Jack Snyder came to Oakdale in 1997 to investigate James Stenbeck. After helping to put Stenbeck behind bars, he decided to stay in town and got a job at the Oakdale PD. Jack also got reacquainted with his family and helped his cousin, Holden, in the search for his daughter. Not long after arriving in town, Jack went with Holden to Montana. There he met his Achilles' heel, Carly Tenney. Jack and Carly didn't get along at first; in fact they couldn't stand each other. However, despite all their arguing, there was lots of chemistry between them. Their true feelings for each other became apparent when they investigated arsonist/dirty cop Teague. During the investigation, Jack and Carly got trapped in a cabin where they grew closer and discovered that they had feelings for one another. After returning to Oakdale, Jack wanted to continue the relationship slowly; however Carly was desperate to get married and she dumped Jack to marry Hal Munson.

Reeling from his breakup with Carly, Jack was all set to leave town when he met Julia Lindsey. While helping Julia escape from her controlling fiancé, he fell in love with her. In the meantime, Jack found out the truth about Carly's marriage to Hal--she would inherit a huge trust fund from her sister, Rosanna, if she married a man and had a baby by him by the time the year was out. Disgusted, Jack told Carly to come clean with Hal or he'd completely walk out of her life. In the end, Hal learned the truth himself and divorced her. Luckily for Carly, she got Dr. John Dixon (whom she thought impregnated her with donated sperm) to marry her and, soon after, with the assistance of Jack and Julia, she gave birth to a son, Parker in December of 1998. Soon after, Jack's relationship with Julia ended when he learned that she lied to him about killing David Stenbeck, and also because of interference from Carly. Even though Jack tried to avoid Carly and deny his feelings for her, something about her kept pulling him back. Eventually, long buried feelings rose to the surface and they made love. He dumped Carly again, soon after, when he found out that she lied about her son's paternity, Hal not John was the baby's father.

After a little while though, Jack took pity on Carly and, impressed by how she was trying to turn her life around, befriended her. Jack decided to give Carly another go at their relationship if she could go one month without lying. With Jack's support and understanding, Carly won the bet and Jack proposed to her on Christmas. Unfortunately, Jack was about to get his heart broken yet again. The day of their wedding, Carly arrived at the church and told Jack that she was leaving him to pursue a business opportunity in Paris. A disgusted Jack wrote off Carly forever. Months later, Jack learned that the reason Carly left was because she was being threatened by Winston Lowe, a man she married in Hong Kong. However, by now Jack was married to Julia and decided that he was better off without Carly and her lies anyway.

As much as he wanted to, Jack couldn't deny his feelings and in 2001, after Julia miscarried her and Jack's baby, Jack finally confessed to Julia that he still had feelings for Carly. Though he vowed to stick by Julia, he couldn't stay away from Carly and continued to meet with her. Jack's devotion to Carly drove Julia over the edge and she tried to hurt Carly first by alerting Craig Montgomery that Carly was spying on him and then by killing Carly's prized horse, Flashdance. Jack, concerned about Julia's state of mind, insisted that she check herself into an institution and get help. Though he tried to protect Julia by keeping her crimes from the police, Jack's plan backfired when Julia became increasingly unstable and later went after Carly. Luckily, Jack was able to stop Julia from killing Carly and she was led away by the police. With the nightmare of Julia over, Jack was finally able to be with Carly. Unfortunately, the whole experience with Julia scared Carly and she turned away from him. A few months later, Carly mysteriously disappeared along with Emily Stewart and Rose D'Angelo. Though Barbara Ryan admitted that James kidnapped the women on her behalf, she had no idea as to where they were.

After months of Jack chasing down leads that led nowhere (and after being kidnapped, drugged, assaulted and raped by a demented Julia), James made a deal: he'd return Carly in place of Barbara. Nearly four months after she'd disappeared, Carly was mysteriously released by James Stenbeck and traded for Barbara Ryan. Although elated to be reunited with her family, there was just one problem: due to her treatment at the spa, Carly looked decades older! Disgusted by her appearance, Carly was reluctant let Jack (her rescuer) into her life, and refused to see Craig. However, despite her appearance, all Jack saw was simply the woman he loved. He did not even flinch when he saw her for the first time upon her return; he held her and loved her unconditionally and she felt it. Though afraid that she'd be disfigured for life, the doctor who treated Carly at the spa was captured and "persuaded" by Jack to undo the damage he did to Carly. Her face restored, Carly settled down for a life with Jack. Later that year, Julia returned to town with a baby, Jack Jr., claiming he was Jack's. Though the paternity test confirmed this, later it was discovered that the child belonged to neither Jack nor Julia and was returned to his biological parents.

