Harold H. Diggs, Sr.

Harold H Diggs Sr. was born in Boston, MA on November 1, 1935 to Grace M Diggs of New York and Edwin Diggs of Boston, MA. He was the youngest of “Mama and Dada’s” four children, all of whom preceded him in death, including Edwin Diggs, Clara Diggs, and Alfred Diggs. Ralph Diggs (living), the son of Clara, was also considered a sibling; he was raised by Harold’s parents.

Harold married Leona Pritchard in July of 1954. From their union came four children:  from eldest to youngest, Harold H Diggs Jr. of Union City, GA; and Grace V Diggs, Michael A Diggs, and Kevin L Diggs Sr., all of Boston, MA.

Harold was an automobile mechanic by trade; he graduated from Boston Trade School.  He enjoyed fixing cars and spent the better part of his career working for Chevrolet Dealerships as a mechanic. When not at the dealerships, he could be found around the neighborhood working on repairs for family and friends. Later in life, he worked in several different positions for Boston Edison, from which he retired. He also loved to fix and maintain his long-time home in Roxbury.

Harold loved the outdoors. In his younger years, he enjoyed hunting with his sons, as his wife and daughter looked on. He was also a veteran fisherman and spent many years traveling back and forth to Gloucester, MA on deep sea fishing expeditions with his best friend, Glenwood Gray, aka “Gray”, who preceded him in death in October 2018. Harold loved his Gloucester family and Gray’s family was like his own. His favorite pastimes were sitting outside on the back steps to his home, chatting with all the passers-by, and hanging out in his “special room” listening to music. Harold loved Anita Baker, Mahalia Jackson, and Noel Pointer, to name a few. He also was a story teller and shared many tales of not just his travels throughout the world, but about his childhood, his family growing up, history, and politics. He always had lots to say about his brother Edwin who was in the service during WWII.

Harold is survived by his children and their mother, and by his grandchildren, including Charlene P Hobbs of Fairburn, GA; Nina L Diggs of Stoughton, MA; Elisa V Smith, Kevin L Diggs Jr., Dustin M Williams, and Terrence A Pearson, all of Boston, MA. He is also survived by a host of great grandchildren, cousins, nieces, nephews, and friends. We will all miss him dearly.

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