Some people have the innate ability to impact the lives of others. Richard “Dick” Connolly Jr. is one of those people. In fact, Connolly, who received the 2025 Francis Ouimet Award for Lifelong Contributions to Golf from the Francis Ouimet Scholarship Fund on Monday, may have been impacting lives before he even knew it.
In the mid-1960s, Connolly was working on the maintenance staff at Woburn Country Club, a nine-hole course located just outside of Boston. One day he walked into the pro shop and found his friend Don Hearn working the desk. In that moment, according to Hearn, Connolly suggested Hearn join the superintendent team. Hearn took the suggestion, setting the stage for a 50-year career in golf mostly as a superintendent, culminating with his recent retirement as the executive director of the Golf Course Superintendents Association of New England.
The story Hearn shared only scratches the surface of who Connolly is and what he stands for. Connolly was first introduced to the game of golf when, as an 8-year-old, he began caddying at Woburn Country Club. To this day Connolly, a 2023 inductee into the Caddie Hall of Fame, calls that job the most important job he has ever had.
“[Being a caddie] was the single most valuable experience I’ve had in my life,” Connolly said at the time of his induction. “The fine people I caddied for taught me so many lessons in life, and, to this day, I believe caddying is the best way for a young person to learn.”
The son of Richard and Ruth, Connolly and his brother Robert eventually joined the Woburn Country Club maintenance team. It was during his teen years while working for the maintenance crew that Connolly found out about the Francis Ouimet Scholarship. The chain reaction that discovery set off is astounding.
In need of financial assistance to help offset the cost of college, Connolly applied for and received the Francis Ouimet Scholarship.
“Receiving the Francis Ouimet Scholarship was so important for me,” said Connolly, who attended the College of Holy Cross in Worcester, Massachusetts, and played on the golf team. “My parents didn’t have a dime. The scholarship was critical to me being able to pay for school.”
After graduation in 1961, Connolly initially worked in the automobile industry as a zone manager for the Ford Motor Company. In his role with Ford, Connolly spent countless hours on the road calling on dealers.
Nevertheless, Connolly’s time with Ford was just the opening act to his professional story. During his travels for Ford, Connolly often met with college friends and many of them told Connolly he should consider working in the investment business. “I didn’t know a thing about stocks or bonds but some of my friends had fathers who worked on Wall Street and after I went to talk to them I was completely intrigued by the business,” Connolly remembered.
Regardless of how successful Connolly was professionally he never forgot the life-changing opportunity that the Francis Ouimet Scholarship presented him.
So Connolly took a leap of faith, leaving Ford in 1968 to join Merrill Lynch and enter the company’s training program. Once he made the switch Connolly never looked back, spending more than a half century in the financial industry.
Eventually, Connolly, who retired last year, moved to Morgan Stanley and launched The Connolly Group. However, regardless of how successful Connolly was professionally he never forgot the life-changing opportunity that the Francis Ouimet Scholarship presented him.
“I just felt I owed it back,” explained the 84-year-old Connolly when talking about his more than 40 years of involvement with the Francis Ouimet Scholarship Fund, which helps deserving young men and women who have worked at golf courses in Massachusetts obtain a college education. “The motto with the Ouimet Fund is, ‘What golf has given to you give something back to golf,’ and I believe that to the nth degree.”
Over the years Connolly has served as president, director, trustee, and is still an active member of the executive committee. Connolly, married 43 years to his wife, Ann Marie, has committed countless hours to the Francis Ouimet Scholarship Fund including putting the fund on the national stage when he invited and then welcomed longtime friend and client Arnold Palmer to the fund’s 1997 annual banquet. That year Palmer not only helped turn the banquet into the largest golf dinner in the country but he became the first golf dignitary to accept the Francis Ouimet Award.
“Before 1997 we had a few hundred people at the banquet,” said Colin McGuire, the Francis Ouimet Scholarship Fund’s executive director. “It was geared more towards a celebration than a fundraiser but when Dick brought in Palmer and then in every subsequent year since then [collectively], the banquet itself has raised an additional $15 million towards the scholarship effort. So, Dick is responsible at a minimum just with this one program alone for raising $15 million for the Ouimet Fund.”
Still, when talking about his impact on the lives of hundreds of young adults Connolly remains modest.
“Earning this award is the greatest thrill of my life,” Connolly said when asked what being named the 2025 Francis Ouimet Award recipient means. “We’ve done so much for kids that need financial aid. We have given out close to $60 million since the Ouimet Fund was founded in 1949. We have honored Arnold Palmer, Jack Nicklaus, Gary Player, Tom Watson, Ben Crenshaw, and George H.W. Bush among many others. It is mind boggling the people we have honored. For me to even be mentioned in the same vein as those people it is hard to believe.”