Jackson arrived in Pine Valley to help run his brother Travis' campaign for Senate. Jack had accepted campaign bribes and juggled Travis' books in order to lose the campaign to repay Travis for a childhood event that had led to their sister Christine's death. Jack had always been blamed for the boating accident, when, in reality, it had been Travis who had caused her death. Travis had always been the smart one and Jack the black sheep in their southern, matriarchal family.
Jack fell in love with his sister-in-law, Erica, and the two had an affair. When Travis found out, he divorced Erica and won sole custody of Bianca, their daughter. Erica's love for Jackson died when he refused to lie about their affair on the witness stand at the custody trial. Jackson and Erica's love was rekindled several times, but none were permanent. Jackson united with Brooke English during the time of Dimitri and Angelique Marick's problems. They had a brief romance and remained good friends afterward.
One night while driving, Jackson's headlights shone upon a gorgeous blonde, Laurel Banning. [Note: The original Laurel was blonde, but the role was recast and the subsequent Laurel was a brunette.] She later turned to him for help; they fell in love and moved in together. Jackson grew to love Lily, Laurel's autistic daughter by her previous, demented husband, Denny. When Denny arrived in Pine Valley and threatened Laurel's life and custody of Lily, Laurel killed him in self-defense. Jackson helped Laurel hide the body in the Marick mineshaft. Upon the discovery of the body, the truth was revealed, and Jack was disbarred for six months.
Laurel's previous history as an embezzler and thief in order to keep Lily in a special school for the autistic was kept hidden until Laurel's embezzlement in the Mason Foundation -- Natalie's Foundation -- caused Natalie to lose her life. Trevor became very close to Laurel as she tried to help him with his anguish over Natalie's death. They fell in love. Jackson graciously bowed out and divorced Laurel, leaving her free to marry Trevor. Being free with time on his hands, Jackson turned to his second love, the law. He took on many high-publicity cases, such as the Louie Greco trial, and thus won the election for Pine Valley's District Attorney.
Jackson was Erica's attorney for her kidnapping trial. Even though she was sent to prison, Jack still had a place in his heart, as always, for Erica. Jack visited her often and stood by her side during the tough times. When Bianca arrived in Pine Valley and was diagnosed with anorexia nervosa, Jack made sure he told Erica of Bianca's health progress. When Erica was released from prison, Jack declared his love for Erica -- again -- and Erica could not be any happier.
Erica and Jack's love life took a turn for the worse when Erica's former beau, Mike Roy, returned to Pine Valley from the dead. Mike had been forced to stage his death over a dozen years prior as part of an FBI project. Erica still had deep feelings for the love she thought she'd lost. For months, Erica was torn between Mike and Jack. Jack fought long and hard for the woman he loved, but he could not forgive Erica for sleeping with Mike in what he called "the obligatory horizontal goodbye." Erica had chosen Jack, but Jack hadn't chosen her. Erica tried her best to win back Jack, but he wouldn't take her back.
Jack remained idle for quite some time, appearing as a comforting and understanding uncle to Bianca after she "came out." Jack returned to the limelight in the winter of 2001 as the lead prosecutor in a murder case against Erica Kane. Erica stood trial for killing Frankie Stone. Jack seemed to take his personal frustration out on Erica, and the trial quickly became little more than a three-ring circus. Erica was found not guilty, and Jack was left with a slightly tarnished reputation. Afterwards, Erica tried to cozy up to Jack again, but Jack adamantly refused any and all of Erica's advances.
Jack eventually could no longer deny his feelings for Erica, and not long after adopting teenager Reggie Porter, Jack and Erica married in a beautiful ceremony. Jack began to settle into life as a father. Not only did he have Reggie and recently discovered daughter Greenlee, but Lily also returned home, but was furious when Lily got involved with Jonathan Lavery. Jack became upset when he found out that Lily, who had just turned 18 years old, had married Jonathan Lavery. He decided to have Lily declared incompetent at a hearing so that her marriage to Jonathan would be null and void. At the hearing, Jonathan spoke to Jack privately and admitted to Jack that he had faked being "slow" and would tell Lily the truth if Jack dropped the incompetency petition. Jack agreed, and Jonathan and Lily divorced on their own.
