Dick Connolly – Trustee, Francis Ouimet Scholarship Fund

There is no one who has been more supportive, more passionate, and more dedicated to the Francis Ouimet Scholarship Fund than Dick Connolly.

Dick started caddying as an eight-year-old at Woburn Country Club and earned a Ouimet Scholarship to attend Holy Cross, where he captained the golf team before beginning a remarkable professional career.

He spent nearly 60 years in the financial services industry, becoming one of the most successful and respected advisors in the country. Exactly a week after this year’s Ouimet Banquet in late March, Dick officially retired as Managing Partner of The Connolly Group at Morgan Stanley.

One of his clients was Arnold Palmer, who became a dear friend and a passionate supporter of the Ouimet Fund. Dick was instrumental in expanding the Annual Banquet in 1997, an event in which Palmer was the first recipient of the Ouimet Award for Lifelong Contributions to Golf.

Dick and his wife of 43 years, Ann Marie, are the largest benefactors in the history of The Fund, and the Connolly’s have made a lifetime commitment to countless other charitable causes locally, nationally and abroad.

Dick’s philanthropic efforts are perhaps only topped by his modesty and his storytelling, and we hope you enjoy our second conversation with Mr. Ouimet Fund.

Click here to listen to all episodes.

2025 Ouimet Golf Auction

The Ouimet Golf Auction is now live! One of the largest of its kind in the country, the auction features nearly 100 unique opportunities to play top courses coast to coast. Click the button below to register today and check out this year's offerings!