Cal Winters was an army lieutenant who was believed to have been dead. Much to Diana Colville's dismay Cal was very much alive, and showed up in her office at the Spectator days before she was to marry John Black / Roman Brady. Cal was sick, and was admitted to the hospital but he would live. Diana rushed her wedding to John/Roman but Cal crashed it and claimed to be her husband. Diana tried to prove that Cal wasn't her husband but he insisted he was. Eventually he admitted their marriage never happened, but he refused to give up on Diana. Cal came over to John/Roman's place with a gun and got into an argument. A gunshot went off and John/Roman was hit. Cal was arrested and John/Roman remained in a coma for some time. Cal knew that he was innocent and that it was Diana who shot Roman by accident. Diana fled town and Cal was released from prison.

Cal became a private eye, and became close friends with Kimberly Brady, and eventually lovers. Cal was helping Kim overcome her grief of the death of her husband Shane, not knowing he was very much alive. When Cal and Kim finally made love Kim's first husband had returned home and witnessed everything. Meanwhile Cal gained his first client, and undercover agent named Renfro who was looking for Arthur Downey. Cal became obsessed with Kimberly. When Shane returned he threatened his chances with Kimberly. Cal made it appear that Kimberly was in danger and faked some break-ins to her house, and provided her with a gun. When Shane finally returned home, Kimberly shot him. Despite Cal's best efforts Shane and Kim made up. When Rebecca Downey was going to confess everything to Kimberly and Shane, Cal killed her. Cal then kidnapped Kimberly at took her to a mountain cave. Shave saved her, and Cal was sent to prison.

Cal's schemes didn't end in prison. Cal learned Kim was pregnant and he used this to his advantage. One of the doctors at Salem Hospital was an old army buddy Cal's, and he had incriminating evidence on him. Cal blackmailed the doctor into telling Kimberly the baby was not her husbands. Kimberly considered having an abortion, but was stopped by Shane after Cal had told him Kimberly was pregnant. The strain was too much for Kimberly and Shane, and they did break up. Cal however was not through. Cal managed to break out of jail and kidnap Kimberly and Kayla. He threatened to kill them both, but they were saved and Cal was recaptured. At the hospital Kimberly gave Cal a sob story about how their daughter Jeannie had been hurt and needed a blood transfusion immediately. Kimberly's trick worked, Cal told her that he couldn't give blood because Shane was Jeannie's real father. Cal was then sent back to prison, never to be heard from again.