Major Winters graduated from the University of San Diego in 2009 and commissioned via the Officer Candidate Course (OCC) in 2010. After commissioning, Major Winters completed the Basic Officer Course (2010) and Infantry Officer Course (2011) at The Basic School before reporting to his first unit.
From 2011-2014, Major Winters served as a Rifle Platoon Commander, Security (Recon) Platoon Commander, and Company Executive Officer at 3d Battalion, 5th Marines (V35). From 2012-2013, the unit deployed as the battalion landing team for the 15th Marine Expeditionary Unit (MEU). During his three years with V35, Major Winters served with Companies L, K, and H&S.
In 2014, Major Winters graduated from the Basic Reconnaissance Course and shortly after reported to 3d Reconnaissance Battalion, 3d Marine Division. From 2014-2018, Major Winters deployed on three separate occasions with the 31st MEU, twice as a Maritime Raid Force Commander and once as a Force Reconnaissance Platoon Commander. While completing Expeditionary Warfare Blended Seminar Program, he served as a Force Reconnaissance Detachment Officer-In-Charge for numerous short deployments in support of III Marine Expeditionary Force and Theater Special Operations Command.
From 2018-2021, Major Winters served as a Force Reconnaissance Company Commander, Battalion Operations Officer, and Battalion Executive Officer with 2d Reconnaissance Battalion, 2d Marine Division. During this time, Major Winters also deployed with II Marine Expeditionary Force to Norway for Exercise Trident Juncture 2018, and completed Command and Staff Course Distance Education Program. In 2021, Major Winters reported to Expeditionary Warfare School to serve on the faculty.
Major Winters’s has completed a variety of high-risk military training and supervisory courses. His experiences range from supporting ground operations and maneuver to conducting specialized integration with special operations forces. Most of his deployments have focused heavily on building close relationships with allies and partners.