Stewart, Councilman, Town of Chesapeake Beach, is a past member of the Board of Directors of the Maryland Municipal League and served as their 2007-2008 President. He has served as MML First Vice President, District 4 Vice President (Southern Maryland), and twice served as President of the Southern Maryland Municipal Association. He has served as Chairman (2005 & 2006) of the MML Convention Planning Committee and serves on the Hometown Emergency Preparedness Committee. He serves as Chairman of the LGIT Risk Management Committee and a member of LGIT Claims Committee. He has served as the Vice-Chairman of the Calvert County State Democratic Central Committee and served on the State Rules Committee. Stewart is a graduate and Fellow of the Academy for Excellence in Local Governance, University of Maryland. He has a Bachelor of Arts from the University of Maryland, Division of Behavioral and Social Sciences, Criminology, and a Master of Science in Management from the Johns Hopkins University, School of Professional Studies in Business and Education. He is a member of Leadership Maryland Class 2006. Stewart is also a graduate of the Police Executive Leadership Program, Johns Hopkins University and successfully completed the University of Delaware, Criminal Justice Leadership Institute. He is a Detective Sergeant and Commander of the Barrack Criminal Investigative Section with the Department of Maryland State Police and a Crisis Negotiator (Team Leader) on their Hostage Recovery Team. He is a former Police Officer of the Metropolitan Police Department, Washington, D.C. and former Deputy United States Marshal.