It is known that in 1993 John joined the U.S. Army to avoid a jail sentence, where he served as an Infantryman, Ranger and Special Forces soldier with the 1st Special Forces Group, before discharged as a Sergeant First Class after 12 years of service. While he was stationed at Fort Lewis, Washington in 2001, John met Jessica Arndt, a nurse with whom he fell in love. On a vacation to Mexico, he tells Jessica that he has left the Army just as Jessica witnesses the Twin Towers fall on television, and they both realize his career is far from over. Eventually, John breaks up with Jessica, and is recruited by the CIA. Some time after that, they meet by chance in an airport, where a newly engaged Jessica gives John a final opportunity to save their relationship by asking him to ask her to wait for him; he is unable to do so.