At 16, Richard Francis Connolly Jr. had a vision for life. A golf prodigy at Woburn Country Club where his game was moving toward scratch, he queued up on a Friday night to a fully stocked buffet table that would have satisfied the most famished adolescent: steaming, lean roast beef, honey ham, sausage and pork, and a selection of thinly sliced deli meats that would delight a king. His buddies, all playing the following day in a junior tournament, put on the feedbags. To everyone’s surprise, Connolly wistfully walked away from the table empty-handed.

“You hungry, son?” a tournament director inquired. “Yeah, but I don’t eat meat on Fridays,” Connolly said.

Fully impressed with Connolly’s faith and discipline, the man replied, “You keep thinking like that, son, and you’ll be just fine throughout life. Always do what you think is right!”

Dick Connolly—today one of the country’s most successful stockbrokers, overseeing a team at Morgan Stanley that manages close to $4 billion in assets, a man whom Barron’s calls one of the nation’s top financial advisers, ranking him in the 99.96 percentile among some 300,000 brokers in the country — never forgot those words of counsel. His gut instincts have endured through all the birdies, bogeys, and mulligans of life. He’s fully comfortable in his own skin, and at 72, that’s something to say.

The pride of working-class Woburn, where he made his mark in this closely knit community and on the links of Woburn CC, caddying at the nine-hole municipal golf course from an early age and working there part-time through grad school at Babson, Connolly has remained faithful to his roots. He is a patron saint of caddies and individuals in need, with more contributions, affiliations, and honors to his credit than most anyone in Boston. In an edifying profile last year of Connolly’s accomplishments, the Boston Business Journal dubbed him the “Blue-Collar Broker.”

Connolly is all about the tick, tick—not so much the pulse of the stock market, but the spray from sprinkler heads that maintains verdant greens and fairways. You must water your resources, Connolly advises, to keep them green. Golf is life to Connolly, and he plays golf and life with verve. At home, work, and on the course ,where his handicap is still in the single digits, he lives the words of his idol, Arnold Palmer, who once said, “I never quit trying. I never felt that I didn’t have a chance to win.”

Connolly has never quit trying, even when it came to pursuing Palmer as a client. For 35 years, he has handled Palmer’s investments adroitly; they are close friends, to the point that Palmer gave the commencement address at Connolly’s oldest son Richard’s high school graduation. There are other celebrity friends and clients in Connolly’s loop, like hockey legend Bobby Orr, but he is equally comfortable on Horn Pond, a primary source of the Mystic River in proletarian Woburn. Perhaps that’s what endears them to him.

In the last census, the per capita income of Woburn was $26,207. When his father, Richard Francis Sr., worked in Watertown at BF Goodrich as a supervisor in the footwear section, “he never saw the north side of $12,000 in salary, but never owed anyone a penny,” says Connolly, who was raised with the admonition, “It doesn’t matter whether you’re handsome, rich or smart, if people can’t trust you, if they don’t think you’re a good person, then all is wasted.” Connolly is speaking in his Morgan Stanley office on High Street on Boston’s Financial District.

That admonishment had roots in Mayo and Galway, where his grandparents were born. Work ethic in the Connolly household was as much a staple as Sunday Mass and then pot roast for dinner.

“My dad was strict in his own way, but easy going so long as you toed the line,” says Connolly in noting that his father also was a Woburn alderman for close to 20 years. “He could have been mayor, but my mother wasn’t going to have any part of that.”

The elder Connolly was a star athlete at Woburn High School, one of the best in the history of the town. He played football and baseball, but never went to college. Instead, he paid the bills.

Connolly’s mother Ruth May (Doherty), second oldest of ten children, nine of them boys, seven of whom played scratch golf or close to it, “was the prettiest woman in Woburn; she had the whole package,” he says. “She never went to college, she never had a driver’s license, she never flew in a plane, and yet she was the single most impressive individual that I’ve ever known with her work ethic, concern for people, the way she dealt with adversity and serious illness in life. She was an amazing woman. I’ve been blessed to be around a lot of big people in life, and she was the biggest. She was that great.”

She was tough, too, never putting up with flak from Connolly or his sibling. “If my mother ever heard me sass someone, oh, my God, she’d tattoo me quick!”

In all ways, Connolly is the fine work-in- progress of his parents and his caddying days, which continue to propel him on Wall Street. “You see the best and worst in people on the course,” says this student of the links whose parents encouraged the study of the yin-yang of human nature.

“When you have great parents, you can’t have a better start than that. They don’t make parents the way they used to. I was never afraid of my folks, but desperately didn’t want to disappoint them. That kept me in line. It would break my heart to disappoint them.”

Yesterday and today.

No worries, his folks smile broadly at the Lord’s side today, as their son continues his pursuit of excellence into his eighth decade. There are no signs of retreat from this man with a leprechaun’s smile.

