Under the name Tony Dolan he had been, for a time, a conservative folk-singer who put out the album "Cry, The Beloved Country" and appeared on The Merv Griffin Show.

[2][3] He won the 1978 Pulitzer Prize for Local Investigative Specialized Reporting[1] for a series of articles on municipal corruption published in The Stamford Advocate.

During the presidency of President George W. Bush, Dolan served as Senior Advisor in the office of Secretary of State (December 2000 to July 2001) and Special Advisor in the Office of the Secretary of Defense (August 2001 to December 2007).

As Reagan's speechwriter, he wrote the speeches "Ash Heap of History" (1982) and "Evil Empire" (1983).

[4][5] His late brother Terry Dolan was co-founder and chairman of the National Conservative Political Action Committee (NCPAC).