William James Flynn

April 22, 1931 ~ February 22, 2022 (age 90)
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ROCKPORT - William James Flynn of Marco Island, FL and Rockport, MA departed on February 22nd, 2022, at 2:22 pm with his wife Dorothy, and daughter Ryann by his bedside.

He leaves Dorothy, his loving wife of 62 years; his children, Shannon, Ryann and FitzJohn; son-in-law, Stanley Poole, his son, John Poole and wife, Rachel. He is survived by his brothers, Roddy and Larry; sister, Marilyn Newhook (DOD 7/17/22); in-laws, Robert Scigliano, Linda Flynn; cousins, Mary Jo (Larry) King, Mary Alice (Bob) Wesley, Jack (Karen) Ross, many Sullivan and Bulger cousins, many nieces and nephews, and dearest people Erika McKee, Michael Richardson, and John LeMon. William is predeceased by his parents, Frances and Harry Flynn; brothers, Jack, Charles, Harry, Frank, Gus; sisters, Geri Scigliano, Joan Tsuimis; in-laws Tom Newhook, Stewart and Charles Fisher, Helen, Mildred, Rita, Marna, Pat, and Phyllis Flynn, Anna (Fisher) DelBuono and Ginny Fisher.

Bill was born April 22, 1931, in Revere, MA. Obviously, someone needs to be playing the number 22 in the lottery! As one of eleven children he contributed to the family's finances as a newsboy, Filenes delivery boy, Revere Beach attractions ticket seller and announcer. He worked as a porter and lead-out Greyhound handler at Wonderland Park. In his youth, he MC’d, danced and sang for neighborhood organizations, St Teresa’s church and local city political events. An aspiring athlete, he played with the New England Hobos and tried out for the Boston Braves.

Bill volunteered during the Korean War, serving 4 years in the US Navy. Declining the honor of OCS, he agreed to an intense background investigation by the Office of Naval Intelligence and FBI to obtain a high security clearance. As team member planning the defense of the First Naval District, Bill mapped, communicated, and implemented senior directives, relaying vital information to worldwide Naval stations from an isolated Marine patrolled office. On board the U.S.S. Lake Champlain serving in the Mediterranean, he pumped information via Radio Free Europe to Iron Curtain countries and relayed security directives to naval bases.

Receiving an honorable discharge, he enrolled in Vesper George School of Art, and became one of their Fine Arts Instructors upon graduation in 1956. Associated with the Boston School of Painting, Bill's training was passed from Jerome, Inge, Degas, Cassatt, William Paxton, Ives Gammell, and then to Bill's mentor, Robert Douglas Hunter. Hunter encouraged Bill to establish himself as part of the Fenway Studios, but Bill fell in love and chose to raise his family in Rockport Massachusetts a picturesque seaside town with a rich artist and family community. At this same time although he was awarded a scholarship to The Hawthorne School of Art in Provincetown, he instead chose to study with Rutledge Bate in Rockport, Massachusetts where he had decided to settle. In 1960, he and Dorothy purchased a home with barn, which became the first William James Flynn Studio and Gallery. In further studies, he completed the Juris Doctor degree at New England School of Law in 1964.

Expanding his gallery to 57 Main Street in Rockport, he focused on selling his paintings during the summer and practicing his art the remaining part of the year. Many of his customers became lifelong friends and patrons. Bill was nominated to the National Academy and supported by Academicians Joseph Floch, Louis Boza, Arnold Knauth, Bill Meyerwitz, Theresa Bernstein, Joe Solman, Israel and Raphael Soyer, Leon Krol, and Harry Ballinger. Bill was not accepted, and while encouraged to apply again, he chose to focus on his family and painting. A close friend of Aldro Hibbard, Bill and Dorothy joined the Hibbards at many events and Artist Balls. Bill and Hib shared their passions for both art and sport especially baseball and boxing. Accepted by Lloyd Goodrich, Director of the Whitney Museum, Bill’s work was included in the Rhode Island Art Festival. Judged by 5 National Academicians he was accepted to the Boston Festival of Arts. His local and national awards include many from Allied Artists (Gold Medal), National Academy, New England Watercolor Society, Rockport Art Association and North Shore Art Association. He also won the Elizabeth Greenshield Memorial Foundation Grant for young artists choosing to study in Italy with Pietro Antigone. Unfortunately, the death of Antigone prevented this study. Bill was able to redirect the grant which allowed him to resign from teaching to concentrate solely on painting.

