1987: Since his childhood, Jackson Montgomery had always felt inadequate compared to his brother, Travis Montgomery. He had left his home in Charlotte, North Caroline early on to make his own name away from Travis. Jackson became a successful attorney with a equally prevalent reputation of being a playboy.
Jackson Montgomery took a break from his life as a public defender to work full time on Travis’ senate campaign. Unfortunately, he saw the campaign as his meal ticket, and began mismanaging his funds to fuel his lavish lifestyle. When the truth of the matter came out, Travis was forced to resign.
Jackson arrived in Pine Valley after Travis married the mother of his child, Erica Kane. Erica was an incorrigible and selfish woman. Jackson thought Travis deserved her. Even though they could not be in the same room with each other without fighting, Jackson began to be drawn to Erica.

1988: Jack betrayed Travis again when he teamed up with Adam Chandler in his bid to buy out Travis’ company.

1989: Brooke English hired Jackson when she decided to divorce Adam. Jack used his knowledge from working with Adam to get Brooke half his fortune, and a sizeable portion for himself.
Travis’ amnesia caused him to think he was still married to Barbara. Erica turned to Jack with her concerns. The animosity they once shared turned to passion. They began an affair.

1990: Jackson proposed to Erica. Erica had been hesitant to set a date for the wedding date until she could explain to Bianca the situation. But, that had to be postponed when Bianca fell ill with Reyes Syndrome. It was the sight of her parents happily together that helped her recover. Jackson gave Erica an ultimatum: it was either Travis or him.
Travis asked Erica to remarry him for Bianca’s sake. Needing to put her child first, Erica revealed the devastating news to Jackson. On the day Erica and Travis were to remarry, Jackson arrived at the chapel to object. Erica pleaded with Jackson to just let her go.
But Erica and Jackson could not stay apart for very long. When Erica learned that Travis had been unfaithful with Barbara, Erica turned to Jackson again. Their affair was as passionate as ever.

1991: Bianca discovered Jackson and Erica’s affair. Travis used the affair as the basis for his custody suit. Erica begged Jackson to say that the night Bianca caught them was the first night they were together. Jack could not afford to perjure himself on the stand, lest he risk his career as a trial lawyer. But, Erica could not understand Jack’s situation. Jack admitted in open court to the affair. Erica blamed her loosing custody of Bianca on Jack.
Jack became romantically entangled with a very pregnant Brooke. They were coming back from a night on the town when a drunken Arlene Vaughan came crashing into his car. Jack was unconscious as the trauma caused Brooke to go into labor. Jamie Martin was born that night at the accident site.

1992: Jackson was weary of new Pine Valley resident Dimitri Marick. When Brooke did not was to investigate the matter any further, Jackson went on his own hunt. Jackson was one of the first people to learn of the existence of Dimitri’s comatose wife, Angelique Voynitzeva. Long thought to be dead, she was very much alive. Jackson befriended Angelique as she worried about the end of her marriage thanks to Dimitri's blossoming romance with Erica.

1993: Jackson became enchanted with a woman named Laurel Banning. Laurel became an outcast in Pine Valley when it was revealed that she had embezzled money from the Mason Foundation. Laurel had done this to keep her autistic daughter, Lily Benton, in a special school. Jackson had also found out Laurel was only on of her many identities. Laurel was really named Carla Benton. She changed her name in hopes of eluding her abusive ex-husband.
One night, Jackson found Laurel standing over a dead body. It was her ex-husband, Denny Benton. Jackson helped Laurel dispose of Denny’s body. They went on the run until they could prove that Laurel was acting in self-defense. For Jackson’s role in Laurel’s crime, his license to practice law was temporarily suspended. But, Jackson was now in love. He married Laurel and adopted Lily.

1994: Jackson and Laurel's marriage suffered greatly because of Jackson’s devotion to his job. He was busy defending Erica for allegedly trying to murder her newest husband, Dimitri Marick. Laurel had grown suspicious of Trevor’s new girlfriend Jane Cox and wanted Jackson to help her investigate.
Laurel found out that Jane was none other than Janet Green. Laurel got in a car accident that left her paralyzed. Janet had sabotaged her breaks. At the hospital, she revealed to Jackson her findings. Jackson rushed to Trevor with the news. He brought the evidence to Trevor moments before he was about to saw his vows to marry Janet.
The tension in their marriage caused Jackson to stray. He had a one-night stand with Erica. When he admitted the affair to Laurel, they decided on a divorce.

1995: Jackson teamed up with Belinda Keefer to defend her brother, Noah Keefer, when he was accused of murdering rapist Louie Greco. For his role in the high profile case, Jackson was appointed District Attorney.

1996: Jackson was forced with the difficult task of telling Lily about Laurel’s death at the hands of Jason Sheffield.

