David I. Chichester

David I. Chichester 1937-2026

Scarborough, ME - David Ira Chichester, the beloved only child of Ira K. Chichester and Marion E. Lappine, passed away unexpectedly but peacefully on March 3 at age 88. Raised in Amityville and Baldwin, NY, he graduated as Baldwin High's class president in 1955 and was voted "Most Likely to Succeed". Two months later he did, marrying the love of his life, Elaine Freeman. After graduating from Trinity College in Hartford, CT in 1960, he built a distinguished 30+ year career in the insurance industry. Beginning with Connecticut General Life Insurance Company, he spent 20 years helping pioneer dental insurance as a mainstream employee benefit. In fact, the dental claim form Dave designed is still in use. That same entrepreneurial instinct led him to co-found APS, a computer hardware and software company providing online dental claims billing, new at the time. To the very end of his life, technology was a particular joy as he embraced every new gadget and innovation with the enthusiasm of someone decades younger. In 1994, he retired as Vice President of Benefits and Administration at Phoenix Mutual Life Insurance Company in Greenfield, MA.

Dave was an amazing conversationalist. His warmth, enthusiasm, and insatiable curiosity led to instant rapport with anyone he met. He was well-known as a mentor and a fun boss. Dave gave generously to his community across decades of volunteer service. While living in Conway, MA from 1981-2017, he served on the local boards of Health, Planning, and Emergency Management. He was the voice of the town's reverse 911 message. While still working, Dave had served on various boards of Baystate Franklin Medical Center including Ethics, Finance, and Audit. His favorite role, however, was as an ER volunteer, where he held patient's hands, fetched blankets, and emotionally supported the clinical staff for 16 years. His final role was on the Greenfield Planning Board. In 2018 at a ceremony attended by hundreds, he received the Greenfield Recorder's Citizen of the Year award honoring his decades of service to so many civic organizations including Arena Civic Theater, Pioneer Valley Symphony, Reinventing Justice Project, and various social service and domestic violence programs. He truly believed helping others is powerful medicine for improving one's own well-being.

In 2017, Dave and Elaine moved to Greenfield, MA where they resided until moving to the Enclave in Scarborough, ME in November 2024. Dave and Elaine enjoyed many lifelong friendships. They had grown up sailing on Long Island Sound in NY and for 15 years, they chartered a sailboat with friends and family each February in the Virgin Islands. With a deep love of (loud) pipe organ music, Dave delighted in attending Kotzschmar organ concerts in Portland. In the mid-90s, his son Craig took him to Americade in Lake George, NY which resulted in Dave quickly buying his first Honda Goldwing, to Elaine's surprise. He and Elaine took many motorcycle trips, including to eastern Canada and the Great Smoky Mountains, riding until he was 80. They also enjoyed trips to Alaska, Bali, England, the USSR, the Dominican Republic, and most recently to Iceland. Other hobbies included photography and designing and maintaining extensive flower gardens.

After a health crisis in his early 60's made Dave acutely aware of how lucky he was, he focused on being thankful for each day. When his precious Elaine predeceased him after 69 years of loving marriage, he didn't know how he could live without her. But, as usual, he continued to engage with friends and develop new interests.

Dave is survived by son Craig and wife Marybeth Chichester, daughter Debbie and husband Douglas Baker, grandson David Baker and wife Jenna Ronbeck, granddaughter Jocelyn (Baker) Sawaji and husband Chinmay Sawaji, and treasured great-granddaughter Suraiya Sawaji. Nieces Kathleen Cotroneo and Christy DiGiovanni will miss their frequent phone calls. Devoted family and so many friends both new and old will miss his cheerful nature and his kidding.

There will be a private celebration of life in the summer. Dave believed in local charity. Anyone wishing to make a donation in his name could send it to FOKO.org (Friends of Kotzschmar Organ), PKD Foundation (PKDCURE.org polycystic kidney disease), or a charity of your choice. To share memories and condolences with the family, please go to: hobbsfuneralhome.com/obituary/david-chichester