Thompson (Tom) Smalley

Obituary

Thompson “Tom” Smalley, 86, of Manchester-by-the-Sea, Massachusetts, died September 18, 2026, after a brief illness.
Born in Portland, Maine, on May 16, 1940, to Mildred and Lewis Smalley, Tom graduated from South Portland High School and the University of Maine at Orono.

In 1965 he married Rachel Boucher, and together they raised two daughters. They later separated after more than 22 years of marriage. Beginning in 2009, he shared a deep relationship with Sue Jackson, who understood him in a way few others did.

After a brief stint as a high school math teacher, Tom entered General Electric’s management program. A born entrepreneur, he wanted to work for himself. After working a few years for GE and then MEDITECH, he and two partners founded the Urethane Processing Corporation of America (UPCOA) in Beverly. After its sale, he founded Jenline, a related company named for his daughters. Based in Gloucester, Jenline manufactured the widely used Soothie pacifier, among other products. Tom operated the company until selling it to a German firm. He was justifiably proud of what he had created.

Often described as an “old salt,” Tom was smart, energetic, witty, generous, impatient, irascible, sentimental, and thoroughly unpretentious. A great storyteller with an infectious laugh, he was never afraid of embarrassing himself or occasionally being inappropriate, and he regularly got himself into (and, fortunately, out of) trouble. He leaves mountains of stories that will be told, and likely embellished, for generations.

An adventurer, Tom skied, rode motorcycles, was a small-plane pilot, went skydiving and bungee jumping, and visited every continent, but sailing was his greatest passion. A self-taught sailor, he owned several boats over the years, naming each one Olde Thompson. As a member of the Jubilee Yacht Club, he won races from Maine to Bermuda. In November 1994, the Swan 41 he had long dreamed of owning caught fire enroute to the Caribbean, forcing the crew to abandon ship. After being rescued, Tom fortuitously found another boat just like it. The replacement already bore the name Joss, which he kept, deciding it stood for “Jump Off, She’s Smoking.”

Tom was endlessly curious about people. He remembered numbers and dates, but people’s stories mattered to him most. Friends and family often sought his excellent advice. He encouraged his daughters to work hard, prioritize family, and seek meaning beyond material success, and he never hesitated to express his love and admiration for those closest to him. He was always in our corner, even when he didn’t quite understand what that corner was all about.

His grandchildren adored him, and he adored them. Watching those relationships flourish brought his daughters tremendous joy. For all his professional success and adventures, Tom understood that his family was his proudest accomplishment. His final hours were spent surrounded by his daughters, Sue, his grandchildren, and a few close friends who made sure he knew he was loved and not alone.

Tom is survived by his daughters, Jennifer Kaufman and her husband, Doug, of Storrs, Connecticut, and Caroline O’Brien and her husband, Conor, of Pepperell, Massachusetts; his grandchildren, Rebecca and Emily Kaufman; and Kylie, Benjamin and his wife, Rita, Finian, Jonathan, and Tobias O’Brien; his longtime partner, Sue Jackson; his brother, Lewis H. Smalley, and his wife, Diane; his former wife, Rachel Smalley; numerous nieces and nephews; and more friends than can be named. 

He was predeceased by his parents; his sister, Donna Rae Craine; and his grandson, Liam O’Brien.

A celebration of life will be held in the late fall or early winter.  In lieu of flowers, please raise a toast to Tom, set out on an adventure, share a good laugh, or enjoy a lobster, ice cream, a Diet Coke, or a cigar in his memory. 

Gallery

Memory wall

Celebration of Life