Leonard Derrill Hollifield II

February 1, 1953 — March 31, 2026

Unionville

Leonard Derrill Hollifield II (“Derry” to family and close friends) passed away on March 31, 2026, in Unionville, Virginia. Derry was preceded in death by his wife of 44 years, Chantal (2020); his daughter, Christine (2015); and his daughter Jennifer (2019). He was also preceded in death by his parents Leonard and Dorothy (Dottie) Hollifield; brother Dennis Hollifield; brother Duane Hollifield; and sister-in-law Carole Dassonville. Derry is survived by his daughter Michelle Clark (Robert) of Unionville; his grandson Jared Jones (Danyelle) of Ashburn; his brother David Hollifield (Karen) of Strasburg; his brother Carl Hollifield (Maria) of New Market; his sisters Doreen Moore (Robert), and Deanna Kerby (Todd), both of Warrenton; brother-in-law Jean Dassonville (Nancy); as well as two generations of nieces and nephews.

Derry grew up in Fairfax, and at the age of 20, had recently dropped out of college, when he met his would-be wife, Chantal, with whom he’d spend the next 47 years. She was 22 with three daughters, and he always treated them as if he’d fathered them himself. He was kind, calm, and easy-going. He drove those girls to sports practice, to Skateland, to friends’ houses, etc. He built them a tree house, a playhouse, taught them to drive, walked them down the aisle… and was always, ALWAYS, there for them through every challenge. A girl could not ask for a better “bonus” dad!
Derry had a long and ever-increasingly responsible career with Fairfax County. While much of his retirement was spent caring for elderly French people, he never complained. By every measure, he was a good man.

Derry and Chantal traveled to France, Florida, the Outer Banks, and New Orleans. He enjoyed wine, good food, boating, card games, and road trips. A lifelong Redskins fan, Derry loved sports of all kinds, including football, college basketball, horse racing, NASCAR, and the affiliated fantasy leagues. And he excelled at them.
Derry also had a great love of music. As a younger man, he would spend hours taping music from vinyl albums and live radio to 8-track tapes. He taught his daughters to sing along to “Country Roads” by John Denver, “Take it Easy” by the Eagles, etc. He’d play his acoustic guitar and sing the hits of the day. (He could also play the accordion!)
There are no adequate words to capture his personality, kindness, fun spirit, or dependability. He did not seek the spotlight, but he was a role model, nonetheless.
Derry would not want attention paid to him. He’d rather see folks care for each other, their pets, and animals in general. He loved to watch Dr. Pol, and multiple other animal and zoo shows.

The best way to honor Derry would be to make a donation to your favorite animal-focused charity, and to raise a glass of rosé as you remember him.

No funeral service is planned at this time.
To order memorial trees or send flowers to the family in memory of Leonard Derrill Hollifield II, please visit our flower store.

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