Official Caddying Story: Dick Connolly
Dick Connolly is an accomplished Private Wealth Advisor who has managed investment portfolios for several decades. He has built his business by providing sound investment advice to high net worth families, foundations, nonprofit organizations and other financial institutions. Dick’s reputation as an investment manager in Boston has been earned through many years of hard work and dedication to his clients. He is firmly committed to fostering long-term relationships and strives to deliver exceptional client service. Dick began working as a financial advisor in 1969 at Paine Weber, where he spent the majority of his career.
Dick Connolly’s involvement in educational and philanthropic institutions is as varied as it is vast. Some of his charity work includes the Boston Symphony Orchestra, The Alzheimer’s Association, New England Province of Jesuits, Francis Ouimet Scholarship Fund, Fenn School, College of the Holy Cross and Children’s Medical Research Foundation benefiting Our Lady’s Hospital in Dublin, Ireland. Additionally, he is a generous supporter of Boston’s Camp Harborview, Inner City Catholic School Initiative, Catholic Charities, and Mass Affordable Housing Association (MAHA). Dick is the Chairman of Children’s Medical Research Foundation (CMRF) annual golf tournament which he has successfully chaired for the last 30 consecutive years. In recognition of his philanthropic efforts, the CMRF recently dedicated a wing of the hospital, The Richard F Connolly Microscopy Centre. Dick was honored to have this part of the hospital in his name knowing what an integral role research plays in finding cures for sick children. Another charity close to Dick’s heart is the Francis Ouimet Scholarship Fund where he is both a scholarship alumnus, Director, Trustee and former President who has proudly served the Ouimet Fund for over 35 years. He has been a driving force in starting and sponsoring the Francis Ouimet Award for Lifelong Contributions to Golf Annual Banquet, and he created an endowed Ouimet Scholarship in his family’s name, among countless other things.
Dick is a graduate of The College of Holy Cross and earned his MBA from Babson College. He is a member of Morgan Stanley’s Chairman’s Club. Dick has been married to his wife, Ann Marie, for 39 years. They have three sons and live in Concord, Massachusetts.
At which golf course did you first caddie, and how old were you when you started?
I started caddying when I was 8 years old, believe it or not. It was at Woburn Country Club, a 9-hole golf course in Woburn, Massachusetts.
Why were you compelled to become a caddie?
My mother was from a family of 10; she was the only girl and the second oldest. Of her 9 brothers, they all caddied, but 7 of them were legitimately a 5-handicap or better. They all could play. One was among the top amateurs in New England; his name was Ernie Doherty. They grew up dirt poor, so they caddied to bring money home to the family. It was because of them that I later started caddying. I say to this day, I’ve never had a better experience than my days as a caddie. The people I met became an extension of my own family.
Take us through your first day on the job, who was your first loop?
I was young, and I was small. So, I could only carry one bag at first. At 10 or 12, I could handle two. To get to the course, I’d either walk or ride my bike, usually getting there really early in the morning. My first loop was Dr. Paul Driscoll. He was very nice to me and that first day he even carried the bag for me for two holes!
What was the biggest mistake that you made during your caddying career?
One time, I was tending the flag when my guy was attempting a 30 or 40 footer. As the ball approached, I couldn’t pull the flag out! I was a little kid; I wasn’t strong enough at the time. The ball hit the flag and bounced away. The member just laughed; he was really great about it.
The members were just so good to me. They were the ones who really taught me to caddie. My parents told me to be polite and speak when spoken to, but it was the members who taught me the job, in a very nice way. There was a lot of learning on the job, where to stand, getting pins, and stuff like that. My experience was nothing but the best.
To this day, when I see someone not being nice to caddie, that really aggravates me. In most cases, the caddie is doing the best he can. The vast majority of the members who I caddied for were terrific to a young kid who was learning. I’d like to think that holds true today.
What did you most enjoy about caddying?