Unfortunately, Jack's happiness wouldn't last long. Jealous over Carly's friendship and working relationship with Craig, the couple argued bitterly right before their wedding. However, Jack came to his senses and the two reconciled in time for their glorious wedding. Though the marriage started on happy note with Carly expecting their baby, it soured when Jack learned that Carly had a one-night stand the night before the wedding and the child she was carrying might not be his. Bitter, Jack threw Carly out of his house. Despite Holden and Lily's advice, Jack immediately filed for a divorce. Though still jealous of Mike, Jack softened when he finally realized the child could actually be his and he agreed to help Carly in her pregnancy. To that end, when Carly was ordered to avoid stress in order to ensure a safe delivery, Jack demanded that she stop all work at Monte Carlo. Unfortunately, Carly wouldn't listen--especially when she found out Barbara was trying to get her job.. Not long after, Jack suspected that Carly ripped off Barbara's designs and blew up at her. By the time he learned he was mistaken, Carly had disappeared. His concern about Carly's whereabouts turned into fear when he received a report that a dead body was found in the lake. Although the body turned out to be someone else, Jack was still troubled and suspected that Rosanna murdered Carly. After days of gathering evidence against Rosanna, Jack was shocked to learn that Carly had left town voluntarily and was in Montana! After Molly convinced him that Carly wanted him to follow her, Jack hightailed it to Montana where he ended up delivering Carly's daughter, Sage. After promising Carly that he'd stand by her no matter what, Jack remarried Carly in a simple ceremony. Immediately after, Jack learned that Sage was his child.

A year later, Jack would find himself in a perilous situation while trying to protect Carly's cousin Molly. After having helped rescue Molly from a mobster named Starziak who feared she was going to testify against him, Jack offered to let her stay in his house since she had nowhere to go and feared for her life. Molly's fears seemed grounded when Starziak found her at the Snyders and went after her. Fortunately, Jack and Carly arrived home in time and Jack was able to subdue Starziak. However, the frightening ordeal left Molly hysterical and she demanded that Jack take him away. Though proper procedure was to wait for police backup, to appease a hysterical Molly, Jack took the criminal away himself. However, in the car, Starziak attempted an escape by grabbing Jack's steering wheel and the car went into the water! Days later, Jack woke up in a hospital with no memory of who he was. Knowing his name was Jack (from the inscription on his ring), he met a dark haired nurse named Julia Larrabee and was convinced that she was his wife. Julia did nothing to contradict him, and the two bonded. However when he made the assumption that her son, J.J., was theirs, Julia revealed that she'd only gone with his assumptions because his doctor asked her to. Soon after, Jack was released, but had nowhere to stay. Feeling sorry for him, Julia let him stay with her and J.J and promised to help him find out who he was. Jack quickly fell in love with this very sweet woman and her son. Although the search for Jack's identity led nowhere, he and Julia got a clue when a pair of hippies suddenly recognized him from pictures they'd seen from a crazy woman who hitched a ride with them one day, Jack's ex-wife.

Suddenly Jack had a memory flash of Julia trying to kill him! That memory scared Jack and he decided that his former life was better off buried, and he focused on creating a future for himself. While bonding with Julia and JJ, Jack would periodically get flashes of a vivacious blonde but had no idea what those flashes meant. Then came the arrival of Julia's abusive ex-husband, Les, who threatened to take JJ away. Having an instinctive need to protect his new family, Jack talked Julia into marrying him. Although she hesitated since they both had no idea what was in his past, Jack happy in his new life, was falling deeper in love with Julia and assured her that he didn't care about his past. So, after obtaining a fake ID, under the name "Jack Jackson", Jack and Julia married. Weeks later, Jack was startled when Julia suddenly insisted that they had to move immediately. Though Jack was content to remain where he was and worried about JJ leaving in the middle of a school year, Julia insisted that they had to move to Louisville that night. After being told that Julia had a job offer there, Jack agreed to the move. After driving all night, Jack and his new family stopped at a hotel. That night, Jack was shocked to find a police badge in Julia's possessions--his badge with the name Jack Snyder! Shocked, Jack confronted Julia the next morning with the fact that she knew his identity. Julia maintained that she'd only found out the day before when she left the hospital. Buying her explanation that the hospital gave her the rest of Jack's effects, Jack went out and came face to face with a blonde who immediately recognized him--Carly!