1997: Jackson played mediator between Travis and Erica when Bianca was diagnosed with anorexia. Travis wanted to keep Bianca away from Pine Valley because of all of the antics Erica had found herself in over the last year. Jackson was defending Erica after she was sent to prison for kidnapping Madelyn Grey. Erica was first to notice that Bianca was ill. She was not eating. Together, the Montgomerys staged an intervention in hopes of convincing Bianca to find help for her eating disorder. The ordeal brought Jackson and Erica together again.

1998: Jackson and Erica’s current engagement met a hitch when Erica’s former lover, Mike Roy, came back from the dead. He had spent the last decade undercover as a secret agent. Erica assured Jackson she was going to tell Mike it was over. Jackson learned that Erica had slept with Mike again. Jackson told her their chances together were over.
A stranger named Kit Fisher came to Pine Valley in search of Jackson. Jackson wanted to know what business she had with him. Kit claimed to be Christine Montgomery, Jackson’s late sister. Jackson refused to believe her. As a teenager, he watched helplessly as Christine drowned in a boating accident in North Carolina. The incident had estranged him from his family. Kit agreed to a DNA test, but Jackson was not ready to confront the traumas of his past.

1999: Jackson’s investigation into Kit’s past proved her claims. Kit was Christine. Jackson made it his mission to convict whomever had raped her. He made his battle against Ryan Lavery personal. Jackson would have got his conviction if Braden Lavery, Ryan’s brother, did not admit that he had slept with Kit the night of the rape. Because of Kit’s wrong identification, Jackson did not have enough evidence to indict Braden. He decided to take a leave of absence as District Attorney.
Travis invited Kit to spend time with him in Seattle. Jackson said goodbye to the sister he was only getting to know again.

2000: Jack had the hard role of revealing to Erica and Bianca that Travis died of a sudden stroke. Jack was unaware of the extent of difficulties Bianca was going through in her life. She revealed to Erica that she was a lesbian. Erica had a hard time coming to terms with Bianca’s sexual orientation. Bianca turned to Jackson for the support her mother could not offer her.

2001: Jackson was forced to prosecute Erica for the murder of Frankie Stone, Bianca’s new girlfriend.

2002: Jackson found himself at odds with new Police Chief Anna Hayward. Anna’s husband, Dr. David Hayward, and his family were under investigation for multiple crimes in Pine Valley including the Proteus drug scandal.

2003: Jack sunk into depression after visiting Lily at her school. Lily had fallen ill and there was nothing Jack could do to help her. Erica found out and wanted to support Jack. But the couple could not ignore their latent attraction. After a one-night stand, Erica made Jack promise to keep her silence to protect her new fiancée, Chris.
When Chris found out, he broke up with Erica. Evan Flanders misinterpreted Chris’ venting as an order to kill Jack. Jack was shot at SOS. Though the doctors were able to treat the original injury, Jack body went into shock a few weeks later. He needed a blood transfusion to survive. Greenlee duPres, the daughter of his old friend Mary Smythe, proved to be the only viable donor in Pine Valley.
Jackson took in Reggie Porter after his foster guardian, Trey Shepherd, went to prison for the Linden House arson. Jack had offered Reggie leniency on his larceny charge for evidence incriminating Trey. At first, Reggie was not too happy to have the District Attorney as his new guardian. But, Jack began to really care for Reggie. Jack asked Reggie if he could adopt him as his son.
Erica and Jack could deny their feelings no longer and made plans to marry. All seemed to be going smoothly until the day of the wedding. Greenlee stormed the chapel with startling news: she was his daughter.
Mary and Jack had a summer fling before college. Mary did not know Jack came from a good family, because he was still estranged from the Montgomerys after Kit’s supposed death. Greenlee also revealed that Erica had known the truth all along, and had blackmailed Mary to keep silent.
More devastating news came out when Bianca revealed Michael Cambias had raped her. Jack could not piece together a case as Bianca had burned any physical evidence of the rape. When Michael was found dead, Jack began to run interference to protect his family, many of whom were considered suspects in the investigation.

2004: Bianca confided in Jack that she was pregnant with Michael’s child. She was not ready to tell Erica because she had never really dealt with her own rape, or Kendall Hart, the child she had as a result. Bianca also realized she had killed Michael. With everything out in the open, Erica began to spiral out of control. She turned to alcohol to deal with her pain.
Bianca’s baby, Miranda Montgomery, died when the helicopter they were rescued in crashed. Bianca lashed out at her mother, and drove Erica out of town.
Jack had asked Livia to defend Kendall in the Michael Cambias murder trial. Little did he know, Reggie was harboring her runaway niece, Danielle Frye, in his apartment.
Lily asked Jack to be mainstreamed into public high school. Jack reluctantly agreed, and she moved in with him. One night, Erica arrived at the apartment looking for Jack, drunk. In her lucid state, she startled Lily and sent her into a panic. It was the last draw for Jackson. He staged an intervention to save the woman he loved. Erica’s alcoholism stemmed from her never dealing with her own rape when she was 14. Erica revealed her father had traded her to an actor named Richard Fields so that he would star in his next movie. Admitting the truth was the first step Erica needed to deal with Bianca’s rape, and accept Kendall as her daughter.
When Erica came out of rehabilitation, Jackson proposed to her again. The same night, they learned that Miranda was alive. She had been switched at birth with Babe and JR Chandler’s son. Jackson accompanied Erica to confront the Chandlers. Bianca was in a coma after falling off a terrace while confronting JR about Miranda. Erica and Jack successfully convinced JR to give them Miranda. Erica brought Miranda to Bianca hoping her presence would give her the will to fight. On Christmas Eve, Bianca awoke with Miranda in her arms

