MONMOUTH – Timothy Alan Jackson, 66, passed away at his home on Oct. 14, 2020 surrounded by his family, following a diagnosis of metastatic cancer in May of this year.

He was born in Augusta to Philip D. and Barbara E. (Weymouth) Jackson, of Winthrop, on Jan. 24, 1954. Timmy was the middle child, and the only boy in a family with four sisters. Perhaps this is how he honed his comedy skills, playing for an audience both older and younger than himself from the time he was in a highchair.

Of course, when he wasn’t cracking jokes and singing opera around the house, he could generally be found fishing with his family and friends.

While he wasn’t much of a scholar, he was the class clown and he made the most of school by blaming many of his antics on Kevin St. Hilaire.

After graduating from Winthrop High School in 1972, Timmy took up with Debbi Sylvester, a lovely daughter of Manchester, and made the best decision of his life in marrying her on Dec. 10, 1977 in a holiday themed wedding. After celebrating at Hazel Green’s, they spent a frigid honeymoon at a ski resort near Moosehead. In 1983, Timmy and Debbi moved from Winthrop to Monmouth, where they raised their family.

Their first daughter, Tori Lee, was born in 1978, followed in short order by Hannah Lindsay in 1979. After taking a bit of a breather, Heidi Rose came along in 1984, and (Timothy) Tyler rounded out the family in 1987.

Timmy held many jobs in his younger days, from working at My Brother’s Restaurant, selling 8-track tapes door-to-door, taking care of apple trees at Chick Orchards and working in refrigeration at Dumont Industries while the kids were young. But, being injured at that job might have been the best thing to ever happen to his career.

When he was forced by his injury to leave Dumont’s, Timmy decided to turn his side hustle into his main hustle. He had always tinkered with ice fishing traps, trying to come up with the best and most reliable design. He made and sold his first set in 1979 and this hobby ultimately became Jack Traps, Inc., the premier ice fishing outfitter in the northeast. He dedicated most of his life to Jack Traps, regularly working 80-hour weeks, rarely taking time off, even to fish. Timmy sold the business in 2019 and Jack Traps will remain a landmark in Monmouth and in Maine for years to come.

One of his proudest achievements was creating the Annual Youth Ice Fishing Derby sponsored by Jack Traps, to which countless local businesses and volunteers contributed time and resources to get kids out on the ice. Thanks to his idea and efforts, thousands of local kids tried ice fishing for the first time. This non-competitive event brought families out for a fun day on the ice and no child left empty-handed. His favorite part of the day was the drawing for lifetime fishing licenses. In 2019, they were able to give away twenty of these to local kids who will know the joy of being in nature, in part, because of him.

Along with fishing, Timmy’s father also helped instill a lifelong passion for gardening. From huge beds of Sweet Williams sold to local flower shops to dozens of tomato and pepper plants and everything in between, he was meticulous about caring for his gardens and enjoyed using his father’s tips and “secrets” to get the best results. Though the kids didn’t always appreciate having to weed and harvest vegetables at the time, it became one of the many ways Timmy taught them about the value of hard work.

Always one to wheel and deal, Timmy enjoyed buying and selling boats for fun. He had quite a few over the years, eventually deciding to keep a nice Sylvan fishing boat, which he outfitted for the ideal day of fishing. He even acquired a boat he’d been chasing for years, a 20-foot Corson, just this summer.

Perhaps one of Timmy’s greatest joys was becoming Grampy to five grandchildren. Lilah, Peyton, Beckett, Violet, and Sawyer each had a very special relationship with their grandfather, where he passed down some of the same lessons about making traps, gardening, stacking firewood just right, and the funniest prank shows to watch on television. Timmy’s particular brand of humor can often be seen in his grandchildren. Fishing with Grampy, which they were able to do one last time in July, was one of the most sought-after adventures of all!

Timmy was predeceased by his father, Philip D. Jackson and mother, Barbara E. (Weymouth) Jackson, both of Winthrop.

He leaves behind his wife of 43 years, Deborah S. Jackson of Monmouth; daughter Tori Lee Jackson and her husband Michael T. French of North Wayne; daughter, Hannah Lindsay Jackson, her husband David B. Hall and their children Lilah Grace, Beckett Philip, and Sawyer Benjamin of Durham; daughter, Heidi Rose Jackson, her partner Tanner Kelleter, children Peyton Emma and Violet Ann, and their father, Luke McDonald all of Monmouth; son, (Timothy) Tyler Jackson of Portland; sister, Deborah King and her husband Gerald King of Winthrop, sister, Rebecca Gillespie and her husband William Gillespie of Winthrop, sister, Betty Stevenson and her husband Craig Stevenson of Wayne, sister, Cathie Poulin and her husband Larry Poulin of Readfield; brother-in-law, Brian Sylvester and his wife Debbie Sylvester of Southport, sister-in-law, Jane S. Kemmerer and her husband James Kemmerer of Holderness, N.H., sister-in-law, Susan S. Murphy of Augusta; numerous nieces and nephews; many wonderful cousins (including the Prebles); good friends, and fishing buddies. Timmy will be missed by so many and for many reasons.

We’ll see you next summer on the ice?

There will be a private burial at Lakeside Cemetery in Winthrop. The family hopes to (safely) host a large gathering in the spring to bring together all who knew and loved Timmy and send him off in style.

Arrangements are by Roberts Funeral Home and Cremation Care, 62 Bowdoin Street, Winthrop. Condolences, memories, and photos may be shared with the family on the obituary page of the Roberts Funeral Home website: http://www.familyfirstfuneralhomes.com.

In lieu of flowers,

please take a young person in your life fishing

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