Jack's villain days began in 1988 and were tamed in mid-1989. His main targets were Steve, Kayla, and Diana. Jack's darkest days called for a character redemption, and he was redeemed in his interaction with his real family, but mostly in his relationship with Jennifer. Jack and Jennifer's relationship would never have been as incredible or dyanamic as it was if not for Jack's need of changing. This is not to say that what he did in his villain days was right, but in the world of soaps, "the good girl and the bad little boy" (Jack, 1990) can find a way. The beauty of Jack and Jennifer's love story is wrapped up in how she saved him. Jack once told her when they were married; "You're like a... you're like a vital organ in my life. You're like something that I can't live without anymore. It's scary but it's wonderful too. I think about my life, if that's what you can call it, before we met, and what it would be like without you now, and it's... it's nothing."

Jack's adoptive father Harper framed Melissa Anderson for poisoning Kayla in 1988. Melissa was in love with Jack at the time, and the cops found in her apartment love letters she had written to Jack, as well as poisoned pills that matched the pills used to poison Kayla. She was arrested at the Deveraux New Year's Eve party. Harper had been poisoning Kayla because he thought she had the adoption papers that proved Jack wasn't a Deveraux; he framed Melissa to take the blame away from himself. When Jack learned about Harper's true nature later on, it was a definite factor in Jack's evolving opinion that he was no good, that he was just like Harper. It also devastated him to find out that the man he had loved as his father his whole life was such a monster.

Kayla Brady had agreed to marry Jack while he was battling Hodgkin's Disease; he had said that having her would give him the strength to live, and Steve Johnson, who know Jack was really his brother, pushed Kayla to Jack in hopes of saving him. Kayla never fell out of love with Steve, and avoided consummating the marriage with Jack. Eventually, Steve and Kayla began seeing each other behind Jack's back, and planned on telling Jack that Kayla wanted a divorce after Jack won his election as Assemblyman. Steve wanted to wait until then because he knew Jack would have something to live for in politics after Kayla left him if they waited until he had won. Unknown to them, a reporter took pictures of them during some of their secret meetings, and on the night of the election, after Jack had won, the reporter gave the pictures to Jack. He looked through them, shocked and devastated.

When they got home after the celebration party, Jack was acting erratic and aggressive. He started kissing Kayla roughly, and she pushed him away. Jack confronted Kayla about the pictures, and he told her how at first he had thought the pictures were fake. She tried to call Steve so that the three of them could talk, but Jack wouldn't let her and demanded to know if she had slept with Steve while married to Jack. When Kayla didn't answer, Jack knew, and was furious. He told her that she was his wife and he was going to make love to her. The confrontation led to Jack raping Kayla.

After the rape, Kayla went to Steve, and the went out of town. While in the woods, she told him what Jack did. Steve was furious, but Kayla convinced him not to go after Jack right then. Jack meanwhile found out where they were, and sent a man to beat up Steve in the woods. While Steve was being beaten up, Jack confronted Kayla in the cabin she and Steve were staying in, and forced her to come with him by threatening Steve's life. For the next few days, Jack kept Kayla locked in the loft, threatening to do something to Steve if she tried to escape. He believed that eventually she would accept that she had to stay with Jack, and he wouldn't have to lock her in anymore. One night, Kayla was standing on the roof, and Steve surprised her. He had finally been able to get home, and he was going to take Kayla away from Jack. While they were talking on the roof, Jack came up and saw them. He grabbed Kayla, (see picture above) and then he and Steve began fighting. The fight led to Jack falling off a fire escape stories below. Jack then needed a kidney transplant, and Steve donated his, knowing they were brothers and feeling responsible for what had happened. Eventually, Kayla pressed charges against Jack for rape, and filed for divorce. Jack got off the charges with no jailtime, and after finding out that Harper was the Riverfront Knifer and had tried to kill Kayla three times, Jack gave her a divorce.

After Kayla and Steve got back together, Jack turned his attention to Melissa Anderson, who had been in love with him for some time. She had been accused of poisoning Kayla to have Jack for herself, but the charges were eventually dropped. Melissa was the only non-related person in Salem who wasn't totally disgusted with Jack. Melissa's adoptive parents, Mickey and Maggie Horton, were totally against Jack and Melissa's relationship, and so the two began seeing each other in private. Melissa knew the truth about Jack's family because she had found his adoption papers, and so after awhile, she wanted to tell Jack about them. One night, Melissa brought Jack to her place to show him the papers, but Steve Johnson was already there, trying to burn them. Jack grabbed the papers, and read them in disbelief. Melissa was also there for Jack when he found out that his father was a murderer. After Steve and Kayla's wedding, Jack and Melissa slept together, and Jack promised her that he wanted her and not Kayla anymore. Jack was lying, and didn't really love Melissa, but Melissa was totally clueless.

Jack began preparing to run against Mickey for the Senate seat that Harper had left empty, and he used his relationship with Melissa to give himself an edge. He also continued to torment Steve and Kayla by hurting their cause for the Community center. Melissa was often unsure about Jack's motives, but she loved him and didn't want to believe the bad about him. Everyone kept trying to tell her the truth about Jack, but she was stubborn and the two got engaged. She finally saw the light when she saw Jack's behavior with Kristina Andropolous, and figured out that Jack was cheating on her and never really loved her.

Melissa didn't say anything to Jack about what she knew, and instead prepared for their wedding. She enlisted the help of Marcus, who was serving as best man. Melissa went as far as to walk down the aisle and stand in front of the minister with Jack, and when the opportunity came, Melissa announced that she didn't want to marry Jack. She told him off in front of everyone, and threw her boquet in his face. With that, she left him at the altar, her family cheering. Jack was humiliated, and ended up losing the election for Senate (Mickey did not win either, thanks to some of Jack's dirty campaign tactics).

