He started The Hotline, a daily political newsletter delivered by fax, in 1987. It began partly as an experiment in bipartisanship.[3] Each issue, faxed in the late morning, included a roundup of political jokes from the previous night's talk-show monologues. He sold it to the National Journal in 1996.[4]
After he left day-to-day operations, Bailey was involved in numerous philanthropic activities. Most recently, he was one of the four co-founders of the political reform movement Unity08. He was seeking to start a new centrist party for the 2008 presidential election to try to unite the country. He appeared on The Colbert Report to promote his cause. He founded Freedom's Answer, a non-partisan voter turnout effort, with former Clinton Press Secretary Mike McCurry. He also served on the board of directors of the Fletcher School at Tufts University.
In 1994, Bailey joined Jeffrey Pollack in a venture to start a daily briefing for the sports world called the Sports Business Daily. This venture originally occupied three rooms in the same building as The Hotline, and was sold in 1996.[5]
Bailey sat on the Council on American Politics, which brings leaders from the political and communications arenas together to address issues facing the growth and enrichment of GW's Graduate School of Political Management.[7]
"What I've Learned: Doug Bailey" "A political guru on the problem with campaign consultants, why people are getting fed up with both parties, and why big changes are on the way" by Ken Adelman, The Washingtonian, November 1, 2006.