Colonel Cunningham is from Lancaster, Ohio and entered the Marine Corps in July 1992. After graduating from 3rd Battalion, Parris Island Recruit Depot and Marine Corps Combat Training, he served as an admin clerk with Military Police Company C, Dayton, Ohio until 1996 when he was commissioned as a 2ndLt through the PLC program. His first officer assignment was Analysis and Plans Officer at 3D Marine Air Wing, El Toro MCAS, California and deployed with the 13th Marine Expeditionary Unit (MEU) as the Composite Squadron S-2, where he supported Operation Southern Watch in Kuwait.
In 2000 he moved to Miami, Florida where he served as the Colombia Branch Chief, Joint Intelligence Center, US Southern Command. He led a team of 40 analysts conducting intelligence in support of counterterrorism operations in Colombia and also provided intelligence assessments that influenced Congress to change US policy on Colombia. In 2003, he served as the Senior Intelligence Analyst in Bogota, Colombia for a US hostage situation.
Later in 2003, he left active duty to take an assignment with the National Air and Space Intelligence Center (NASIC) to conduct intelligence analysis on adversary air, space, and missile systems.
At the same time, he served in the Marine Corps Reserves as the Senior Intelligence Analysts for European Command’s Regional Analysis Branch and, later in 2007, as the Branch Chief. In 2009, he transferred to serve as IMA to the Plans Officer, MARFORPAC, G2, Hawaii, where he supported several exercises and real world crises. He mobilized in February 2011 to serve as the Senior Intelligence Analyst for a Joint Task Force in Afghanistan. He provided intelligence for over 110 combat operations, which resulted in 300 detainees. In 2012, he was assigned as the Commander for Bravo Company, Intelligence Support Battalion (ISB) in Aurora, Colorado. He served in this position for three years, until he became the Commanding Officer of ISB in 2015 where he lead over 500 Marines and Sailors from four geographically dispersed companies stationed across 19 sites throughout the country. After battalion command, he joined 3D Civil Affairs Group as a detachment commander until he was promoted to Colonel in May 2018 when he was activated for 5 months to serve as the Chief of Staff for Force Headquarters Group.
Currently, in his civilian job, he serves as the Principal Intelligence Analyst for Long-Range Forecasting and provides the Air Force Leadership with in-depth analysis of future enemy warfighting capabilities and operational concepts to help drive U.S. future weapons development.