The one person who stood by Jack from the very beginning, who loved him unconditionally, was his mother, Jo Johnson. After he found out he was really a Johnson, Jack denounced his roots and said he'd rather die than be Billy Johnson. Jo was heartbroken but still loved her son, even after she found out what he did to Kayla. On Christmas 1988, Jo gave Jack a picture of her holding him when he was a baby, and wrote on the back: "To my son - I loved you then. I love you now. Merry Christmas - Mama." Later, Jack was cajoled into dressing up as Santa Claus for the hospital party, and disguised, he gave Jo a present anonymously. To himself he called her 'Mama', though he never called her anything but Mrs. Johnson to her face. Despite his slimy ways, he still was vulnerable around his mother.

Jack continued to make trouble for Steve and Kayla into 1989. He caused trouble for the community center Kayla was so devoted to, and was behind a threatening letter sent to Kayla about the research she was doing. The research was inevitably going to uncover a scandal Jack was involved with, and he wanted to keep it from being leaked. Jack also could not help bugging Steve. When Steve got a job at Saxton's, Jack showed up and caused trouble, causing Steve to get fired. When Jack noticed Kayla's friendship with Mike Horton, he tried to get Steve jealous of the two, but it didn't work. Jack still had feelings for Kayla, and after agreeing to eat dinner at Jo's with Steve and Kayla, Jack backed out when he found out Kayla couldn't make it. Jo was really disappointed that Jack had cancelled, and so Steve went after him and forced him to go. Jo was very pleased to have Jack there, and tried to tell him that his family cared about him. Jack left, and once outside the door, appeared very emotional about his mother's love for him.

While unaccepting of his real family, Jack tried desperately to strengthen familial ties with his stepmother Anjelica and her new son, Alexander. Jack had his hopes set on being named Alexander's godfather, thus making him closer to the family, but Justin received the honor instead. Nonetheless, Jack still looked at Alexander as a brother, and after the Christening, Jo overheard Jack talking to Alexander in his crib about being his brother. Jo told Jack that he already had a brother - Steve. Jack felt that Alexander wouldn't hate him and that he could start from scratch with the baby. Jack seemed to regret the fact that Steve and he did not get along, but he couldn't help egging on the rivalry, and didn't have any intention of apologizing first.

When Diana Colville, the publisher of the Spectator, started leaking out small bits of information about Jack in the newspaper, Jack anonymously bought 51% of the paper. When he revealed himself as the buyer, he started taking control of the paper to keep information about himself out of it. It was revealed that Jack owned a company that was responsible for the toxic dumpings that caused some Salem High kids to get rashes. Diana was set to go public with the information, and so Jack went ahead and revealed that he owned the company, said he hadn't known about it until recently, and took steps to take care of the problem. Diana was furious that Jack had turned the situation around to make himself look good. Jack developed a desire to make trouble for Diana, and he found the perfect opportunity when the story of an MIA that had been found came up and Diana didn't want to do the story on it. Jack found out that the MIA was Cal Winters, and that Diana had once been involved with him. Jack took steps to get Winters back in Salem, and then let nature take its course. It turned out that Cal and Diana had been engaged 5 years prior, and eventually, Diana left Salem. Jack was then the publisher of the paper and in control. After all this, Jack became more involved with Jennifer, and their story progressed from there.

Thanks so much to Ken from Who's Who In Salem for the following screen caps.

Jack's past was a powerful hindrance in his and Jennifer's relationship, because Jack was unable to forgive himself or let Jennifer love him when he felt so unworthy. After Jack had finally been able to let Jennifer love him, and show her his love for her, they were hit with a shocking blow. Jennifer, who had been posing as the fiancee' of Lawrence Alamain, was raped on the night of her faux marriage to him. For a long time, Jennifer could not bring herself to tell Jack what happened, but rather grew more and more distant from him. One night, Jack took Jennifer out of town to a country inn where he tried to get closer to her. As he kissed her, Jennifer flashed back to the rape, and struck Jack, shouting, "Don't touch me you rapist!" As soon as it happened, she realized that she had reacted to her flashback, but Jack had no idea that she wasn't talking about him. All his fears and insecurities about how Jennifer could deal with his past came back in an instant. All their hard work to be together seemed to be negated in one second. Jack broke off the relationship, believing that Jennifer thought of him as the person he had been when he had raped Kayla. Eventually, Jennifer told Jack what had happened to her, that Lawrence had raped her, and that she hadn't been talking about Jack that night at the inn. Jack was horrified that she had experienced the violence he had inflicted on someone else, and did not see how they could be together. He asked her if she could forget what he had done, and she said no. He took that to mean that they had no future, but Jennifer tried to make him see how she felt:

Jennifer: You know Jack, for a long time I pretended not to see that side of you. I didn't want to hear about and I didn't want to think about it. All I wanted to think about was the good things, the things I love about you. But then I realized that if you love somebody, you have to accept everything about them. You can't take the good and ignore the bad. And what we had together was so good, Jack. I don't want to live without that... I don't know if I can.

Jack: I don't know how you can say that sort of thing - when you look at me, you see Lawrence.

Jennifer: I do not see Lawrence! All right - after Lawrence raped me Jack, I wanted to die, all right? But I didn't. Something inside me did - and the only time that I feel alive and happy is when I'm with you! That's what kept me going through all of this, was the thought of being with you again - you kept me going! So when I look at you, I don't see Lawrence. All I see when I look at you is our future together.