Craig grew up in a blue-collar, Irish-Catholic family in Wickford, Rhode Island. He was an all-state wrestler at Bishop Hendricken High School and received his nomination to the U.S. Military Academy from the late Senator John Chafee. As a cadet, Craig studied history and was a member of the sport parachute team, completing over 450 freefall skydives and earning a professional performance rating. He graduated West Point in 2000 and was commissioned in the United States Army. After completing Ranger School, Craig continued to the University of Oxford on a Rhodes scholarship. At Oxford, he completed two masters degrees, rowed for Lincoln College, and played on the university lacrosse team.
In 2003, Craig led an infantry rifle platoon along the hostile border between Afghanistan and Pakistan with the 10th Mountain Division as part of Operation Enduring Freedom. His platoon operated along the entire spectrum of military operations—from humanitarian assistance with the first Provincial Reconstruction Team established in Afghanistan to combat engagements against Al Qaeda and the Taliban. Following his return to the United States, Craig joined the elite 3rd Infantry Regiment, “The Old Guard,” in Arlington, Virginia, responsible for Arlington Ceremonial burials, the Tomb of the Unknown Soldier, and defense of the National Capital Region. He served for three years as the Army Exchange Officer to the history faculty of the U.S. Naval Academy in Annapolis, Maryland where he focused on American foreign policy and directed the international scholarships program.
After leaving the military, Craig served as a national security adviser on Barack Obama’s presidential campaign, led veterans outreach efforts in western Pennsylvania, and was the Chief of Staff for the President-elect’s Department of Defense Review Team. Craig’s military decorations include the Bronze Star, Army Commendation Medal with “V” device, Combat Infantryman’s Badge, Ranger Tab, and Parachutist Badge.