2005: Jack almost lost his children to Jonathan Lavery’s terror. Jonathan was poisoning Greenlee. He kidnapped Lily after learning she had witnessed him murder Edmund Grey. After Jonathan seemingly died in a cave explosion, Jack put all his animosity over the Lavery brothers on Ryan.
Jack and Erica’s relationship became estranged over their opposite views on Greenlee and Ryan. Erica called off their wedding.
But Jack was not about to give up after they had gotten so far together. He kidnapped her in a yacht. They made their way to Boca Raton, where all their children were waiting for them.
But even after marrying, their issues remained unresolved. Ryan returned to Pine Valley with Jonathan. Jonathan had undergone brain surgery to remove a behavior altering tumor that caused him to commit his crimes. Kendall revealed she was pregnant with Ryan’s child, Greenlee skipped town. She had Jack file the paperwork for her divorce from Ryan.

2006: Jack worried about Lily’s blossoming relationship with Jonathan. When he caught them together at the Mardi Gras Ball, Jack decided to send Lily back to Boarding School. Lily ran away to New York City, and eloped with Jonathan.
Jack wanted to prove Lily was incompetent in court to annul the marriage. Jonathan saw how traumatic the situation was. He reveled to Jack that he was no longer of a child-like state of mind. He agreed to reveal himself to Lily, if Jack dropped his suit.
Bianca returned to Pine Valley and moved in with Jack. Jack also gained guardianship of his nephew, Sean Montgomery. Sean told Jack about how Barbara had been having problems since Travis’ death. She was now gallivanting about Europe, leaving Sean alone in Seattle.
Erica learned Josh Madden was her son from her first marriage to Dr. Jeff Martin. Jeff came back to Pine Valley to be with his son. Erica moved out of their home and into the Valley Inn where Jeff was also staying. Jackson turned to old friend Brooke for support. Erica misconstrued their friendship for an affair.

2007: When Jack found out about Erica and Jeff’s night together, he retaliated by sleeping with Barbara. Eric and Jack began their divorce proceedings. Erica convinced Jack to star in her new reality show, documenting their divorce. The close quarters of the show actually pulled the couple back together. Behind the camera’s, they had reunited. Erica did not want to loose out on her contract, and made Jack to keep up the charade.
Jack worried about Lily and her relationship with Ava Benton, Denny’s wayward daughter. Adam hired Ava to plant drugs on Sean, so as to have him arrested and kept away from his daughter, Colby Chandler. Jack kicked Ava out of the house for bringing drugs into his home.
Greenlee returned to Pine Valley determined to reclaim the life she had lost. Her desire to reunite with Ryan and claim custody of Spike further estranged Erica and Jackson. On the day their divorce was to be finalized and their ruse revealed, Greenlee and Spike got in a car accident. Greenlee had tried to run away with Spike. The accident left Spike deaf. Unable to come to term with the crisis, Erica and Jackson’s went through with their divorce.
Erica was determined to enact revenge on Greenlee for hurting Kendall and Spike. She falsified Mary’s signature to have Greenlee institutionalized. Before Jackson could confront Erica, Greenlee went missing. She was one on the run for a supposed second attempt to kidnap Spike. Kendall admitted she had framed Greenlee. Greenlee and Zach had been trapped in an abandoned bomb shelter by sociopath Richie Novak. Kendall and Aidan found them, and father and daughter were reunited in time for the holidays.

2008: Jack overheard Aidan and Kendall in an argument. He learned they had slept with each other while searching for Greenlee and Zach. Jackson agreed to let Aidan find a way to tell Greenlee about his infidelity. When Jackson ran into an obviously upset Greenlee at the Hubbard wedding, Jack reached out to his daughter believing she had learned the truth. He was wrong.
Jack stood by Erica as she faced charges for insider trading. US Attorney Samuel Woods had targeted Erica to show his tough stance against celebrities committing crime. While in prison, Erica befriended Carmen Morales. Erica became convinced that Carmen was framed for the robbery she was spending time in prison for. When the women went on the run to exonerate Carmen, Jack followed them. Jack agreed to defend Carmen, and eventually got her released from prison.
When Erica was too released from prison, Jack was surprised to find Erica spending time with Sam. Jack turned his attention to Carmen, whom he had began to share a mild flirtation. Jack and Carmen’s relationship estranged both of them from Erica. After Sam left for the campaign trail, Erica attempted to make Jack jealous by spending time Adam.