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James W. Gain
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Obituary for James W. Gain

WESTBROOK – James W. “Jim” Gain, 66, passed away after a short illness on June 25, 2018, with his family by his side.

Born in Portland on January 12, 1952, Jim was the son of the late Harold and Violet (Graham) Gain. He spent most of his early life in Fryeburg and graduated from Fryeburg Academy Class of 1970. Throughout his life, he maintained his love of Fryeburg, and enjoyed spending time there. He knew the town like the back of his hand, and fondly remembered riding his bicycle 25 miles a day with his childhood friends.

When Jim moved from Fryeburg, he attended SMTC to become a certified master auto technician. For over 20 years, Jim worked in multiple dealerships throughout the greater Portland area.

Jim married the love of his life, Jessie Sanders, on June 12, 1976. Together, they made their home in South Portland where they raised their son, Dave. Jim and Jessie recently celebrated their 42nd Anniversary.

In his prime, Jim had a larger than life personality. He was the life of the party, loved to joke, tease and have fun. In his later years, medical conditions may have settled down a bit, but he never lost his sense of humor. He was a humble man who enjoyed the outdoors and hiking. Baldface Mountain in New Hampshire was a particular favorite. Jim also welcomed a good game of chess or pool, and always loved spending time with his family and friends.

It’s said that the purity of a person’s heart can quickly be measured by how they regard animals. In Jim and Jessie’s case, their hearts were huge. Throughout the years, they rescued several dogs and cats, giving them a loving home.

Jim will be remembered as a gentle, caring and kind person who loved to pass on his knowledge to others. When his grandchildren came along, he became a “big lap” grandpa who would do anything Ellie and Violet wanted, even watching Barbie. He was a proud and supportive father to Dave, and a loving and caring husband to Jessie.

He is survived by his beloved wife of 42 years, Jessie Gain of Westbrook; son, Dave Gain and wife Bethany of Gorham; his adored granddaughters, Violet and Eleanor ; and many extended relatives and friends.

The family would like to extend a sincere thank you to the first responders of the Westbrook Fire Department who cared for Jim when he suffered his stroke on Sunday.

Visiting Hours celebrating Jim’s life will be held on Sunday, July 8 from 1-3PM at the Conroy-Tully Walker South Portland Chapel, 1024 Broadway, South Portland.

In lieu of flowers, memorial contributions may be made to the Harvest Hills Animal Shelter by visiting

To send flowers or a remembrance gift to the family of James W. Gain, please visit our Tribute Store.

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Visiting Hours




1:00 PM - 3:00 PM
Conroy-Tully Walker Funeral Home - South Portland Chapel

1024 Broadway
South Portland, ME 04106


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