Craig, who first appeared in the fifth season, was a brash advertising executive who worked at the D&D advertising agency. In time, he became romantically interested in Amanda Woodward, who remained committed to her husband Peter. During a period in which the spouses were separated, Craig led Peter to believe that he'd slept with Amanda, which eventually brought the marriage to an end. Amanda then slept with Craig, but later rejected his desire for a more committed relationship.
Craig later fell in love with Sydney Andrews, who he started his own ad agency with to combat Amanda's. At Craig and Sydney's outdoor wedding, Sydney was struck and killed by a car, leading Craig into depression. He was later comforted by and began a relationship with Jennifer Mancini. In time, however, his unfaithful actions brought this relationship to an end, and a series of other problems began to mount. Craig ultimately committed suicide by shooting himself, stating that he missed Sydney.