Tom Bailey, District 2

About Councilmember Bailey

Tom retired from the United States Air Force as a Colonel after a 26-year career as an intelligence officer, educator, and leader. Since his retirement in 2012, Tom has devoted himself to charitable endeavors and civic service, while continuing to manage a variety of real estate investments.

Born in LaJunta, Tom is the oldest of four children of an Air Force non-commissioned officer and Vietnam veteran. He graduated from the United States Air Force Academy in 1986, and his service included two overseas tours in Europe and two tours at the Pentagon.

Tom earned a Master of Arts in Political Science from the Ohio State University in 1994, and taught political science and developed leaders at the Air Force Academy from 1994-1997. He also holds a master’s degree from the Naval War College, where he served as a member of the faculty from 2006-2009. He continues to teach military strategy through their College of Distance Education

Since returning to Colorado Springs in 2012, Tom has volunteered with Parents Challenge, the Career Building Academy, and the Center for Nonprofit Excellence’s Executive Service Corps. He serves on the boards of two nonprofit organizations and volunteers at St Peter Catholic Church in Monument. From 2018 to 2025, Tom was a member of the El Paso County Planning Commission and was selected as its chairman in 2023.

Tom has been married to the former Julie Phillips of Laguna Beach, California for over 35 years. They have two children: Colleen is a 2013 graduate of the University of Notre Dame and lives in South Bend, IN, with her husband and four children; and Danny is a 2016 graduate of the University of Colorado in Boulder and resides in Denver.