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While attending law school at UNC, Cal Cunningham initially enlisted in the U.S. Naval Reserve and, after boot camp at Naval Station Great Lakes, achieved the rank of Petty Officer Third Class. But following the terrorist attacks on September 11, 2001, Cunningham transferred to the Army Reserve and, in 2002, received a commission as a First Lieutenant in the Judge Advocate General’s Corps.

XVIII Airborne Corps At Fort Bragg: 2005


First Lieutenant Cunningham served his first active duty tour with XVIII Airborne Corps and Fort Bragg as a Special Assistant United States Attorney in the Office of the Staff Judge Advocate. At Fort Bragg, he adjudicated hundreds of misdemeanor cases and numerous felony cases. 

 “A brilliant performance by one of the finest officers I have encountered in my 15 years of service. Displaying exceptional maturity and grace under pressure, 1LT Cunningham was the glue that held the office together during a time of significant transition. As a Special Assistant U.S. Attorney (SAUSA), Cal expertly prosecuted more felony cases than any other attorney in the office, procuring multiple indictments from the Grand Jury, and seeing many more cases through to sentencing.”  –Officer Evaluation, Major, 2005

Following his first tour, Cunningham came off active duty and served as an administrative and contract law officer at Fort Jackson. Cunningham was promoted to Captain in 2006 and graduated the Basic Airborne Course at Fort Benning.

Multi-National Corps-Iraq: 2007-2008

Captain Cunningham volunteered to deploy to Iraq for a year-long tour with the XVIII Airborne Corps in support of Operation Iraqi Freedom to Camp Victory where he served as the senior trial counsel for the Multi-National Corps-Iraq. 

Responsible for oversight of the Army’s largest court martial jurisdiction, including supervising and training dozens of lawyers and paralegals, Cunningham conducted and oversaw courts-martial, a role in which his work would lead to the first successfully prosecuted court-martial of a civilian contractor since the Vietnam War. 


Cunningham helped lead the development and implementation of the Multi-National Corps-Iraq process for referring cases for prosecution under the Military Extraterritorial Jurisdiction Act (MEJA), developing a new system for holding government contractors accountable by transferring cases from Iraq to the Department of Justice. This involved everything from investigating cases in the field, to courtroom hearings and trials.

 “Widely recognized throughout MNC-I and MNF-I as the resident legal expert on civilian misconduct […] CPT Cunningham took the initiative to train MNC-I trial counsel and attorneys from the Joint Contracting Command Iraq and the Army Materiel Command to ensure contractor misconduct will be successfully prosecuted after his departure from Iraq.” – Officer Evaluation, Major, 2008

 “Cal single-handedly managed the MNC-I civilian misconduct program, serving as the primary liaison with counterparts in MNF-I, CENTCOM, DOS and DOJ. His professional maturity and legal skill are the primary reasons for the overwhelming success of the Command’s efforts to prosecute and punish the rising number of civilian misconduct cases in the Iraqi Theater of Operations.” Officer Evaluation, Colonel, 2008

In part for this work, Cunningham received the Bronze Star Medal and the General Douglas MacArthur Leadership Award, one of the Army’s top awards for leadership.

1st Special Forces Command (Airborne): 2009 – 2012

After returning from Iraq, Cunningham transferred to 1st Special Forces Command (Airborne) as a Reserve Augmentee. During his time with the command, he was attached to and supported 7th Special Forces Group (Airborne) and 3rd Special Forces Group (Airborne) at Fort Bragg.

In July 2011, Cunningham deployed to the Combined Joint Special Operations Task Force – Afghanistan in support of Operation Enduring Freedom where he established the position of Deputy Command Judge Advocate. 

 “Cunningham is in the top 5% of Captains with whom I’ve served… Cal provided critical legal support to a joint task force of over 5500 personnel from 5 countries…that conducted 45 operations. In support of these operations, he reviewed 108 Level-I direct action joint contingency operations plans, and provided guidance on complex Rule of Law issues.” – Officer Evaluation, Major, 2011

Cunningham was promoted to Major in May 2012, and in 2013 he transferred to the 134th Legal Operational Detachment where he served as a Team Leader. 

U.S. Army John F. Kennedy Special Warfare Center and School: 2016 – 2019

In 2016, Cunningham transferred to the U.S. Army John F. Kennedy Special Warfare Center and School where until recently he served as the Deputy Staff Judge Advocate (DIMA) and helped train special operations forces in various phases of their curricula and professional development. 

 “With exceptional creativity and educational insight, MAJ Cunningham rewrote and fully developed a new LOAC [Law of Armed Conflict] training brief for use in all USAJFKSWCS professional training courses, using modern vignettes and a scenario based training methodology. .… Cal served with a remarkable, self-sacrificing attitude that automatically engendered trust among every commander and staff officer he worked with. Showing incredible flexibility, he easily pivoted between fiscal law issues, environmental law matters, and sexual harassment cases, never missing a beat.” – Officer Evaluation, Lieutenant Colonel, 2017

 “MAJ Cunningham is …the best JAG Major I’ve worked with in 29 years of service. Physically fit and mentally tough, Cal is an officer and attorney with both superior skill and intellect, who will benefit the Army, at all levels, long into the future.” – Officer Evaluation, Colonel, YEAR

In 2020, Cunningham continues to serve in the rank of Lieutenant Colonel as a Team Chief with an Army Reserve unit that trains one weekend a month.

Lieutenant Colonel Cunningham has received the following decorations and awards

Bronze Star Medal

Meritorious Service Medal with Two Oak Leaf Clusters

Army Commendation Medal with Three Oak Leaf Clusters

Joint Service Achievement Medal

Army Achievement Medal

Army Reserve Components Achievement Medal with Four Oak Leaf Clusters

National Defense Service Medal with One Star

Afghanistan Campaign Medal with One Campaign Star

Iraq Campaign Medal with Two Campaign Stars

Global War On Terrorism Service Medal

Armed Forces Reserve Medal with M Device, Third Award

Army Service Ribbon

Army Overseas Service Ribbon, Second Award

Army Reserve Component Overseas Training Ribbon

NATO Afghanistan Service Medal

Parachutist Badge

General Douglas MacArthur Leadership Award