Mr. Flagg is from New Berlin, Wisconsin and enlisted in the Marine Corps Reserve in 1987. Mr. Flagg was a rifleman in Fox Company, 2d Battalion, 24th Marines, Milwaukee, Wisconsin from 1988 to 1990. Upon graduation from the University of Wisconsin, Whitewater, Mr. Flagg attended the Officer Candidates School (Honor Graduate), The Basic School and the Logistics Officer’s Course.
From 1991 to 1994, Mr. Flagg served as the Logistics Officer, 2d Maintenance Battalion, 2d Force Service Support Group, Camp Lejeune, North Carolina. Mr. Flagg was selected to serve as the Officer in Charge, Camp Mujuk, Pohang Korea from 1994 to 1995. Following his tour in Korea, Mr. Flagg attended the Amphibious Warfare School, Quantico Virginia from 1995 to 1996. Upon completion of Amphibious Warfare School, Mr. Flagg was assigned as the Logistics Officer, Marine Corps Security Forces Battalion, Norfolk, Virginia from 1996 to 1999. Mr. Flagg left active duty and rejoined the Marine Corps Reserve serving as the Assistant Operations Officer, 4th Supply Battalion, Newport News, Virginia from 1999 to 2000.
Mr. Flagg returned to active duty in Marine Corps Active Reserve in 2000 and was assigned as the Maintenance Detachment Officer in Charge at the Equipment Allowance Pool, Marine Air Ground Task Force Training Command, Twentynine Palms California from 2000 to 2005. During this tour, Mr. Flagg deployed to Operation Iraqi Freedom and was assigned as Logistics Officer to 1st Light Armored Reconnaissance Battalion, 1st Marine Division. Mr. Flagg returned to Twentynine Palms and served as a maneuver coyote and logistics trainer for the Tactical Training Exercise Control Group.
From 2005 to 2007, Mr. Flagg served as the Training Officer, Marine Forces Pacific, Honolulu, Hawaii. In 2007, Mr. Flagg was transferred to III Marine Expeditionary Force Headquarters, Okinawa, Japan and served as the Reserve Liaison Officer and Korea plans officer.
Mr. Flagg retired from Active Duty in January, 2011 and served as the Camp Director for Camps Courtney and McTureous until July, 2012 and then transferred to Camps Foster and Lester. Mr. Flagg received a Master of Business Administration Degree from the University of Phoenix in 2012.