Robert William Gilman, Sr. Westbrook/Gorham - Robert (Bob) W. Gilman Sr., passed away on March 19, 2023. He was born on August 21, 1939 in Westbrook, the son of William and Helen (Hines) Gilman. He was the oldest of four kids - Anne, John and Catherine. He attended St. Mary's School in Westbrook and graduated from Cheverus High School in 1957. After graduation, he joined the Air Force and served until 1962 working on KC-135 Stratotanker as an airplane mechanic. On February 14, 1958 he met Carolyn (Horr) Gilman at a Valentine's Day dance in Westbrook. They started dating and were married on July 14, 1962, they were blessed with 5 children. Bob had two careers - from 1963 - 1988 he was a route salesman for Kirschner Meats and then LePage Bakeries. His route was in his hometown of Westbrook where he was fondly known as the breadman. In 1989, he became a custodian for the Westbrook School Department and was lead custodian at Westbrook Middle School where he worked until his retirement in 2005. Bob was beloved by the kids, teachers and staff at the middle school - they dedicated a yearbook in his honor. During his tenure at Westbrook Schools he also served as the chief labor negotiator for all school support staff. After he "officially" retired he continued to work at Westbrook School Department part time until 2018. Bob was very dedicated to work but his pride and joy was his family. He could be found at any of his kids' activities or sporting events when they were growing up, coaching many Westbrook youth along the way. He was also an avid golfer who could be found on the golf course every Sunday for the last 50 years with his good friend Wayne Neptune. Bob was predeceased by his son, Robert Jr., his sister Anne, his brother John, and grandson Grant. Bob is survived by his wife of 61 years, Carolyn, daughter Jenifer (Larry Parent), sons Tim (Debbie), Matt and Ben (Jess), sister Catherine (Paul) Reynolds, grandchildren - Mary Beth, Joel, Brittany, Corey, Adam, Jayden, Annabelle, Fenton, Lilly and John, great-grand children - Bastion, Eben, Beckett, Coen and Clara and many nieces and nephews. Family and friends are invited to attend visiting hours from 4-6 pm on Monday, March 27 at Dolby, Blais and Segee funeral home at 35 Church St, Westbrook. A funeral service will be held at 11 am on Tuesday, March 28 at St. Anne's Catholic Church at 299 Main St, Gorham.