When the American Civil War began, he was elected as first captain of the Mountain Rangers of Winchester, which became Company D of the 33rd Virginia Infantry Regiment.

Holliday won the election for Governor of Virginia in 1877 as a Conservative Democrat unopposed.

Holliday began his term by breaking the established tradition of small inauguration ceremonies for Virginia governors.

His ceremony included parades, bands, cannons, and an inaugural speech to 10,000 people.

He died at his home in Winchester, Virginia, on May 29, 1899,[2] and was buried in Mount Hebron Cemetery.