Harold E. Massey, Sr., 87, passed away peacefully on April 16, 2026 at his home in Suffolk, VA, surrounded by his loving family.

Above all else, Harold Eugene Massey, Sr. was a man of God. While he could tell you everything about a truck’s engine, he was even better at sharing the Good News. For 50 years, he served the Salvation Army with a servant’s heart, first in Newport and later in Portsmouth. His life was a testament to the fact that when you love the Lord, every road leads home.

Harold Eugene Massey, Sr. began his journey on January 9, 1939, born to Milton Coyle Massey and Alfaretta Gaines at 25 Burnside Avenue in Newport, RI. A man who truly understood the meaning of a “long-haul” commitment, Harold shared 56 wonderful years of marriage with his wife, Brenda, and built a legacy that would require a fleet of his favorite trucks to move.

Harold’s work ethic was the stuff of legends. He spent over 50 years with Safeway of Newport (now Waste Management), earning countless awards for his dedication. Rain, shine, or even a case of the sniffles, Harold was at the wheel. He was a “jack of all trades” who mastered everything he touched, but his heart truly belonged to anything with an engine. His massive collection of cars and trucks was his pride and joy—second only to the family he steered through life.

However, the true “North Star” of Harold’s life was his profound love for the Lord. A devoted soldier of the Salvation Army for over 50 years, Harold didn’t just attend church; he lived his faith. Whether he was serving as the Treasurer of the Newport Corp or continuing his ministry with the Portsmouth Corp in Virginia over the last eight years, Harold was a man on a mission. He loved the Lord with a passion that eclipsed even his favorite vehicles, often saying that while his trucks were his hobby, Jesus was his foundation. He was a humble servant who found joy in the hymns, the fellowship, and the simple act of being in God’s house.

Harold is survived by his wife, Brenda P. Massey; six sons: Lonnie (Diane), Austin, TX, Kevin (Wilma), Providence, RI, Dwayne, Providence, RI, Keith (Louisa), Westport, MA, Travis, Stoughton, MA, and Eric (Son-In-Love), Suffolk, VA; and three daughters: Belinda (Greg), Apex, NC, Darcene, Suffolk, VA, and Michelle (Tim), Covington, GA.

He was preceded in death by his son, Harold E. Massey, Jr. (Maine). Harold also leaves behind his 92-year-old twin sisters, Floretta Sheffield and Lorretta Massey, along with a remarkable 27 grandchildren, 50 great-grandchildren, and a host of nieces and nephews who will miss his sense of humor and big heart.

In lieu of flowers, please consider donating to your local Salvation Army in honor of Harold’s generosity and his love of giving to others.  Cremation Society of Virginia, Chesapeake Office, is assisting the family at their time of need.  Friends and family may share online condolences and memories at www.vacremationsociety.com

A service and home going celebration of Harold’s life will be held at the Salvation Army located at 2306 Airline Blvd., Portsmouth, VA  23701 on Saturday, May 30, 2026 at 11:00 a.m.  Friends and family are invited to attend and pay their respects.