Colonel Winters was commissioned at the U.S. Naval Academy on May 22, 1998. 2ndLt Winters completed the Air Defense Control Officer Course and reported to Marine Air Control Squadron Seven (MACS-7), MCAS Yuma, for duty as a Platoon Commander in the Tactical Air Operations Center (TAOC). While in Yuma, 2ndLt Winters attended the Strike Fighter Tactics Instructor Course (TOPGUN) and earned his Senior Air Director designation. In 2002, 1stLt Winters was selected to establish and command the new MACS-1 Early Warning and Control (EW/C) Detachment at MCAS Miramar. While in command, Captain Winters graduated from the Weapons and Tactics Instructor (WTI) Course and led his Detachment during Operation Iraqi Freedom (OIF)-1, controlling all combat airspace and intercepting 9 ballistic missiles. In 2004, Captain Winters relinquished command of the Detachment and transferred to Marine Air Control Group 38 (MACG-38), deploying to the USCENTCOM Combined Air Operations Center for duty as a Marine Liaison Officer.
In 2005, Captain Winters joined the initial cadre at the Marine Air Command and Control Squadron-Experimental (MACCS-X) Operational Development Team, serving as the Air Defense Division Head and Aviation C2 Transformation Lead. Captain Winters led developmental and operational tests of emergent aviation weapons systems, crafting the foundational doctrine and training for the future MACCS. In 2008, Captain Winters reported to Marine Tactical Air Command Squadron 38 (MTACS-38), establishing and assuming command of the Tactical Air Command Center (TACC) Company. Captain Winters led his Marines to Operation Iraqi Freedom 08 and performed tactical duties as a Senior Air Coordinator. Upon return from Iraq, Major Winters assumed duties as the MTACS-38 Operations Officer. Major Winters deployed to Camp Leatherneck Afghanistan, serving as the MTACS-38 (FWD) Operations Officer and Senior Air Coordinator. In 2011, Major Winters graduated with highest distinction from the U.S. Naval War College.
Upon graduation, Major Winters reported to Marine Aviation Weapons and Tactics Squadron One (MAWTS-1) for duty as the Command, Control and Communications (C3) and Spectrum Warfare Department Head, leading six Weapons and Tactics Instructor courses. In 2014, Major Winters reported to MACG-28 for duty as Assistant Operations Officer and Group Weapons and Tactics Instructor. From February 2015 to June 2017 LtCol Winters commanded Marine Air Support Squadron One, where his Marines ranked first in IIMEF during their FSMAO inspection and earned the 2nd MAW Command and Control Squadron of the Year award. In 2018, LtCol Winters graduated first in his class from the National War College and earned the Marine Corps Association’s Colonel Richard Christie Award for academic excellence. LtCol Winters then served on the Joint Staff as the J-3 Operations Directorate’s Russia Problem Set lead and Secretary of Defense Orders Book Briefer, earning the 2020 Joint Staff Officer of the Year award. In June 2020, Colonel Winters was merit reordered and promoted to his current rank, serving at HQMC as Deputy to the Director for Information Command, Control, Communications and Computers (IC4). Colonel Winters reported to MACG-38 in June 2021.
Colonel Winters’ personal awards include the Defense Meritorious Service Medal, Meritorious Service Medal, Joint Commendation Medal, Navy and Marine Corps Commendation Medal, Joint Achievement Medal, and Navy Achievement Medal. Colonel Winters performed over 12,000 combat crew hours in the MACCS. Colonel Winters earned a BS in Political Science from the U.S. Naval Academy, an MA in Business Administration (distinction) from National University, an MA in National Strategic Studies (highest distinction) from the U.S. Naval War College, an MS in National Security Strategy (highest distinction) from the National War College, and a Masters’ Certificate (distinction) as a Chief Information Officer from the National Defense University College of Information and Cyberspace. Colonel Winters is a Massachusetts Institute of Technology Seminar XXI National Security Fellow.