Jack had problems in his own marriage to Erica Kane, since she had gotten involved with her ex-husband, Jeff Martin. This led to Erica moving out of her home with Jack and into the Valley Inn. She and Jack co-hosted a talk show called He Said, She Said, where they spoke about advise for people in relationships. Despite how Jack and Erica appeared to be getting back together, they divorced.
Jack promised Erica that he would help her out when she was arrested for insider trading by U.S. District Attorney Sam Woods. Sam was running to be U.S. Senator of Pennsylvania, and both Jack and Erica feared he would use Erica's arrest for publicity. Erica devised a plan to plead guilty so Sam could not use her for his advantage. Erica was sentenced to prison. Jack and Sam eventually worked together to get Erica released from prison early, since she was a model prisoner, having helped many of her fellow inmates get job skills and to see their families more often. On the day, Jack went to the prison to take Erica home; an inmate named Sable, who claimed that Erica had slept with her husband, held Erica hostage. Erica managed to free herself from Sable, and Jack took her home.
Jack started to date Erica's friend and fellow inmate, Carmen Morales, with Carmen's permission. Their relationship never went beyond a few dates.
Jack was distraught when his daughter, Greenlee Smythe, went over a cliff and was presumed dead. Ryan Lavery and Kendall Hart Slater went to Connecticut to identify a body that had been found. They confirmed that the body was Greenlee's without looking at the body. In the morgue, Ryan saw the ring he had given to Greenlee and told the attendant it was Greenlee's body. However, DNA results confirmed that Greenlee's DNA and that of the dead body in the morgue were a match. Jack had Greenlee cremated and scattered her ashes out to sea.
Erica tried to support Jack in grieving for his daughter, but he chose to leave Pine Valley to mourn Greenlee alone. When Jack returned, a rift formed between him and Erica when he learned it was Erica's daughter Kendall that had run Greenlee off the road. Jack refused to represent Kendall when she was accused of the murder of Stuart Chandler, and he left town again. While he was gone, Erica entered into a brief relationship with Ryan Lavery, but Erica ended the affair when Jack returned.
Jack and Erica tried to rekindle their romance, but they faced another hurdle in their relationship when Greenlee returned to Pine Valley. Greenlee had survived the car accident due to the care she received from David Hayward. Greenlee had been critically injured and required a risky surgery to recover. Instead of allowing her family to know she was alive only to risk losing her again, Greenlee chose to let everyone believe she was dead until she had recovered from the surgery. Jack was overjoyed by Greenlee's return, but his joy was overshadowed by his disappointment in Greenlee's decision to marry David Hayward.
Greenlee was determined to exact revenge on Ryan and Erica to punish them for their affair, even at the expense of her father's happiness. Greenlee joined Erica at the helm of Fusion, and the two were at constant odds. Both Erica and Greenlee vied for Jack's sole attention, and each tried to turn Jack against the other. Jack initially sided with his daughter until he realized how much Greenlee had changed. Erica went missing after her plane crashed, and Greenlee withheld information about the plane crash to protect David.
Jack leaned on his friend Krystal Carey while Erica was missing. Eventually, Krystal and Jack found Erica in Pigeon Hollow, being cared for by Caleb, a mysterious mountain man. Caleb moved to Pine Valley when his uncle, Palmer Cortlandt, passed away. Palmer's will required Erica to assist Caleb in running Cortlandt Electronics for one year. Jack was suspicious of the growing connection between Caleb and Erica, but he proposed to Erica, and she accepted.
Erica kept putting off setting a wedding date, but when Jack questioned her about her feelings for Caleb, Erica convinced Jack to go on a pre-wedding honeymoon. When they returned, another wedge formed between Erica and Jack when Kendall needed heart surgery. Erica arranged for David Hayward to receive a full pardon for his crimes in exchange for performing surgery on Kendall. Jack asked Erica to back out of the deal after the surgery had been completed because David had caused Greenlee so much pain, but Erica refused.
Erica continued to grow closer to Caleb, and Jack shared his concerns with Krystal. Erica became jealous when she realized Krystal had developed feelings for Jack, so Erica set a wedding date. Jack and Erica were to be married in St. Barts, but Erica never made it to the altar. Erica disappeared from the wedding, but she called Jack later and explained she could not go through with marrying him. Jack was distraught until he and Caleb found evidence that Erica had been kidnapped. Caleb and Jack worked together to rescue her.
