Political hopeful Travis Montgomery turned to his brother Jackson, a lawyer, to manage his bid for office, but Jack came to town with his own agenda. Jack, who blamed Travis for a childhood accident that caused their sister Christine’s death, purposely mismanaged campaign funds and cost Travis the election. Jack also caught the eye of Travis’ wife Erica Kane.
Jack was thrilled when Erica, who was now divorced from Travis, accepted his marriage proposal, but his happiness was short-lived. Erica was drawn back to Travis over their daughter Bianca’s illness. After Erica tried to date both brothers at the same time, Jack forced her to choose between them. Erica remarried Travis.
Jack and Erica picked up their affair when Erica’s marriage to Travis hit the rocks. When Travis found out, he used his wife’s infidelity to sue for full custody of Bianca and took Erica to court. Erica urged Jack to deny under oath that they were involved, but Jack refused to lie. Erica ended their relationship.
Jack found love again with Laurel Banning, a woman with a shady past. When Laurel’s ex-husband Denny came to town making serious threats, Laurel killed him in self-defense to protect herself and their autistic daughter Lily, and hid his body with Jack’s help. The couple ran to escape the authorities and were wed. Jack and Laurel were later brought back to town and were cleared of all murder charges. Jack adopted Lily, whom he had grown to love as his own daughter.
When Laurel fell in love with Trevor Dillon, good-guy Jack quietly stepped out of the picture so the new couple could be together.
Jack and Erica grew close again while helping Bianca with her battle against anorexia. Soon after they announced their engagement, Erica’s old flame Mike Roy, who she thought was dead, came back to town. Jack once again found himself forcing Erica to choose between himself and an ex-love. This time, Erica chose Jack. But before Erica committed herself to Jack, she spent one last night in Roy’s bed. Jack caught the two together and called off the engagement. Erica was out of Jack’s life, but a new woman was entering it: his sister. At first Jack refused to believe that Kit Fisher was really Christine Montgomery, but a DNA test later proved that Kit was the sister that Jack thought had died during childhood.
Jack and Erica gave into their attraction once again, in spite of Erica’s relationship with Chris Stamp. Chris discovered their affair, and his associate Evan Flanders shot Jack. While Jack was in the hospital, Erica promised to marry him. Jack lost a lot of blood from the shooting and received a transfusion from Greenlee Smythe. The blood match revealed that Greenlee was Jack’s biological daughter from his long-ago affair with Mary Smythe. Erica found out about Greenlee’s paternity, but kept it from Jack. Greenlee finally told Jack the truth on his wedding day to Erica. When Jack realized that Erica had lied to him, he called off the wedding. While Jack didn’t gain a wife, he did gain a daughter — and a son, when he later adopted street kid Reggie Porter.
On the stand at Kendall Hart’s trial for the murder of Michael Cambias, Jack admitted that he had planted drugs in Michael’s home to see him punished for raping Bianca. Jack and Erica found their way back to each other again, but their engagement did not last long this time either. Erica withdrew from Jack after she discovered that he had kept Bianca’s pregnancy a secret from her. Erica turned to the bottle, and Jack grew more and more worried about her drinking problem. Jack arranged an intervention and called upon Erica’s daughters Bianca and Kendall, friends Opal and Myrtle, and brother Mark for help. Meanwhile, Jack’s adopted daughter Lily came to live with him.