Robert O. "Bobby" Humphrey, 71, passed away on July 24, 2020 at Boston Medical Center after an unexpected brain hemorrhage. He was born in Marblehead on April 11, 1949, son of the late Frank W. Humphrey, Jr and Elizabeth M. (Osborne) Humphrey. At a young age, he was always very inquisitive as to how things worked. He would often take things apart just to be able to put them back together. One story he told was getting an old lawnmower and making it into a go-cart and riding around the neighborhood. He was a graduate of the Clark School for the Deaf and St. Johnsbury Academy, St. Johnsbury, VT where he was an avid skier. In his earlier years he worked with a communication company making devices to assist the hearing impaired. Although he himself was hearing impaired, it was important to help others like himself and he truly had that gift. He was fortunate to be able to have his own businesses in the window installation business, a painting company and most recently as a handyman. He would fix almost anything and would do an excellent job. His carpentry skills were best used making beautiful tables, cabinets and lazy Susan's which he loved to give to friends. If it was not perfect, you could be sure that he would throw some paint on it and start all over again. He loved the Town of Marblehead and its history. A great snowy day would be spent with Carol playing the game "What's Not in Marblehead Anymore?" And they would reminisce of the town they grew up in. An avid pool shark he loved to play the game any chance he had. Not to win but to enjoy the game and share his skills with others. He was a member of the Gerry 5 in Marblehead and the Elks at Bass Rocks in Gloucester. The last 10 years he faced multiple medical issues but fought very hard and never gave up. Proved he was a Survivor. Two words to describe him, Kind and Loving. He is survived by his partner, Carol Clark of Gloucester; his sister, Suzanne Humphrey Ulrich and her husband, George of Marblehead; two nephews, Joshua and Matthew Ulrich and many cousins in the Osborne, Attridge, Russell, Graves and Kiely Families. At his request there will be no services. A Celebration of his Life will be announced at a later date when being social is safe. Contributions may be made in Bobby's name to the American Heart Association, 300 5th Ave Waltham, 02451 or Massachusetts General Hospital, 55 Fruit Street, Boston, MA 02114. Arrangements are by the Greely Funeral Home 212 Washington St. Gloucester.