Whitehead was president of the Simplex Automobile Company but retired in 1910 to devote himself to bridge.
[1] Whitehead was one of the members of the Bridge Headquarters, a group of experts who developed a bidding system named the Official System.
Sidney Lenz (another Bridge Headquarters member) deployed this system against Ely Culbertson in the so-called "Bridge Battle of the Century" of 1931.
(Whitehead had helped Culbertson during Culberton's early days of poverty).
[1] He wrote a daily bridge column, "Sound Auction Bridge", which appeared in the New York Evening Journal.