Disturbed by civil unrest during the 1960’s and ‘70s Bill composed, Floundering Democracy, a painted political satire on George Wallace's presidential candidacy. Bill agreed to sell the painting for a $1,000.00 donation to Opportunities Industrialization Center of America, Inc to help train disadvantaged persons.

Bill’s paintings are in the collections of the Maryknoll Museum, Washington; Dixie College, Utah; Greenshields Memorial Foundation, Montreal, Canada; and Telfair Academy, Savannah, Georgia. His painting, Security, was awarded the Henry Ward Ranger purchase prize by the National Academy. The painting is kept at Telfair and now as of his death may be claimed by the Smithsonian.

Listed in Who Who's in America, Bill had memberships in Young Democrats, Elks, St. Theresa Catholic Youth Organization, various baseball teams, Rotary, North Shore Art Association, New England Watercolor Society, Allied Artists, Salmagundi Club, Rockport Art Association, Marco Men’s Club, American Legion and AMVETS. Governor Edward King appointed Bill a member of the Massachusetts Council of Arts and Humanities. Under Governor Michael Dukakis, Bill served on the Massachusetts State College Board of Trustees. Bill was a successful businessman; real estate investor in MA, NH, FL; and a self-educated financier/trader.

Wholly involved in his children's interests and upbringing, he was an avid and often embarrassing supporter of their activities. Many a time, attendees would ask his children who was that bearded man – the loudest in the stadium! Adamant that they make their own life choices he fully supported their chosen course of study at the renowned high schools and colleges they chose to attend. He coached Rockport Little and Pony Leagues and travelled to most home and away athletic contests to cheer their teams. Bill instilled fan enthusiasm in his children following the Patriots, Bruins, Celtics, and Red Sox and boxing. The kids and Bill shared many an enjoyable competition in person and later over the phone on conference calls from Massachusetts to California.

Bill made every family Christmas memorable. His traditional 12-foot tree lit by blue and green lights was centered in the wide arched doors of his treasured carriage house. Decorated with antique and hand-blown glass ornaments, he covered the tree with single strands of hand hung lead tinsel. For years, Bill provided proof of Santa's visit with crumbs left on the cookie plate, wet boot prints on the carpets, sounds of reindeer hoofs, sleighbells, and footprints and sleigh tracks on the snowy deck to the wonderment of his children. Each year he hosted several holiday parties for family and friends.

Dorothy and Bill traveled extensively and often included their children. They planned yearly itineraries and when more time availed, they made two trips around the world visiting six continents. Bill’s father Harry always found a large coin to give to a youngster no matter how little in his own pocket. Remembering his dad’s generosity and wanting to emulate him, Bill always carried $10 bills while travelling, giving them out to young kids that they encountered staying in hostels.

On their 40th anniversary, Bill and Dorothy were surprised by their children with a Luau, which featured Hawaiian shirts and Leis flown from Hawaii and guests from many states. For their 50th anniversary their children flew them to Ireland for a family vacation. Their 60th Anniversary trip planned by the children was cancelled due to the pandemic but their daughter Ryann and loving son-in-law Stanley Poole, hosted a particularly special home celebration. Balloons and pastry were sent from the California children.

Bill had the gift of "gab" - comfortable with young and old, rich, or poor- he enjoyed talking to all. Quick witted and analytical Bill was always on top of national and world events, loved to talk about politics and the world around him. He could make an enjoyable conversation with anyone. Bill is remembered by his family as a loving husband and father, a highly respected artist, a clever entrepreneur, a successful financier, but mostly for his ambitious standards and morality.

ARRANGEMENTS: A Memorial Celebration will be held Sept 11th, 2022, at the Old Sloop First Congregational Church, School St. in Rockport, MA at 1 P.M.. Following the memorial service all are invited to continue to celebrate William's life in the fellowship hall of the church. In lieu of flowers, remembrances can be made to St. Jude Children's Research Hospital, 501 St. Jude Place, TN 38105, or Shriners Hospitals for Children, Attn. Office of Development, 2900 Rocky Point Drive, Tampa, Florida, 33607, or Friends of Rockport Athletics, Rockport High School, Rockport, Ma 01966. Assisting the family with the arrangements is O’Donnell Cremations – Funerals – Celebrations, 84 Washington Sq. (at Salem Common) SALEM.

To send flowers to the family or plant a tree in memory of William James Flynn, please visit our floral store.


Memorial Service
September 11, 2022

1:00 PM to 2:00 PM
The Old Sloop - First Congregational Church
School Street
Rockport, MA 01966

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