Robert (Bob) M. Maddestra passed away peacefully on November 21, 2023, at his home in Canton, MA surrounded by his loving family. The beloved husband of Ilona (Susan) Maddestra (Saulle) for 47 years, they built a life and home filled with love, laughter and open doors for all. He was the son of the late Domenic and Rose Maddestra. He was a devoted father to Robert Maddestra Jr. of Narragansett, RI, Michelle Pijewski and her husband Stanley Pijewski of Norton, and Cynthia Maddestra of Canton. He was the loving grandfather of 8 grandchildren, in which he took great pride and pleasure in celebrating their accomplishments and milestones - Nichole Woods and her husband Jeffrey Woods, John Kilcommons and his wife Melanie, Abigail Perry, Carissa Perry, Ava Perry, Ella Dorsey, Francesca Maddestra and Alex Maddestra. Bob was also the adoring great-grandfather of Trevor, Brynn and Sawyer. He was the dear brother of Frank Maddestra of Scottsdale, AZ and the late Carmen Maddestra. Born and raised in Hyde Park, MA, Bob graduated from Boston Tech and went on to receive a full scholarship to Mass Art Institute. However, he decided to take a full time position at Damon Corporation as a drafting engineer. As a result of his tenacity and work ethic he was promoted to Director of Operations. In 1989, he then founded DCM Instructional Systems. Bob was a man of faith as well as a parishioner at St. John the Evangelist Church in Canton. His faith guided him throughout life. Christmas Eve was his favorite holiday with loved ones. He enjoyed the Italian tradition of preparing the feast of seven fishes, especially his signature Calamari. He looked forward to the summer days; participating in his family’s annual Smigliani Horseshoe Tournament and hosting his yearly 4th of July barbecue. His love for his family was the center of his heart. He treasured time spent traveling with his wife and friends. Most memorable - his unforgettable trip to Italy, and multiple Disney vacations with the grandchildren. He was fond of the nights spent with his friends; enjoying laughter, poker, cheering on the Patriots and a glass of wine. He would love to challenge his family in a game of scrabble while talking about the good old days. He will live in our hearts forever. Relatives and friends are invited to attend a funeral Mass at St. Oscar Romero Church, Canton, MA on Monday morning, November 27th at 10:00 a.m. Burial to follow at Knollwood Memorial Park, Canton, MA. Donations may be made in his memory to the Michael J. Fox Parkinson’s Foundation at http://www.michaeljfox.org
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