Major Flagg joined the Hanover County Sheriff’s Office in July of 1995.  As a deputy, he worked on all of the patrol shifts with the majority of his service being on Evening Shift.  He served as a field training officer, Crash Team member, and became an instructor of police tactics and firearms under the Department of Criminal Justice Services.  

In 2002, Major Flagg was promoted to sergeant.  As a sergeant and as he was appointed to Lieutenant and later Captain, Major Flagg worked in the Patrol and Administrative Divisions as well as in the office of Professional Standards and Risk Management.  In these assignments, he has contributed in the development of countless programs, to include the development of training and policy. As a lieutenant, he led the effort to establish an independent training academy certified by the Virginia Department of Criminal Justice Services and served as its first Academy Director.  He has supervised numerous research programs and worked on the deployment of new technologies such as our body worn camera systems and other forms of equipment and processes, to better enable our officers to serve our community.   

In conjunction with his other duties and assignments, Major Flagg served 16 years on our High Risk Entry Team in various capacities to include team leader.  He has received numerous awards to include Dedication to Duty, Excellent Service, Medal of Valor and the agency’s Purple Heart.   

Major Flagg graduated summa cum laude with a Bachelor of Science, Criminal Justice, from Virginia Commonwealth University.  He has attended Virginia Tech’s Institute for Leadership in Changing Times, the University of Richmond’s Police Executive Leadership Seminar, as well as courses offered through the Southern Police Institute at the University of Louisville and the Command Institute for Law Enforcement Executives (FBINAA).  In 2021, Major Flagg successfully completed the Law Enforcement Executive Program through the University of North Carolina.    

Major Flagg is a life-long citizen of Hanover County.  He met his wife at and graduated from Patrick Henry High School.  He and his wife reside in the Beaverdam district of Hanover County where they have worked together to raise their three children.      

Since February of 2020, Major Flagg has been responsible for the Investigative Division.