Unfortunately, Jack had no memory of Carly at all. Although Carly tried to jog his memory by showing him a family picture and telling him about their past, he still could not remember anything. Not feeling anything for this woman in front of him, Jack only wanted to return to Julia and was shocked when Carly told him that Julia had known who he was, that she'd been to their house in Oakdale. Not knowing who to believe, but not liking Carly's confrontational attitude toward Julia, Jack took Julia aside and demanded the truth. Caught, Julia tearfully confessed that she'd learned of Jack's identity much earlier but kept quiet since she'd fallen in love with him. Touched, Jack forgave Julia. Although Julia wanted to go ahead and move far away, Jack convinced her that he had to find out who he was. So, Jack went back to Oakdale, and brought Julia and JJ, with him. This development didn't sit too well with Carly and she had several run-ins with Julia, whom Carly accused of exploiting Jack's vulnerable state to keep him close. Carly's antagonism toward Julia only ended up alienating herself from Jack.

Knowing that Jack considered Julia his real wife, Carly went to court and had Jack declared incompetent and had him placed in her custody. However, though Jack was now at home, he was colder than ever to Carly. However, he was starting to bond with his children and the Snyder family. After weeks of Jack being hostile towards her, Carly tricked him into going to Montana in an effort to help him remember their past. There Carly discussed their past and started reciting their wedding vows. Suddenly, Jack started remembering them too and his entire memory came flooding back! However, even though his memory had returned, Jack still had a problem--he cared for both women. As Jack struggled with his choice, in the end Carly decided to make it easy for him and signed divorce papers. However, to her delight, Jack had already made his decision and tore them up. Months later, Julia was tragically murdered by her ex-husband, Les, and Jack and Carly were granted guardianship of J.J.

A few months later, Carly started having nightmares of a woman screaming at her demanding to know what she'd done to her child. Convinced this was a traumatic childhood memory, Carly did some digging though her father's things and found a photo of him and a dark haired woman. The odd thing was that the photo was taken near Mabel's in Oakdale. Confused since her father never mentioned living there, Carly asked around but no one remembered her father or the woman he was with. Trying to support her, Jack did some digging and found out who the woman was and her link to Carly. Determined that Carly would never learn the truth, Jack located the woman, Iris, in Oakdale and told her to stay away. Unfortunately, Carly saw them talking. To Jack's relief, Iris simply told Carly that she dated her father when Carly was a girl. Meanwhile, tragedy struck when Rosanna was run off the road by Craig and fell into a coma. At the time of the accident, Rosanna had made plans to adopt a baby boy from teenaged unwed mother. With Rosanna incapacitated, Carly decided to raise her sister's baby, whom she named Rory. Unfortunately the mother, Gwen Norbeck, decided to sue the Snyders for custody since she didn't know or trust Carly. A week later, at the trial, Iris told Carly the secret she'd been hiding—she had given birth to Ray Tenney's child and Carly, in a childhood pique of jealousy, murdered her newborn baby.

Since Carly was underage, the records were sealed. When Carly relayed the story to Jack, he was forced to admit that he'd not only seen the juvenile records—he'd destroyed them. As for Carly, all she remembered was a small baby and Iris screaming that she'd killed him. In the meantime, the custody battle seemed to be turning in Gwen's favor with her getting visitation rights. Desperate to make sure that she didn't lose Rory, Carly set out to make Gwen look like an unfit mother by arranging her to drink tainted water during an outing so Gwen would fall asleep while watching the baby. Upon learning that Carly had arranged for the drugged water, Jack again covered for Carly by lying to Hal. Not long after, Carly and Jack were shocked to learn that Iris was Gwen's mother. Painting herself as the perfect mother, Iris petitioned the court to let Gwen have temporary custody of the baby while under her care. To Carly's dismay, the judge agreed. Later, when Iris accused Will Munson (who was seeing Gwen) of poisoning her, the teens ran off with Rory to New York City. Carly and Jack went to NYC to locate them. Finally they found them. on the steps of the NYC university, Carly and Gwen were on the top steps and Jack, Will and Iris were near the bottom of the steps. Gwen was holding on to the baby carriage, when Carly and her got into fight over Rory, Gwen lost her balance. The carriage went over first, and Jack caught the carriage, and saved Rory, Unfortunately, Gwen lost her balance and fell down the stairs.

