Herbert Lorenzo Rayne's Obituary
Herbert “Squeaky” Rayne passed away on December 28, 2025, at Atlantic General Hospital in Berlin, Maryland. He was 68 years old.
Born on May 14, 1957, Herbert was the son of the late Gladys Rayne and Sunny Wescott. He grew up as the only boy among seven sisters, a role that helped shape the humble, caring, and people-loving man that so many came to know and love.
Herbert attended Indian River High School before beginning a lifelong career in the handyman industry. Known by many as a true “Mr. Repairman” and a “Jack of All Trades,” there was rarely anything he couldn’t fix—or at least tinker with until it worked. He took pride in hard work and wasn’t afraid to do whatever it took to get the job done. Over the years, he worked for Showell’s in Bishopville, Allen Lathbury’s, and Jay’s Market, always lending his skills wherever they were needed.
A natural tinkerer, Herbert was happiest with tools in his hands, especially when working on his beloved 1957 Chevy, which he cherished and enjoyed restoring. His work ethic was matched only by his generosity—he would give you the shirt off his back without hesitation.
Herbert loved everyone. He was a people person through and through, always humble, always ready with a joke, and always willing to help others. His kindness, laughter, and willingness to lend a hand left a lasting impression on all who knew him.
In addition to his parents, he is preceded in passing by his sisters: Patricia Sykes, Frances Rayne, Rose Dixon, and Sandra Aimes; and his brother, James Dixon, Jr. He is survived by his sisters: Gladys Hopkins, Vanessa Dixon, Charleen Major (Wayne), Ida Mitchell (Kevin), and Janice Dixon Willis; his step children: Ronnie, Jackie, and Elizabeth Leak, and Norwood Whaley; his companion of over 20 years, Mary Louise Leak; his great grandchild, Makiyah Cottingham; his Aunt, Linda Cooke; a host of nieces, nephews, and extended family; and his close friends, Joe Rogers and Kenny Postley. The family would also like to extend a special thank you to Silver Lining Healthcare and its dedicated staff for the compassion, care, and support they provided while taking care of Herbert.
A Viewing will be held on Friday, January 16, 2026, from 10:00 AM to 11:00 AM at Watson Funeral Home & Crematorium, 211 S Washington Street, Millsboro, DE with a service to begin at 11:00 AM. Burial will follow services at Zoar Golden Acres Cemetery in Bishopville, MD.
Please visit Herbert's Life Tribute wall and sign his online guestbook at this site.
FLORIST NOTE: PLEASE HAVE ALL ARRANGEMENTS DELIVERED TO WATSON FUNERAL HOME, MILLSBORO, ON THURSDAY, JANUARY 15, 2026, BY 2:30PM
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