Randy Jackson

Randy Jackson passed away on May 19, 2025 after a valiant fight against cancer at the University of Maryland Hospital in Baltimore. He was surrounded by people who loved him: his daughter Holly, his girlfriend Rose, and his best friend Chip.

Randy was born on June 27,1949 in Kittery, Maine at a naval hospital to Ralph Fielding Jackson Sr. and Joann Pinkerton Jackson. Ralph Sr. was a naval captain whose career took the family around the US and abroad. Randy had an older sister Tracy Jo, a younger brother Timothy Charles, and a younger sister Melissa Ann. Randy lived in many beautiful and interesting places around the world, including Hawaii, Arlington, Falls Church, Puerto Rico, Scotland, San Diego, Mystic and Newport. He attended St. Andrews in Barrington, RI, and graduated in 1967. At this boarding school, he was editor of the yearbook, active in sports, and the only boarder to have his own room. He went to college at Old Dominion College in Norfolk, VA, and graduated in 1972. It was there that he met his best friend Chip Walsh along with several other lifelong pals.

Randy was briefly drafted to the U.S. Army. After his service was complete he found roots in Maryland where he stayed for the remainder of his life. During this period he met, Bobbi Hubans Jackson, whom he married in 1979. In 1988, they had a daughter, Holly Joann, who now resides in Brooklyn, New York. Randy and Bobbi stayed together for two decades.

Randy’s life was deeply shaped by his school years in Scotland where he first heard the Beatles and developed a love for soccer. Those passions remained instilled in him throughout his life as Randy played in a soccer league until the age of 52. He was an avid fan of the Baltimore Orioles, the Washington Commanders, and DC United soccer.

Through the friends Randy made in college, he learned to party and enjoy life. He loved drinking beer and making people laugh. Randy’s jokes were unmatched. He had a playful nature and could lighten the mood of any room. Randy loved to garden and was known for his immaculate lawn. He had a curiosity for the stars, he sought out meteor showers and witnessed three solar eclipses in totality. He enjoyed many of these activities with his girlfriend Rose Overturf, with whom he spent the last 18 years of his life.

Randy found meaning through acts of service, frequently helping his friends with home projects, which earned him the nickname “handy Randy”. He helped his best friend build his first house and supported his daughter with multiple renovations. Randy’s wicked wit combined with his willingness to lend a hand made him a great friend to many, and he will be fondly remembered.

A celebration of life will be held on June 28 at 11:00 AM at John M. Taylor Funeral Home in Annapolis, MD. In lieu of flowers, consider making a donation to the World Central Kitchen.