Colonel Winthrop graduated from the Ohio State University and was commissioned in 1995 as a Combat Engineer Officer. Upon completion of entry-level training, he served in the 2d Marine Division as a Platoon Commander with the 2d Combat Engineer Battalion, 2d Light Armored Reconnaissance Battalion and Battalion Landing Team 2/2, 22nd Marine Expeditionary Unit. While assigned to the 22nd MEU (SOC), he participated in the embassy reinforcement in Tirana, Albania in 1998.
From 1999 to 2001, he served as the Inspector-Instructor, B Company, 4th Combat Engineer Battalion, 4th Marine Division in Roanoke, Virginia. While in this assignment, he deployed to Macedonia in support of Kosovo Operations. From August 2001 to May 2002, he attended the Amphibious Warfare School (AWS) in Quantico, Virginia. Upon graduation from AWS, he was reassigned to the Marine Corps Officers Candidate School.
From September 2002 to September 2003, he served as the Commanding Officer of B Company, 7th Engineer Support Battalion during Operation Iraqi Freedom. During OIF I, B Company executed the assault breach of the Iraqi/Kuwaiti obstacle belt in direct support of Task Force Tarawa. During OIF II, he served as the Operations Officer for 7th Engineer Support Battalion and later the Operations Officer of Combat Service Support Battalion-1 in direct support of Regimental Combat Team-1 during Fallujah Operations. In May 2005, he was reassigned to Combat Logistics Regiment-15 as the Regimental Operations Officer. He deployed to Iraq for a third time with CLR-15 in support of I MEF during OIF 05-07. Upon completion of this tour, he attended the Marine Corps Command and Staff College.
He was reassigned to the Marine Air Ground Task Force (MAGTF) Staff Training Program (MSTP) in Quantico, Virginia as an instructor in the MAGTF Branch and later the Branch Head of the Exercise Design Division. While serving at MSTP, he deployed to Afghanistan with Special Purpose MAGTF-Afghanistan as an Operational Planner with 3d Marines. Upon redeployment from Afghanistan, he attended the School of Advanced Warfighting (SAW).
Upon graduation from SAW in 2010, he reported to I MEF G-5 as a Regional Plans Officer. In October 2010 through July 2011, he deployed to the Kingdom of Bahrain with MARCENT (Forward). Upon redeployment, he served as the I MEF G-5 Chief of Plans. Later he served as the Deputy G-3, 1st Marine Division before assuming command of the 1st Combat Engineer Battalion.
He commanded the 1st Combat Engineer Battalion from 2012 to 2014. He deployed with the Battalion to the Helmand Province, Afghanistan in support of Operation Enduring Freedom from October 2013 until April 2014. Upon relinquishing command, he attended the National War College in Washington, DC where he earned a Master of Science in National Security Strategy in June 2015.
Following Top Level School, he was reassigned to the Office of the Secretary of Defense as the Deputy Director in the Rapid Reaction Technology Office and later as the Military Assistant to the Deputy Assistant Secretary of Defense for Emerging Capability and Prototyping. After his tour at OSD, from 2018-2021 he served at Headquarters, Marine Corps as the Director of Current Operations at Capability Development Directorate, Deputy Commandant, Capability Development and Integration and later, the Futures Branch Head, Logistics Plans, Deputy Commandant, Installations and Logistics.
His personal awards include the Defense Superior Service Medal, the Legion of Merit, the Bronze Star Medal with gold star in lieu of second award, Meritorious Service Medal with two gold stars in lieu of third award, Navy and Marine Corps Commendation Medal with gold star, Navy and Marine Corps Achievement Medal, Combat Action Ribbon, and Marine Corps Engineer Association’s Combat Engineer Officer of the Year Award for 2004.