While working on his master's degree in Madison, Whitburn became involved in Republican Party politics on the 1966 re-election campaign of Governor Warren P. Knowles.
After earning his master's degree, Whitburn moved to Washington, D.C., and worked as an aide to John Chafee, who was then United States Secretary of the Navy in the Nixon administration.
In 1972, Chafee resigned to seek election to the United States Senate from Rhode Island, and hired Whitburn as his campaign director.
[4] In 1989, Thompson named Whitburn to the cabinet position of Secretary of the Wisconsin Department of Industry, Labor and Human Relations.
In the Fall of 1994, Whitburn agreed to bring his experience to a new state as Secretary of Health and Human Services of Massachusetts, under Republican governor Bill Weld.