He pursued a career in retail before moving into business ventures in cattle and iron manufacturing.

He received his education at a district school and attended Bryant and Chase Business College in Chicago, Illinois.

He then invested in a herd of range cattle in Wyoming and an iron manufacturing business in Rockford, Illinois.

[1] On March 22, 1910, two members of the Los Angeles City Council, John D. Works and Richmond Plant, resigned.

Works left to pursue a seat in the U.S. Senate, while Plant resigned amid an investigation.

Among them were Chief of Police Charles E. Sebastian and future councilmembers Robert M. Allan and Ralph Luther Criswell.

[12] In September 1916, Whiffen alleged that he had been offered the position of mayor for $2,500 to succeed Sebastian, who had resigned amid scandal.