I loved being outside and around the game. I enjoyed the exercise and overhearing the conversations of the players. Late in the afternoon, some members would even let me hit shots. I never got golf lessons. Instead, I’d just mimic the good players at Woburn, and there were a lot of them. Copying the good players helped me become one in my own right.
Even today, when I see someone playing, I can always tell if they caddied. Just stuff like where they tee the ball up and how they conduct themselves.
Tell us about some of the people for whom you caddied, did any of them contribute to your career in a meaningful way?
There were many, but here are a few specific ones:
Jim Powers, he owned a construction company in Arlington, Mass. I’ll never forget when I was caddying for him, maybe around 12 years old, and he said, “Be good to your parents when they’re alive. After they pass on, it doesn't do any good to go to the cemetery.” It was good advice, and I had a great relationship with my parents.
Dick Foley was another. He asked me one day, “What do you want to be in life?” Of course, I wanted to be a pro golfer, to go on tour. He told me, “Whatever you want to be, to be good at it, you’ll have to spend a lot of lonely hours on it.” He was right about that. To be good at anything, you have to put in the work.
Paul Sheeran was another. He had actually played high school football with my father. My dad was an outstanding athlete but never went to college. Paul became a dentist, so he invited me down to his office. I went down one day, and he takes me out to get a sandwich. He said, “You’re a young guy. You can go any direction you want to go. Being a dentist has been great to me, but dentistry is not for everyone. Whatever you decide, make sure it’s something you really want to do.” It was the summer of my sophomore year in college. I ended up studying History at Holy Cross because it was a good general major. You could go into law, business, or engineering. He gave me really great advice that day, and he happened to be one of the better players, too.
What was the biggest lesson that you learned from caddying that helped you succeed as you progressed in life?
It taught me a lot about competition. There were tremendous competitors out there, and if there was a 5 or 6 foot putt that meant something, you knew the guys who were going to make it and the ones who wouldn’t.
I learned about the honesty associated with the game. If the ball moves, you call it on yourself. I saw that as a young boy: the right way to do things. Golf is maybe the only sport where you run in and help the opponent find a golf ball when he hits it into trouble. In a lot of other sports, it’s about cheating or grabbing a jersey when the ref isn't looking.
What can you tell us about Arnold Palmer, since you and the King were close friends and he was your client for many years?
Arnold Palmer was better than his press. Very few people are better than what you read about them in the papers, and even though the press loved Arnold, he was an even better person than most people will ever realize.
I was working for Paine Webber at the start of my career. The gentleman who ran the investment business was Don Marron, and he loved tennis. So, we had Jimmy Connors as our spokesperson. Being a golfer, I kept asking why don’t we have someone like Arnold Palmer? It seemed like we were missing a great opportunity to win business among golf fans, so I just kept bringing that up.
They finally arrange for Arnold to fly to New York to meet with Marron. When they go to lunch, Arnold receives a standing ovation from everyone in the restaurant, so they saw what a huge star he was. Marron told me afterwards, “We’re gonna hire your boy.” Now, Arnold was the only sports figure I ever idolized, but I'd never met him. So, I asked if he had an account with us. It turns out he didn’t, so I was sent down to open one up for him.
I go down to his office in Florida at Bay Hill. I was petrified. His office was right above the pro shop. I’m still a young kid. To my surprise, he came out and got me, not his secretary. Arnold came out himself! We talked for 2 hours. Arnold was a caddie growing up. We talked about our upbringings and the significant influence of our parents on us. We found a shared love of our great country and for loyal friends.
At the end of our meeting, he touched me on the shoulder and said, “You do your job, and I'll do mine.” It was an incredible relationship. He even came and spoke at my oldest boy’s high school graduation years later.
That all came from golf. And as I said earlier, Arnold had caddied himself, and it was part of our bond.
If you could nominate one former caddie who went on to enjoy success, whose Official Caddying Story would you like to hear?
One of my close friends, Peter Lynch is one of America’s most successful investors. He is a fellow Ouimet Scholar and often speaks about how caddying in Massachusetts shaped his life and career.
*This interview has been edited and condensed.
