Major Cunningham is a native of Vermont.  He enlisted in the Marine Corps in October 2002 and attended recruit training at MCRD Parris Island, SC.  After completing MOS school, Lance Corporal Cunningham became a Dynamic Component / Tiltrotor Mechanic at MALS-29 on MCAS New River, NC.   He was meritoriously promoted to Corporal in 2004 and became a Collateral Duty Inspector (CDI).  In 2005 he was promoted to Sergeant and attached to HMM-162 (REIN) with the 26th MEU (SOC), in support of Operation Enduring Freedom / Iraqi Freedom, operating in Jordan and throughout the Persian Gulf.  While with the MEU he became the NCOIC in the Aircraft Intermediate Maintenance Department (AIMD) aboard the USS KEARSARGE (LHD-3).  

Upon return from deployment, Sergeant Cunningham was accepted into the Marine Enlisted Commissioning and Education Program (MECEP) and proceeded to The Citadel in Charleston, SC, where he was promoted to Staff Sergeant.  He graduated Magna Cum Laude with a Bachelor’s of Science in Business Administration and was commissioned as a Second Lieutenant in August 2009.  He proceeded to The Basic School in Quantico, VA and then attended Russian Language School in Fredericksburg, VA due to the backlog of Student Naval Aviators at that time in flight school. 

First Lieutenant Cunningham checked into MATSG-21 in Pensacola, FL in December 2010 for flight training and was assigned to VT-6, VT-2, and HT-8.  In June 2012, he checked into MATSG-22 in Corpus Christi, TX and was assigned to VT-35 where he was designated a Naval Aviator in December 2012.  

Captain Cunningham completed MV-22B training with VMMT-204 and was assigned to VMM-266 at MCAS New River, NC.  While with VMM-266, he deployed twice in support of SPMAGTF-CR-AF, conducting operations throughout Europe, in Morocco, and Djibouti where he served in the Operations Department, as the Administration Officer, and later as the Logistics Officer.

In November, 2017, Captain Cunningham was assigned to VMMT-204 as a Fleet Replacement Squadron Instructor (FRSI).  While at VMMT-204, he served as the Flight Equipment OIC and the Navigation Officer.  He was promoted to Major in November, 2019 and served as the Foreign Military Sales Officer, where he facilitated MV-22B flight training for the Japanese Ground Self Defense Force (JGSDF) and liaised with the Joint Program Office (PMA-275) as they prepared to establish the first Japanese Osprey squadron.  Major Cunningham later served as the Assistant Operations Officer and is currently the Executive Officer of VMMT-204.