A jock at heart, Connolly’s 130-pound frame as a youth dictated his sport; it also helped that his uncles had game in their genes. So he turned to golf, becoming captain of the Malden Catholic High School team, then captain again at Holy Cross where early on he had visions of becoming a dentist before deciding thaty he didn’t want to spend his life “looking into people’s mouths all day.” So he majored in history, then turned to finance, earning an MBA in business at Babson.

His educational pedigree is not that simple; it buttresses his parents’ core Catholic values. With great promise, Connolly was offered a golf scholarship to Wake Forest University, which at the time boasted one of the finest golf programs in the nation. But since the university was founded as a mainstream Protestant school, no dice. His parents, with little financial resource, wanted their son to have a Jesuit education, and insisted upon it. The heavens opened, and Connolly was awarded a scholarship from the Francis Ouimet Caddie Scholarship Fund. In time, he reciprocated many times over, becoming a driving force behind the fund; he is its leading benefactor. He establishing the Ouimet Fund’s annual banquet and welcomed Palmer as its first honoree. That event is now the largest annual golf banquet in America. Over the years, the Fund has honored the likes of President George H.W. Bush, Jack Nicholas, Tom Watson, Greg Norman, Curtis Strange, Ben Crenshaw, Nancy Lopez, and others, raising millions in scholarship dollars for young men and women.

From the very start, mentoring has been the foundation stone of Connolly’s legacy. When he was 11 years old, he caddied for a successful businessman named Jim Powers who treated him like a son and instructed him on the need for practice, whether on the golf course or the board room. “If you’re going to be successful at anything, if you want to be as good as you can be,” Powers told him, “you’re going to have to spend a lot of lonely hours practicing. Practice. Practice. Practice.”

Connolly is still practicing, and quick to give praise to those on his team, an investment group at Morgan Stanley that includes talented brokers and staff, some of whom have been with him for as long as 27 years.

He points to his loving family as the prime motivation for success, particularly to his partner Ann Marie (Reilly) from Providence, who also attended Holy Cross. The couple is still joined at the hip to the college at Worcester, and Connolly often jokes about nemesis Boston College, “Are they accredited yet?” Connolly’s three sons also give him needed ballast: Richard, who teaches English and coaches soccer, hockey, and baseball at St. Sebastian School in Needham; Ryan, who works with his father after coming off five years on the New York Morgan Stanley trading desk; and Kevin, a regional marketing associate at Putnam Investments.

After graduating from Babson, Connolly began his business career at Ford Motor Company in its executive training program, then joined Merrill Lynch in 1968 where he was recognized as Merrill’s most successful “rookie” broker. But this was no rookie. In the early 70s, he was hired by Blythe, Eastman to run its Fixed Income Desk where he successfully managed accounts for local institutions. After PaineWebber acquired Blythe, then UBS, Connolly enjoyed a successful 34-year career at the expanded firm as a 30-year member of the elite Chairman’s Club and UBS’s top producing broker for more than 20 years. Maneuvering the often-serpentine pathways of finance with aplomb, Connolly joined Morgan Stanley in 2007, reaching Chairman’s Club status in only 10 months, something of a Wall Street record.

Along the way, Connolly has served on numerous cultural, non-profit, and charitable boards, including the Ouimet Fund, Boston Symphony Orchestra, Society of Jesus, Worcester Polytechnical Institute, and the Children’s Medical Research Foundation in Ireland where a wing at Dublin’s Our Lady’s Hospital was recently named in his honor. His awards are equally impressive: an honorary degree at St. Thomas Aquinas College in Sparkhill, New York; honors from Bridge Over Trouble Waters (BOTW), a high-risk youth counseling and education program; and the Laboure Medal from Boston’s Laboure College, awarded to a member of the business community who embodies the spirit of St. Catherine Laboure in generosity, humanity, and kindness. He also is among the leading annual contributors to more than 15 organizations and philanthropies. Among them: Catholic Charities, Inner City Catholic Schools, Boston Children’s Hospital, Wareham’s Tobey Hospital, Combined Jewish Philanthropies, Colby College, Davidson College, College of the Holy Cross, the Joey Fund benefiting Cystic Fibrosis Research, and The Pine Street Inn.
“I truly understand how lucky I am,” Connolly says. “I work very hard, but a lot of people work hard. I know it’s not all about me. The best lessons I ever got in life were from just basic people. I couldn’t have grown up at a better time.”

As to his financial acumen, he is quick to retort “I’m not saving lives.”

Dick, your parents and Jim Powers, your mentor, would call you out on that. You are saving lives. Keep practicing!

Greg O’Brien is president of Stony Brook Group, a publishing and political/communications strategy firm based on Cape Cod. A regular Boston Irish Reporter contributor, he is the author/editor of several books and writes for regional and national publications.