[2] He worked for Republican candidates for Governor, Senate and president including: President Gerald Ford; senators Edward Brooke, Kit Bond, John Danforth, Charles Percy, Richard Schweiker, John Chafee, Richard Lugar, Robert Stafford, Howard Baker; governors Thomas Kean, William Milliken, Jim Rhodes, Otis R. Bowen, James R. Thompson, Lamar Alexander, Richard Snelling, William T. Cahill, Richard Thornburgh, Jim Rhodes, Robert Ray, Al Quie, Pete DuPont.

[citation needed] He started The Hotline, a daily political newsletter delivered by fax, in 1987.

[3] Each issue, faxed in the late morning, included a roundup of political jokes from the previous night's talk-show monologues.

He founded Freedom's Answer, a non-partisan voter turnout effort, with former Clinton Press Secretary Mike McCurry.

[5] In January 2008, Bailey and fellow Unity08 co-founder Gerald Rafshoon left that organization to launch a national effort to draft New York City Mayor Michael Bloomberg to run for president as an independent candidate.