Erica and Jack reunited when Erica revealed the kidnappers had forced her to make Jack believe she had left him. Although Erica was physically fine after the kidnapping, she acted strangely and was reluctant to discuss anything related to the kidnapping. Although Jack was unaware of it, the woman he believed was Erica was really Erica's kidnapper, Jane Campbell. Jane had undergone plastic surgery in order to look like Erica and inserted herself into Erica's life while the real Erica Kane remained a prisoner.
Jack did not press "Erica" about her ordeal but he found it strange that she seemed disconnected from Bianca and Kendall. Both women had turned to their mother for support after they learned that Ricky Torres, the man that had been briefly engaged to Kendall, had been involved in the death of her husband Zach. Ricky had also kidnapped Bianca and tied her up, which caused Bianca to have flashbacks of her rape. Jack scolded "Erica" for not putting her own issues aside for her children. Jack's concern increased after he found "Erica" about to throw away her sobriety by sneaking a drink. Jack, along with "Erica's" close family and friends staged an intervention to confront her about her recent behaviors, the latest of which included partnering with David Hayward to purchase Pine Valley Hospital and naming him as chief of staff. They explained the trust she placed in David was more dangerous than drugs or alcohol. "Erica" shocked everyone at the intervention when she professed her love for David and accepted a marriage proposal from him. Jack told "Erica" she needed professional help from a therapist and stormed out.
Jack was reunited with the real Erica at ConFusion and he watched her stab David with a knife. Erica said that she had been kidnapped by a woman who had undergone surgery in order to impersonate her and David had known the woman was an imposter. David convinced Jack and the police that Erica was mentally unstable and had suffered some sort of breakdown. Erica was taken to Oak Haven for a psychiatric evaluation and she was admitted. While Erica was in Oak Haven, Jack investigated Erica's claims that she had been held hostage while her doppelganger took over her life. He told Erica he believed in her and he tracked down Jane Campbell. Jack convinced Jane to return to Pine Valley to confess to kidnapping Erica, although Erica wanted to allow Jane to go free. Jane surprised Erica and Jack when she voluntarily confessed to stabbing David. She went to prison for a crime she had not committed to make amends to Erica for what she had done.
The charges against Erica were dropped and Jack took advantage of Erica's freedom. He took her on a romantic trip to Paris. Their trip was cut short when they received the news that Kendall's presumed-dead husband Zach was alive. David had used his experimental Project Orpheus treatment to save Zach after his plane went down. David hinted to Erica that he had also saved someone she loved.
Erica believed that David might have her former lover Mike Roy hidden away somewhere. Erica planned a trip to L.A. to search for Mike under the guise of promoting her new book. Jack saw through Erica's story and confronted her in L.A. She reminded Jack she had chosen him over Mike years ago and had always chosen Jack since. He admitted he knew Erica was committed to him but he occasionally needed a reminder. He flew back to Pine Valley after Erica promised she would return home soon to plan their wedding.
When Erica returned to Pine Valley, Jack hoped she would focus on their wedding but instead she took on a new project. A director had asked her to co-produce and star in the movie adaptation of her latest book. Jack was not thrilled with the idea but he and Erica tabled the discussion and attended a family barbeque at Zach and Kendall's home.
After the barbeque, Jack and Erica returned home but were soon interrupted by the movie director Kit Sterling. He told Erica she needed to board a plane to L.A. immediately and would be there for three months. Erica dismissed Kit and told him she needed to discuss everything with Jack first. Jack knew Erica had already made her decision to go and she assured Jack she would plan their wedding right after the movie. He told Erica something always came before their relationship and he was done living that way. He proceeded to walk out on Erica.
Jack moved out of Erica's penthouse and he attended a party hosted by Adam Chandler to welcome home Adam's brother Stuart, another presumed-dead resident of Pine Valley that David had saved. Erica also attended the party and she asked to speak with Jack privately. Jack listened as Erica explained that he could move to L.A. temporarily so they could spend their nights together after she worked all day on the movie set. Jack told Erica he did not want to spend his life watching her chase her dreams while he sat on the sidelines and he accused her of not wanting to be married. She admitted he was right.
Jack wished Erica luck and he walked away from her. Erica followed him through the party and begged him not to leave her because she needed him. Jack responded by telling Erica he no longer cared what she needed as a gunshot was fired.