Jack Norman Sheppard, Jr.

Jack Norman Sheppard, Jr., 90, passed away peacefully on June 14, 2015.  Jack grew up in Brookline and spent most of his working and family life in Natick. He then resided in Dover and then Wayland with over 20 years wintering on Sanibel Island, FL.

Jack led a life filled with fun, business, family, friendships, practical jokes, boats, tennis, laughter, and community service. He featured a natural and down-to-earth charisma and garrulousness that endeared him to many devoted friends and admirers.

Jack’s charm and gregarious nature carried him through Brookline High School, a Naval career beginning as a teenager as an enlisted “tin can sailor” on the USS Ericsson during World War II, business acumen as the star salesman and national sales manager with his dad, Jack N. Sheppard, at New England Robes Corp.in Natick, and later for other apparel lines..

His life was enriched by a love of tennis and a multitude of friends, coveted winters on Sanibel Island highlighted by boating, fishing, and running on the beach; and a longstanding stint as the legendary fundraiser for the Newton YMCA.

Jack deployed his wry humor, generosity, and devotion to family and friends across a wide span of residents of Natick, Dover, and Wayland, MA, and during coveted winters on Sanibel, Island. Jack founded a weekly tennis contingent at the Longfellow Racquet Club in Natick in the 1970’s which still continues to be known as the “Jack Sheppard Group.”

Jack was always exactly who he was – nothing more or less. He was equally comfortable sweeping the floors of the Queenland Robes factory and, as early as the 1950s driving his Lincoln Continental convertible complete with a car phone. His customers loved him – the birthday cakes and cards, summer days besides the Sheppard family pool, and other acts of kindness.

In addition, Jack came to count among his dear friends, leaders of Massachusetts business, medicine and politics, as well as a broad assortment of neighbors, serious tennis players and weekend hackers alike, and people of all ages, backgrounds and stations, all of whom Jack treated with equal esteem and with characteristic warmth.

To his family, led by his devoted wife of 55 years, Annabelle, and his children Audrey, Bud, Cynthia and Melinda, he was astoundingly generous and impeccably dedicated. His high character was well demonstrated when he married Annabelle, a widow with three young children and immediately adopted them, and provided a lifetime of wonderful fatherhood, university educations, cars, advice, guidance, and love. He and Annabelle reveled in their own biological child, Melinda, who grew up to embody many of Jack’s most inimitable and winning personality characteristics.

Later, Jack embraced his role as “Buppa” and/or “Grandpa Jack” to grandchildren Natasha Vallett (daughter of Melinda and Chris Vallett) of Nantucket, MA; Julia and Daniel Lavenson (children of Cynthia and Peter Lavenson) of Wayland, MA; and David, Flora and Daniel Sheppard (children of Kathleen and Bud Sheppard) of Spokane, WA.

Other close relatives include his brother Michael of Natick; and his daughter Audrey now of Washington, DC; and his deceased sister Dorothy Marson.

Jack was fortunate in his final years to find a team of remarkable caregivers at the VA Hospital in Bedford, MA. They were able to cater to Jack’s occasional sparks of his former wit and humor. The family requests that any contributions go to Jack’s memory go to the Bedford VA Hospital, Bedford, MA.

Services at  Wilson Chapel, 234 Herrick Rd, Newton Centre ( on the grounds of Andover-Newton Theological School), on Wednesday, June 17, 2015 at 11:00 am. Following interment at Beit Olam East Cemetery, 42 Concord Rd., Wayland, memorial observance will be held in the Clubhouse at The Hills (Mainstone), 133 Hillside Dr., Wayland. Memorial observance will continue at Jack’s residence on Wednesday 7-9 pm, Thursday 2-4, 7-9 pm, and Friday 2-4 pm. Remembrances may be made to Rogers Memorial Veterans Hospital, 200 Springs Rd., Bedford, MA 01730 or Beth Israel Deaconess Medical Center, Office of Development, 330 Brookline Ave., Boston, MA 02215 (Please memo check in memory of Jack N. Sheppard, Jr.)