Most recently, Bailey was political director for the ACLU of Florida — the first ACLU affiliate political director in the nation — leading the organization’s public policy and advocacy portfolio, including direct lobbying, organizing, and electoral and issue campaign initiatives. Prior to the ACLU, Bailey served in a variety of roles — as vice president of government affairs at the Outdoor Industry Association, as counsel at Smith Dawson & Andrews, and as special counsel at the Hamilton Fish Institute on School and Community Violence.

He is a long time volunteer and leader with Election Protection — the non-partisan voter protection and election observer program — extending back to 2004 and including service in various roles such as a national call center volunteer, Florida field volunteer, Florida regional command center leader, and Florida command center voting rights expert. Bailey’s legislative experience includes professional staff positions with the state legislatures of Oregon, Hawaii, and Alaska; and with former U.S. Senator Frank Murkowski (AK) in Washington, D.C. In addition, he is a published author on school safety, youth violence, and civil liberties concerns. Bailey is a graduate of the University of Oregon in political science and holds a J.D. from the University of Oregon School of Law, where he also served on the Journal of Environmental Law & Litigation. He is admitted to the Oregon State Bar and a member of the American Bar Association.