James E. Toland

James E. Toland passed away peacefully on December 29th, 2025 surrounded by family and friends after a courageous 18-month battle with cancer.

Jay was born in New London, CT on November 19th 1973, to Thomas and Paula Toland. They lived in Mystic and later moved to Preston, where he grew up and made a lasting impression on the many friends he made. As a child, Jay rode BMX, but not ever as well as his sister, Tara. Despite suffering a broken arm in one race, he still managed to finish near the top of his division in New England.  He also played youth football for Ledyard after getting scolded by Tiger for almost not making weight.

Jay had several jobs throughout his life working for a lobster boat, Pepsi, Preston Trading Post, Cargill, and Scott’s Miracle-Gro; making lasting friendships along the way. He also started his own businesses including “Fat Daddy’s Backyard Barbeque”, “Jay Potts LLC”, and “Canterbury Cuts”.

Jay welcomed his best friend and son, Hunter James, to the world on March 23rd, 1998.  From that moment on, the two were virtually inseparable.  The incredible bond they had led to innumerable adventures together, even some a father and son should probably not have had.

In 2004, he connected with the love of his life, Karen – his rock, his strength, and his constant – who never left his side throughout his courageous battle with cancer. Jay and Karen married on October 8th, 2005, joining their families under one roof. They moved to Canterbury in August 2012, building a life they both loved together. Besides Hunter and Tyler, Jay had many fur-children whom he loved dearly.

Jay had many hobbies from playing his daily numbers, buying his scratchies, betting on all kinds of sports, playing poker with all his poker buddies, playing scat with his second family at the American Legion (“the Leeg”), and playing pitch with his family. However, his true passion was always hunting. Every September you could bet he’d be in his camo for bird hunting with his “kids”. In November, he’d either be deer hunting at Glenn’s, the family cabin in upstate NY, or out a passenger window. Jay loved spending time at the cabin, whether it was for hunting or to go party with the guys. Per usual, Jay made so many friends that are now considered family in NY. This past May, he was able to endure a Canadian bear hunt with Quad B Outfitters. Jay and the rest of the T&T brotherhood (Hunter, Steven, and Ryder) enjoyed a trip that will never be forgotten.

Despite facing impossible odds, Jay never lost his zest for life, he was truly one of a kind. Smart, opinionated, and funny; a friend recently described him as loud, larger than life, usually inappropriate, but with a huge heart.  Although Jay’s life was cut short by this terrible disease, he enjoyed his life tremendously with family and friends, his hobbies and passions, and always with a Busch Light in hand.  Jay will be sorely missed by the countless lives he touched along the way.

Jay was pre-deceased by his father, Thomas “Tiger” Toland. He is survived by his mother Paula G. Toland; wife Karen; sons Hunter (Miranda Hatch) & Tyler Fleming (Ashley); sister & brother-in law Tara & Todd Bolles; brothers Tom Jr. (April), Shaun, & Justin (Samantha); grandchildren Rylan & Emersyn Fleming, with one more due in January; Nieces and Nephews Ava, Brooke, Aleah, & Carter; father & mother-in-law “Fast” Fred & Marion Fleming; brother-in-laws Eric & Mike Fleming; and cousin/best friend Steve Tardiff (Cheryl).  He is also survived by the Toland, O’Brien, Bolles, and Fleming families; his childhood bestie Tommy Gauthier (wife Jenny); his adult bestie Jim Nault (wife Darlene); and numerous friends he loved fiercely.

A very special thank you to his angels, the staff at the Plainfield Infusion Center. We really can’t thank you enough for the care you gave to Jay. You are all amazing people.  Additionally, thank you to Jay’s daughter-sister-wife Miranda (Hunter’s future wife) who took Jay to most of his appointments and on special dates. We could not have gone through the journey without her.

Calling hours will be held on Friday January 9th, 2026 at Gagne-Piechowski Funeral Home (490 Voluntown Rd Griswold, CT 06351) from 5 p.m. to 7 p.m. A celebration of life will be held at the Windham American Legion Post 19 (339 Brick Top Rd Windham, CT 06280) on Saturday January 10th, 2026 at 12pm.  In lieu of flowers, donations can be made in Jay’s name to American Legion Post 19.

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