The son of an English silversmith, at the age of sixteen Whitaker began working in the design department of W.J. Feeley and Company, a Providence manufacturer of religious articles in metal. He studied life drawing in evening classes at the Rhode Island School of Design for four years. In 1921 he was working as a designer for Tiffany in New York, commuting to be with his family who remained in Providence; his work with Tiffany and the Gorham company continued for some years.
Whitaker combined an active and successful business career with an equally active career as a painter in watercolor. By 1941, he had purchased the Foley and Dugan Company of Providence as well as the G. H. Seffert Company in New York, two firms which specialized in the manufacture of ecclesiatical objects.
In 1912 the artist married Marie Tiedge. The couple separated in 1940, at which time Whitaker moved to New York. Following a divorce in 1950, he married fellow-watercolorist Eileen Monaghan. At this time he turned his businesses over to his sons, moved to Norwalk, Connecticut, and devoted himself fully to his painting, writing on watercolor techniques, and to expanding his already active involvement in numerous artists professional associations.
He became president of the American Water Color Society in 1949, a position he retained to 1957. The Academy elected him to his first three-year term on the Council in 1952; he was a vice president of the Academy, 1956-57, and was returned to the Council in 1961 for another three-year term.
The Whitakers moved to La Jolla, California, in 1965.