar wherever he can. He’s especially fond of Cohiba Behikes—when he can find them. He smokes in his den, on the golf course and by the pool at his house near Seminole. “I find time late in the day, when everything is done,” he says, “to sit down for an hour or so with a cigar—I really enjoy it.” He began smoking cigars as a young trader, emulating the move of one of the firm’s veterans.

Cigars played a role in one of Dunne’s deals: the multibillion dollar acquisition of John Middleton Inc., the maker of Black & Mild machine-made cigars. John S. Middleton, the principal owner of the Philadelphia Phillies, had known Dunne personally for a few years, and approached him when he thought about selling. “I said to Jimmy, ‘I know this isn’t your space, but I trust you,’ ” says Middleton. 
“He has the highest set of ethics and morals that I’ve ever seen.”

Middleton thought his cigar company was worth X. “I said, ‘I think it’s worth X-plus,’ ” says Dunne. Altria Group Inc. bought Middleton for $2.9 billion in cash in 2007, with Sandler O’Neill serving as financial adviser. A memento of the deal sits high on one of Dunne’s office bookshelves.

When asked if a $2.9 billion deal is a big one, Dunne’s eyes light up. “I’m from the Anthony Quinn school,” he says with a small smile. “There are no small deals.”

Deals of that size deserve celebration at places like Shinnecock, a course that awed a young Dunne with its majesty and beauty so many years ago. Today, he’s not only a member, he’s been club champion three times. He also shot a 63 there in 2010, a round that included an ace on the par-3 11th hole. The ball lay in the hole with the large Q facing upward, the way Dunne has always marked his ball since the death of Quackenbush.

Dunne has given and gotten so much through golf, and sees it as a way to get to the heart of a person. “I had a friend who once said you don’t really know somebody until you’ve had dinner with them or played a round of golf with them,” he says. “I’m not sure about the dinner, but I’m positive about the round of golf.”

And last summer, all those rounds finally brought Dunne to the only place on the course that had long eluded him—playing as a competitor in a USGA event. On July 30, Dunne shot a 73 at Tavistock Country Club to earn a spot in the 64th U.S. Senior Amateur Championship. As soon as he made the roster, the congratulations came pouring in, including a celebratory tweet from Justin Thomas. “The first USGA event for the Dunne-Man!”

It wasn’t a great tournament for Dunne, but he crossed one big, longstanding item off his to-do list that day, one more accomplishment in a life filled with them. And he played the same way he has for more than 17 years, hitting a white ball decorated with that letter Q, his constant reminder.

Given his standing in the business world, his portfolio of golf clubs, his roster of friends, his history of doing good by all, the Dunne Man might just be the ultimate golf partner.