Gloucester – Richard D. Wilson, age 82, of Gloucester, MA passed away peacefully on July 20, 2023. Son of the late Robert and Alice (Dennett) Wilson, he was born in Gloucester on October 11, 1940. He was preceded in death by his wife of 58 years, Barbara (Fitz) Wilson.
Dick loved growing up in Gloucester, where as a child he spent a lot of time on the sports fields and running the table at Nick’s pool hall. He was a crafty lefty who threw the very first pitch for the new Gloucester Little League program in 1953. A graduate of Gloucester High School, class of 1958, he was a standout baseball and basketball player.
Dick attended Bates College where he met the love of his life. He and Barbara married in 1960 and transferred to UMass Amherst where Dick was a star pitcher on the baseball team, while they juggled classes and the responsibilities that came after welcoming their first son, Rick. After college, Dick had a brief stint in the Majors before moving to Jonquiere, Quebec, Canada to continue playing professional baseball. It was here that their second son, Glenn, was born.
As their family expanded, Dick and Barbara settled back in Gloucester. Dick began his career in the insurance business and became active in the local Gloucester community. With their five sons in the Gloucester public school system, Dick served on the school committee from 1966-1980 with a long period as chairman. He was a passionate supporter of youth sports, coaching Little League baseball for 15 years. He and Barbara would create an outdoor ice rink in their yard in the winter that served as the gathering spot for many kids in Magnolia.
Dick’s belief in the importance of insurance protection for families helped drive his success as a salesman, mentor, and senior executive with New England Life and later as the senior partner at Baystate Financial Services in Boston. He went on to consult for many years with Penn Mutual Life Insurance Company.
Dick relished Boston sports as a season ticket holder for both the Boston Celtics and the New England Patriots. He also supported the Boston homeless community by taking a leadership role in the public/private partnership with the Pine Street Inn.
Dick believed in the importance of mentoring and attributed much of his personal success to the invaluable lessons he learned from his own mentors. Mentorship was the bedrock for giving people, regardless of circumstances, chances and making a difference in their lives, with a number of people considering him a second father.
He and Barbara spent winters in their retirement years in Kona, Hawaii, while remaining active in Gloucester. Dick spent his time fundraising for various charities, including Wellspring, The Open Door, Gloucester Fisherman Athletic Association, Gloucester Education Foundation, Gloucester Little League, The Newell Stadium Renewal, The Magnolia Pier, and The Young Legends Ball Hockey Rink in Stage Fort Park. He was a facilitator with a unique sense of humor and persistence who could connect a project or something near to his heart with others who were willing to support the cause. He was able to get things done without taking himself (or anyone else) too seriously.
Among his many honors, he was the recipient of the Distinguished Service Award of the Yankee Clipper Council (Boy Scouts of America) and the Linzee Coolidge philanthropic award. The Little League field at O’Maley Innovation Middle School is named Wilson Field after him. In 2020, The Open Door food pantry established the Dick Wilson Upsizer Award.
Dick is survived by his five sons and spouses: Rick and Roberta (Lexington, MA), Glenn (Manchester, MA), Steve (Fairfax, VA), Gary and Noell (Oxford, MS), Chris and Lauren (Greenwich, CT); grandchildren: Drew, Cam, Dylan, Hattie, Faith, Samuel, Elliott, Winnie, Hugh, Sara, Abby, and Hannah: also, nephew Bobby (Clearwater, FL), nieces Donna Kecyk (Gloucester, MA) and Sandra Misuraca (Gloucester, MA).
He was preceded in death by brother, Robert.
Visitation will be held on Thursday, August 3rd from 4 to 7 p.m. at the foyer of the O’Maley Innovation Middle School in Gloucester. Funeral service and celebration of life will be at the Unitarian Universalist Church, 10 Church Street, Gloucester, on Friday, August 4th at 1:00 p.m. Relatives and friends are cordially invited to attend, and casual attire is encouraged.
A private burial ceremony will be held at Oak Grove Cemetery where his ashes will be interred.
In lieu of flowers, contributions can be made in his name to the Gloucester Education Foundation, P.O. Box 1104, Gloucester, MA 01931.
Arrangements by the Greely Funeral Home, 212 Washington Street, Gloucester.
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