John W. "Jack" Estes, Jr., 83, of Westbrook, Maine, passed away peacefully on July 15, 2025, at his apartment at the Gorham House. Jack was predeceased by his beloved wife Mary Helen Estes, his brother Ronald Estes, and his parents, John W. Estes, Sr. and Marion Estes. He is survived by his two sons: Bill and wife Gail Estes of Avondale, PA, and Jeff and wife Kelly Estes of Hollis. He was a proud grandfather, affectionately known as "Bumpa" to his grandson, Luca Estes, and granddaughters Elaine Garton and her husband Dave, Elise Estes, and Elizabeth Estes. A 1960 graduate of Westbrook High School, Jack embodied his yearbook ambition "To be a success" through a life of service, integrity, and community involvement. He was an active student — a member of the National Honor Society, President of the Key Club, Treasurer of the Science Club, participant in multiple sports, and, to the amusement of many, President of the Driving Club. Jack began his professional career as a banker and, after 1989, found meaningful work with the Westbrook School Department and the Portland Sea Dogs. In retirement, he filled his days with what he cherished most: friends, family, and travel — including cruises and trips to Las Vegas, Arizona, Foxwoods, Oxford, and Bangor. He never missed a chance to watch his family's sporting events, even the ones he didn't quite understand, and remained a diehard fan of all things Chicago sports. His high school quote, "The highest distinction is service to others," became a guiding principle in his life. Jack dedicated years to public service, including terms on the Westbrook City Council and School Committee. He gave his time generously as a volunteer at Mercy At The Fore and in the Barbara Bush Children's Wing at Maine Medical Center. He was also a proud and active member of several charitable organizations, including the Westbrook Lions Club, the Eagles, and the Knights of Columbus. Jack was a true son of Westbrook to the very end — civic-minded, spirited, and full of humor. As many in the community have fondly noted, he may well have been the only unofficial mayor the city ever had. The family wishes to extend heartfelt thanks to the compassionate staff at Gorham House, to the nurses and caregivers from Compassus Hospice for their outstanding care and kindness and the many friends who brought him into their families and offered their help. Friends and family are invited to attend a time of visitation on Saturday, September 13, 2025, from 9:00 to 10:00 a.m. at Dolby, Blais & Segee Funeral Home, 35 Church Street, Westbrook, followed by a memorial service at 10:00 a.m. Interment will follow at St. Hyacinth Cemetery. There will be a Celebration of Life gathering from 12-2 p.m. at the Stockhouse Restaurant, Westbrook. In lieu of flowers, donations in Jack's memory may be made to MaineHealth Barbar Bush Children's Hospital, https://fundraising.mmc.org/bbch-donate-now.