Crockett was married to Caroline, with whom he has a son, Billy. Due to the stress brought on by Crockett's profession - working as an undercover vice detective, "living the life" away from home to maintain his "cover", Caroline filed for divorce in 1984 and planned to move to Atlanta with Billy. However, due to increasingly bitter legal process, he and Caroline decided to fire their lawyers and give their relationship one more shot. However, after they (with Billy) barely survive a hit by assassin Ludovici Armstrong, who was hired by Calderone to kill Crockett, Caroline really realizes the stress and dangers of his job and they agree to divorce, and Caroline and Billy move away. Crockett would not then see Billy for three years, until he goes to see him after accidentally shooting a 13-year old child who drew a gun on him. Around the same time, Crockett was assigned with protecting pop singer Caitlin Davies, who was scheduled to testify against her former manager Tommy Lowe. Though at first Crockett and Davies clashed over their professions, they ended up falling in love after Crockett saved her from a hit by Lowe's hitmen, and they got married, buying a house and agreeing not to let each other's careers interfere with their lives.