He was acquainted with other activists such as Eugene Debs, Upton Sinclair, Jack London, and Fanny Bixby Spencer and spent considerable energy agitating for socialist causes.

By 1912, he along with members of the Los Gatos Baptist Church, decided to cancel all "ritualistic ceremonies" and make baptism optional.

[4] In 1898, he was appointed Superintendent of State Missions for Northern and Central California and gave sermons in various churches on the West Coast.

In 1901 he left the pastorate of the Baptist church in Palo Alto, California to engage in independent work in San Francisco.

[9][10] In 1906, Whitaker was accused of slander for charging Oakland City and Alameda County officials with corruption.