Gunnery Sergeant Milstead enlisted in the Marine Corps on June 19, 2001 and completed recruit training at MCRD San Diego on September 14, 2001. Following recruit training, Private Milstead attend infantry training at Infantry Training Battalion, School of Infantry-West, Camp Pendleton, California. Upon graduation in December of 2001, he reported to Security Force School in Chesapeake, Virginia.
In March of 2002, Private First Class Milstead reported to Interim Security Force Company, Bahrain where he served as a Team Leader and Corporal of the Guard and operator in the Combat Operation Center while in support of OPERATION SOUTHERN WATCH and OPERATION DETERMINED RESPONSE. He was promoted to the rank of Lance Corporal in September of 2002. In March of 2003, Lance Corporal Milstead reported to Security Force Company Patuxent River, Maryland. He served as a Team Leader and Corporal of the Guard and was promoted to the rank of Corporal in February of 2004.
In March of 2004, Corporal Milstead was assigned to 3d Battalion, 6th Marines where he served as a Team Leader and Squad Leader for 1st platoon, India Company. He deployed in support of OPERATION ENDURING FREEDOM from May 2004 until December 2004. After redeploying, he served as the Platoon Sergeant until his assignment to the 6th Marines Regimental Training Center in early 2005. Corporal Milstead served as a platform instructor for the Enhanced Marksmanship Program and the Marksmanship Coaches Course and was promoted to the rank of Sergeant in September of 2005.
Sergeant Milstead reported to Combat Instructor School in September of 2005. Upon graduation, he reported to Charlie Company, Infantry Training Battalion where he served as the company machinegun instructor. In August of 2006, Sergeant Milstead was assigned to the Machinegun Section, Weapons Instructor Group, Infantry Training Battalion and served as a platform instructor until his rotation in December of 2008.
In January 2009, Sergeant Milstead reported to 3d Battalion, 9th Marines where he served as the Machinegun Section Leader for Weapons Platoon, India Company. He deployed in support of OPERATION IRAQI FREEDOM from July 2009 until October 2009. He was promoted to the rank of Staff Sergeant in December of 2009. Staff Sergeant Milstead volunteered for an Individual Augment billet in Liberia, Africa in support of OPERATION ONWARD LIBERTY. From January 2010 until January 2011, he served as a mentor to the staff of the Armed Forces of Liberia. After redeploying, Staff Sergeant Milstead was reassigned temporarily as the Chief Instructor at Combined Arms Staff Trainer, Camp Lejeune. In October 2011, Staff Sergeant Milstead returned to 3d Battalion, 9th Marines and was assigned to the battalion S-3 where he served as the Training Chief. Staff Sergeant Milstead deployed from October 2012 until May 2013 serving as the Battalion Watch Officer in support of OPERATION ENDURING FREEDOM.
In August 2013, Staff Sergeant Milstead received orders to G-3, 4th Marine Division in New Orleans, Louisiana, and served as the Division Formal Schools Coordinator and Division Training Chief.
In March 2016, Staff Sergeant Milstead received orders to School of Infantry-East and was assigned to Kilo Company, Marine Combat Training Battalion where he served as a Squad Instructor, Platoon Commander, Company Gunnery Sergeant, Company First Sergeant, and Company Executive Officer. Gunnery Sergeant Milstead was promoted to his current rank on July 1, 2016. In November of 2016, Gunnery Sergeant Milstead was reassigned to Combat Instructor School where he currently serves as the Chief Instructor.
Gunnery Sergeant Milstead’s personal decorations include the Navy and Marine Corps Commendation Medal, Joint Service Achievement Medal, Navy and Marine Corps Achievement Medal (4th award) and the Combat Action Ribbon.