Sergeant Major Fliegel enlisted into the Marine Corps in December 1986 from Northfield Minnesota, where he grew up. He attended recruit training from July to September 1987 with Third Recruit Training Battalion at Marine Corps Recruit Depot San Diego California. Upon graduation, Private Fliegel reported to Marine Corps Engineer School at Court House Bay on Camp Lejeune North Carolina and obtained the MOS of 1371, Basic Combat Engineer.

Private Fliegel was assigned to Bravo Company, Ninth Engineer Support Battalion (9th ESB), Third Marine Division on Okinawa Japan from December 1987 to December 1988.

January 1989, Lance Corporal Fliegel checked in to Second Combat Engineer Battalion (2nd CEB) at Camp Lejeune North Carolina and was assigned to Bravo Company for duty. He held the billets of team leader, squad leader, and platoon guide after being meritoriously promoted to Sergeant in August 1992. While assigned to 2nd CEB he supported contingency operations and operation Promote Liberty in the republic of Panama, operation Desert Shield and Desert Storm in South West Asia, and completed a Marine Expeditionary Unit (MEU) deployment.

From May 1993 to May 1994, Sergeant Fliegel preformed the duties of mine field maintenance at Guantanamo Bay Cuba.

In September 1994, He completed Drill Instructors school class 4-94 and was assigned to Second Recruit Training Battalion, Marine Corps Recruit Depot, San Diego California. Sergeant Fliegel completed five cycles as a Drill Instructor and two as a Senior Drill Instructor with Hotel Company over the next Two years.

From October 1996 to January 2004 he was stationed at First Combat Engineer Battalion (1st CEB), Camp Pendleton California. Sergeant Fliegel was a Platoon Sergeant with Charlie Company until his promotion to Staff Sergeant. During November 1997, he was transferred to Alpha Company as a Platoon Guide in support of a Wes-Pac Marine Expeditionary Unit (MEU) deployment. From December 1999 to January 2004 Gunnery Sergeant Fliegel was the Company Gunnery Sergeant for Alpha Company and deployed for Operation Iraqi Freedom (OIF) with 1st Marine Regiment as the Regimental Engineer Chief.

January 2004, he was promoted to First Sergeant and reported to Second Battalion, Seventh Marines at Twenty-nine Palms California. He served as Company First Sergeant for Fox Company and later Weapons Company while there he completed 3 more OIF deployments. In November 2007, he was selected to Sergeant Major and received orders to Third Marine Aircraft Wing.

He served as Marine Fighter Attack Squadron 323 Sergeant Major from January 2008 to August 2010 and completed one CVN Wes-Pac deployment with Carrier Air Wine Nine.

Sergeant Major Fliegel assumed the duties of Sergeant Major for Marine Fighter Attack Training Squadron 101 during September 2010 until his transfer to Headquarters Battalion during May of 2012.

His personal decorations include the Navy Commendation Medal with gold star, Navy and Marine Corps Achievement Medal with combat distinguishing device and gold star, Army Achievement Medal, and Combat Action Ribbon with gold star.