Suddenly, at that moment Carly had a memory flash to the night Iris's baby died. She remembered that it wasn't a baby BOY but a GIRL. Carly suddenly put two and two together and figured out that Iris set up Carly in order to get her and her baby away from the Tenneys. That meant that Gwen was her half-sister! In the meantime, Jack manipulated the water vendor's testimony about Carly hiring him to drug Gwen's water during the custody battle. The vendor later told the real story and Jack was found out and suspended. In the end, both women lost when another major revelation came out---Rory was NOT Gwen's baby! He was actually Jennifer Munson's. Unknown to everyone, Craig had switched the babies so everyone thought that Jen's baby had died. With the truth finally discovered, Rory was given to Jennifer and, saddened by Gwen's loss (since it reminded her of her miscarriage of Nora), Carly truly bonded with her sister.

As for Jack, although he was cleared by Internal Affairs for what he'd done, his job had already been given away to Mike's cousin, Nick Kasnoff. He was allowed to work part time on the force, partnered with none other than Nick. Although Carly detested Nick since she felt that he'd stolen Jack's thunder, Jack tried to make the best of the situation, though he wasn't Nick's biggest fan either. Soon, both Nick and Jack were assigned to crack a gambling operation, with Nick as lead detective. Hoping to help Jack get the information to crack the case, Carly (without Jack's knowledge) took a job at the club they were investigating. Despite a few close calls, and several run-ins with Jack, Carly's secret remained safe, although Jack became suspicious of the many conversations between Carly and Nick, who knew Carly's secret. After several weeks of Carly's suspicious behavior, Jack soon learned the entire truth and, feeling betrayed, left Carly. In the meantime, while Jack was finally reinstated at the force, Mike was caught up in trouble of his own when he discovered a skeleton in the basement of the Snyder home (his old house). The body belonged to a woman Mike briefly knew named Maya Gold and since he was the last person to see her alive, he became the prime suspect. However, Carly and Katie Peretti began wondering if it was Nick, not Mike, who was the killer. It turned out the ladies were right.

Realizing he was about to be found out, Nick took both women hostage. Luckily, Mike and Jack found them. Realizing he'd almost lost her, Jack reunited with Carly. Unfortunately, soon after, he was forced to admit that he couldn't fully trust her and their marriage. Angry, Carly threw him out and warned him that she might not wait around for him this time. At the same time, wealthy Simon returned to Oakdale and decided to set up roots by purchasing an old hotel. Hoping to have it renovated, Simon overheard fledgling interior decorator Carly trying to secure a loan. When she was rejected, Simon approached her about working for him. Though Jack objected, due to Simon's questionable past, Carly defiantly ignored his warnings. Unfortunately, Jack wound up being correct—Simon had secured a loan from a loan shark who was demanding payment. Ultimately, he and Carly decided to pull an elaborate jewel heist on Vienna. Though they were successful, Katie (with whom Simon had a one-night stand) became suspicious and blew the whistle on the pair. Carly and Simon then went on the run to evade the police. With Carly gone, an unexpected person would reenter Jack's life—his wayward brother, Brad.

With Carly gone, Jack started to form a close friendship with Katie. Over the course of several weeks, they bonded. Then one day when Katie lamented to Jack about her love life, he unexpectedly kissed her. Though Jack wanted to discuss it, Katie opted to ignore it. As Jack was beginning to look on Katie as more than a friend, so had Brad who told Jack that Katie was becoming close to him. Finally, Katie set the record straight that that was a lie and Jack responded by kissing her. This time, Katie did not ignore it and agreed to go on a date with Jack. As Katie and Jack's relationship was progressing who should show up but Carly. Carly informed Jack that she and Simon were through; she wanted to come back for her kids. At the same time, the jewels of Leonia were returned and the prince decided not to press charges.

However, Jack was far less forgiving and warned Carly that OPD still had her up on charges. He then told her that it might not be a good idea to see the kids since she might end up having to serve jail time. Carly talked him into letting her see the kids and he let them see her at the police station. Though Parker was wary about trusting his mother, JJ pleaded with Jack to help get Carly released. For his kids' sake, Jack took pity on Carly and told her that he could get the DA to drop the charges if she claimed that Simon coerced her. Carly balked about lying at first, then agreed to gain her freedom. At the same time, Katie was convinced that Jack and Carly would reunite. Jack assured Katie that he and Carly were over for good and made love to Katie. As Jack and Carly dealt with how her return affected the kids—especially Parker who was acting out--Katie warned Jack that Carly was plotting to get him back. Jack assured Katie that he would not fall for Carly's tricks. Later, the same night that Carly made a move on Jack, Jack found out about Brad's scheme to ruin things with him and Katie by leading her to believe that Jack was going to propose. Deciding it wasn't a bad idea, Jack did end up asking Katie to marry him. Though he and Carly did bond when they went on to Idaho to rescue a kidnapped J.J.

