Major Fleming graduated from Rutgers University of New Jersey with a Bachelor of Arts degree and was commissioned a Second Lieutenant in May 2002. Upon completion of The Basic School, he reported to Flight School in Pensacola, Florida and was designated a Naval Aviator in November 2004.
After completing the AH-1W Replacement Air Crew syllabus at HMT-303, he reported to the HMLA-169 Vipers in May 2005 where he served as a Schedule Officer, Flight Officer, Pilot Training Officer, and Aviation Safety Officer. From March 2006 through April 2008, Captain Fleming deployed twice to Al Anbar Province in support of Operation Iraqi Freedom.
In October 2008, Captain Fleming attended the Weapons and Tactics Instructor Course. In March 2009, he deployed to Helmand Province, Afghanistan in support of Operation Enduring Freedom as the Future Operations and Plans Officer. Captain Fleming was selected to serve as the Escort Flight Leader and lead HMLA planner for Operation Khanjar, the main effort for Regional Command South for the summer of 2009 and the largest offensive heliborne operation since the Vietnam War.
Upon redeploying, Captain Fleming served as the Director of Safety and Standardization for HMLA-169. In June 2010, he reported to Marine Aviation Weapons and Tactics Squadron One to assume the Aviation Safety Officer billet and serve as an AH-1 Instructor Pilot. While at MAWTS-1, Captain Fleming was selected to participate in an Israeli pilot exchange, flying the AH-1S in Israel during the Israeli Air Force Flight Leader course. In 2013, he was selected to attend the French Advanced Command and Staff College in Paris, France. After language training at the Defense Language Institute in Monterey, California, Major Fleming attended the Ecole de Guerre (“School of War”), serving as the President of the 96 International Officers from January 2014 to June 2015. During this time he also completed a Master’s Degree from the School of Advanced Studies in the Social Sciences. He subsequently earned the military occupational specialty of Foreign Area Officer, Europe.
In August 2015, Major Fleming joined the HMLA-167 Warriors to serve as the Assistant Operations Officer during the Unit Deployment Program to Okinawa, Japan. Upon redeploying in May 2016, he assumed the Operations Officer billet. In April 2017, he assumed his current billet as the Executive Officer.
Major Fleming’s personal awards include the Air Medal with combat “V” device and Strike/Flight Numeral "13”, and the Navy and Marine Corps Commendation Medal with two gold stars.