GLOUCESTER: John D. “Jack” Cunningham Jr., 93, of 730R Washington Street died in his sleep at his home on Lobster Cove in the early morning of December 5, 2009. He was predeceased by his wife of 60 years, Mary F. Cunningham.
Born in Gloucester on October 10, 1916, he was the son of John D. Cunningham and Ella Louise (Hodgkins) Cunningham. Jack was a graduate of the Gloucester Public Schools and MIT. He had a long career in the insurance business. After 25 years with John Hancock in Boston he started his own insurance agency in Gloucester, which was later merged with Babson-Elwell & Davis Insurance Agency. He was a veteran of World War II.
As a lifelong Gloucester resident, he participated in and supported many community organizations. Jack was instrumental in the replacement of the dilapidated Lobster Cove Bridge with the current wooden foot bridge.
He was a lifelong trustee of the Cape Ann Savings Bank and a former commodore of the Annisquam Yacht Club.
Jack was able to enjoy sailing the waters of Cape Ann for more than 80 years, through this October, when he sailed his sloop “QED” to winter storage. He especially loved sailing and racing one-design boats. Jack would sail alone, with family or with anyone who would enjoy going for a sail with him. Some regarded him as a master of light-air sailing in the tidal currents of the Annisquam River and in Ipswich Bay. When on shore, Jack greatly enjoyed family dinners and gatherings of four generations of Cunninghams.
He is survived by three sons and daughters-in-law, John D. III and Elise “Lee” Cunningham, Robert W. and Jean “Gigs” Cunningham all of Annisquam, David R. Cunningham and Leslie A. Perrell of West Nyack, New York, seven grandchildren, John D. “Tad” Cunningham, IV, Andrew C. Cunningham, Benjamin B. Cunningham, Peter N. Cunningham, Sarah F. Cunningham and Nathan C. Cunningham, Karim M. Ouazzi, four great-grandchildren, Aidan, Cole, Thea and Lyall Cunningham, and several nieces and nephews. He was also predeceased by his brother, Donald E. Cunningham.
His burial services will be held privately in the Oak Grove Cemetery. There will be a gathering for chowder in celebration of Jack’s life at the Annisquam Village Hall on Sunday, December 13th from 12:00 – 2:00 p.m. In lieu of flowers, expressions of sympathy may be made in his memory to the Gloucester Education Foundation, 183 Main Street, Gloucester, MA 01930 or Cape Ann Museum, 27 Pleasant Street, Gloucester, MA 01930.