Winter, a 1984 graduate of the University of Notre Dame with a Bachelor of Science in mechanical engineering, received his commission through the Naval Reserve Officer Training Corps and was designated a naval flight officer in 1985.
At sea, Winter flew the A-6E Intruder with Attack Squadrons 42, 85 and 34 aboard aircraft carriers USS Saratoga (CV 60), USS America (CV 66), USS Dwight D. Eisenhower (CVN 69) and USS George Washington (CVN 73).
Winter was selected as an aerospace engineering duty officer in 1995. His NAVAIR shore assignments include assistant deputy program manager for the Joint Standoff Weapon System; executive assistant to the Joint Strike Fighter (JSF) program director; team lead for JSF Integrated Flight and Propulsion Control; deputy program manager for the Tactical Tomahawk All-Up-Round (AUR) development program; PEO for Tactical Air chief of staff; and Precision Strike Weapons (PMA-201) program manager.
He most recently served as the commander of the Naval Air Warfare Center Weapons Division, China Lake/Point Mugu, Calif. and as the assistant commander for Test and Evaluation, Naval Air Systems Command.
Winter holds a master's degree in computer science from the Naval Postgraduate School and another a in national resource strategy from National Defense University’s Industrial College of the Armed Forces; and a Level III Program Management certification from the Defense System Management College.
His personal awards include the Legion of Merit, Defense Meritorious Service Medal (2), Navy Meritorious Service Medal (2); Navy Commendation Medal (4), Joint Service Achievement Medal (2), Navy Achievement Medal; Air Force Acquisition Excellence Award, Southwest Asia Service Medal; Kuwait Liberation Medal; and various unit and sea service awards.