John Joseph Szymaszek III

John Joseph Szymaszek III passed peacefully at Middlesex Hospital on February 25, 2026 surrounded by his family.

"Jack" was born August 29, 1943 in Middletown, CT. He was the 2nd of 3 children born to John J Szymaszek Jr (Meriden) & Mary Bajorek Szymaszek (Portland). Jack attended school in Portland and was one of the very first "virtual learners". He attended 2 years of middle school via intercom from his home while battling nephritis. He was a proud Highlander and graduated from Portland High School in 1961. After which he joined his father for a short time working at Standard Knapp, then started a life long career with Southern New England Telephone Company where he worked for 33 years in various roles, most notably in the payphone division as a coin collector. After retiring from SNET he worked part-time driving school bus for Nichols bus service where his kids affectionately referred to him as "Bus Driver Jack".

Jack met the love of his life Nancy Denman in June 1962. They were married on September 19th 1964, and started their lives together in East Hampton where they raised 2 boys, John J Szymaszek IV and Todd Wayne Szymaszek. Being a father is where Jack shinned!! His family was the heart & soul of his life. He and his boys did everything together—sports, outdoor activities, and swimming at their home on Lake Pocotopaug. After a family trip to Disney in 1976, Jack even built the boys a Castle in the backyard.

Jack was an outdoorsman, as a youngster he often hunted and fished the fields & streams of Portland. In East Hampton he was an active member and former President of the Belltown Sportsman's Club enjoying hunting & fishing with his boys. Additionally, he was avid boater, member & former Commodore of the Middlesex Yacht Club. Jack loved to travel and took countless vacations with his family and friends. He especially loved cruising with his grandchildren.

Jack is survived by his loving wife Nancy, his son Jay & wife Barbara of Portland, son Todd & wife Dawn, granddaughter Amanda & grandson Luke of Orange, and his brother Gary & wife Margie of Mansfield. He is predeceased by his father & mother Jack & Mary Szymaszek and his sister Barbara McHugh.

In addition Jack leaves behind countless friends who will miss him dearly.

Per Jack's wishes there are no planned services.

The most important thing to Jack was his family & his friends. His wish was that he will live on in our hearts.