Originally from San Antonio, Texas, Commander Winn graduated from Morehouse College in 2003 where he received a Bachelor of Arts in Economics and was commissioned through NROTC. He also holds a Master of Science degree in Systems Engineering and Analysis from the Naval Post Graduate School.
At Sea, CDR Winn has served as Auxiliaries Officer in USS SIMPSON (FFG 56), Training Officer in USS CLEVELAND (LPD 7), First Lieutenant in USS CARTER HALL (LSD 50), AND CHIEF Operations Officer at AMPHIBIOUS SQUADRON FOUR.
Ashore, CDR Winn served as Placement Officer and Assistant Director for Director, Surface Officer Distribution at PERS-41, as well as a Manpower Action Officer and Deputy Executive Assistant for Director, Expeditionary Warfare Systems (OPNAV N95).
His personal awards include the Navy commendation Medal (5 awards) and various unit and service awards.