David Pierre Chessey, 76, of Portland, Maine passed away peacefully on February 21, 2024. Son of Sylvia M Douglass and George E Chessey, he was born September 5, 1947 in Patuxent River, MD, the only son in a family of seven. His childhood was an idyllic time in his life, which he recalled fondly. His uncles and father taught him how to cut trees, hunt, fish and perhaps most importantly, show gratitude for the many friends and family that indulged his sweet tooth. He graduated from Cheverus High School in 1965, and was a member of the glee club and swim team. Despite the Jesuits' intentions for him to attend Juilliard as a pianist, he graduated from Merrimack College in 1969 with a Bachelor's degree in American History. It was in college that David was introduced to one of his many pastimes, the martial art of Judo. Shortly after graduating, he was drafted into the Army and served in the Vietnam War for 13 months. Upon returning from his duty in Vietnam, David's passion for helping people afforded him the opportunity to tutor a young boy, Wallace McWilliams Jr. in Sebago, Maine. It was this fortuitous relationship of teacher and student that provided the opportunity for David to meet Wally's oldest sister, and the future love of his life, Joan May McWilliams. Having grown up with four sisters himself, David had a deep appreciation for strong-willed, hard-working, and beautiful women. David, by all definitions, was a "tall man" with a tan from his time overseas. Coupled with his Eagle Scout honesty and integrity, it was love at first sight for both of them. David and Joan were married just four months later on August 5,1972, surrounded by family and friends at Saint Joseph's Church in Bridgton, Maine. In 1977, they were blessed with their first child, Serena. Four years later, they welcomed their second child, Angeline,and two years after that, their son Nathan. David was a devoted husband and father that never deviated from his commitment to his wife and family. In the midst of a growing family, David soon followed in his father's footsteps and was hired at the US Postal Service as a mail clerk. Never wanting to rely on his father's excellent reputation as a means to establish himself, David put his Jesuit education to the test and soon was managing more than just the mail. His easy-going, honest and reliable demeanor allowed him to be promoted quickly and successfully. In 2009 Dave retired from the U.S. Post Office as a Logistics Coordinator. While juggling the demands of a family, David continued his passion for martial arts by starting The Portland Judo Club, training multiple days a week at the police station. During his time with Judo, David earned a third degree as a black belt. When his younger children became members of the Portland Porpoise Swim Club, he managed the long hours and stiff back that accompany sitting still during swim meets, by becoming a nationally certified USA Swimming Referee and Official. Between swim meets, judo practices, and work commitments, David still found time to visit with his parents at their lake home on Hancock Pond; the Red Cottage. After a long day cutting, splitting and stacking wood, a dip in the pond with his kids, a game of chess with his dad, or a bowl of his mom's bread pudding made all the sacrifice worthwhile.​ David is predeceased by his sister; Rosalie, father; George Ephraim Chessey, and mother; Sylvia Marie (Douglass) Chessey. He is survived by countless nieces, nephews and cousins, as well as his sisters Claire (Chessey)Cotes, Joanne Chessey,and Suzanne (Chessey) Walton, and, his wife Joan May (McWilliams) Chessey, his children Serena Chessey, Angeline (Chessey) Marcotte, and Nathan Chessey, grandchildren, Autumn & George Gay, and Gwenyth & Orion Marcotte, and great-grandson Landon Izaiah Aponte Alvarez. During his nearly 70 years in southern Maine, David became a well-known fixture on the Judo mat, the pool deck, and in the Sebago community. David was an exemplary father and human being. He embodied the best of qualities: unconditional love, strength of spirit, and an unending generosity that could be seen in his care for his parents, his wife, children, grandchildren, entire family and countless others. A celebration of life will be held during the summer of 2024. Should you feel so inclined, you are welcome to make a contribution to the Maine Veterans Home of Scarborough A-Unit, whose incredible staff consistently went above and beyond to make sure his days and weeks were enjoyable, entertaining and peaceful.