In 1934, he acquired Sapelo Island on the Atlantic coast of Georgia[4] and, following the death of Tillinghast L'Hommedieu Huston in 1938, the Butler Island Plantation[5] Reynolds was appointed treasurer of the Democratic National Committee in early 1941 before being elected mayor of Winston-Salem, North Carolina, a few months later.
[6][7] He took a leave of absence from his mayoral duties and resigned his treasurer post in 1942 when he began military service as a lieutenant at the Naval Combat Intelligence School in Quonset Point, Rhode Island.
[8][9] As a businessman, he did not work at R. J. Reynolds Tobacco Company except as a young teenager.
He was also a yachtsman (having the 125 ton ketch Aries built for him in 1952[10]), pilot, aviator, and philanthropist.
[15] Reynolds was diagnosed with emphysema in 1960 and died four years later in Switzerland.