Jack ultimately chose to stay with Katie. Not only that, but he decided to marry her ASAP. Shortly after the wedding, Jack was shocked to learn that Carly was dying of a neurological disease. Jack strove to make Carly's final days as comfortable as possible and finally he agreed to go with her to Montana. While exchanging fond memories, Carly asked Jack to make love to her one last time. Jack agreed. When he returned home, Jack found that he could not lie to Katie and confessed. Though he tried to explain the lovemaking was merely a way to say goodbye, a disturbed Katie immediately sought an annulment. Later, Jack asked Carly to marry him. Though Carly insisted that she didn't want him to marry her out of some obligation, Jack assured her that he wanted to be with her and pushed for a quick wedding since there wasn't much time left. Finally, on the day of the wedding, standing at the altar, Carly confessed to Jack and everyone in attendance that she was misdiagnosed: she was not dying. Jack was elated at the news; until Rosanna let it slip about Carly mentioning having some good news weeks earlier. It suddenly became to all that Carly had known the truth for weeks, since Montana.

Upset, Jack walked out on Carly and went straight to Katie. Jack begged Katie to take him back but she was stung by his betrayal and refused. Meanwhile, Carly tried to convince Jack that she did what she did out of love, since his actions proved that he still loved her. However, Jack angrily accused her of ruining his life and told her he wished he never had to see her face again. At the same time, Jack learned that Katie intended on having a baby---with Brad! Though Jack tried to make Brad and Katie see that this was a horrible idea, even accusing Katie of doing it just to be close to him, neither listened. In the meantime, Jack was miserable and continually tried to convince Katie to give him another chance. Jack's frustration was obvious to everyone, especially Carly who bore the blame of everything that happened. Jack's attitude didn't improve when he learned that Carly was letting Kit Fowler, the woman whose house JJ was held hostage in, stay at her place. Carly tried to convince Jack that Kit was a good woman who truly wanted to redeem herself but Jack was unconvinced. Not only that, he refused to allow the kids to be at their mother's unless Kit, and her felon boyfriend, Sam, were out. However, instead of doing so, Carly went into business with Kit—purchasing Metro's. It was clear that Carly was trying to put back the pieces of her life but Jack wasn't impressed; he was too overwhelmed with jealousy over Katie and Brad. However, when the grand opening of Metro was a hit, Jack was actually impressed. From that point on, Jack's anger dissipated and Carly regained some of his respect. In the meantime, Jack's jealousy over Katie and Brad finally got the best of him when he kicked down Katie's door when he believed they were having sex---which they weren't. Again, Katie made it perfectly clear to Jack that it was over between them. This time, Jack finally got it through his head that it was over.

Meanwhile, Parker, who Jack officially adopted months earlier, made no secret of his dislike of Sam. Though Parker tried, for weeks, to warn his parents that Sam was a bad man, no one believed him. Desperate to get rid of Sam, Parker robbed Metro and set it up to look as if Sam was responsible. Unfortunately, Parker was exposed very quickly. As the weeks went by, Parker was more and more certain that Sam was a threat but no one believed him. As far as they knew, Sam was merely a ventriloquist who staged shows with his puppet, Cowboy Jack. Parker's attitude toward Sam worried both Carly and Jack and they banded together to help their son. Carly and Jack had Parker resume therapy due to his behavior. Then one night, Parker and Jack went to a hockey game using tickets that mysteriously came from nowhere. Jack suspected they were from Parker's hockey coach but Parker wasn't so sure. Convinced that Carly was in trouble, Parker asked Jack to call her. Carly told Jack she was glad he called but Parker grabbed the phone from Jack before she could elaborate. Though Carly told Parker she was fine, something in her voice told him otherwise. Parker went to Metro just in time to find Sam trying to rape Carly. Parker, having gotten a gun from the Snyder farm, shot Sam and then ran out. Carly chased after him and although Parker wanted to run, Carly convinced him that they had to call Jack.

Later, the pair went to Metro with Jack and by this time Sam was dead. Parker was quickly arrested and, when it was learned that he went to Metro with the gun, the DA called the murder premeditated and charged him as an adult. The fact that Sam had been shot twice did not seem to help. Though Carly insisted that Parker only fired one shot, Margo's questioning so unsettled Parker that he couldn't remember how many shots he fired. Carly and Jack worked together to find a way to clear Parker. To do that, Carly had to be certain about what happened that night. Carly got Jack to return to the scene of the crime and reenact what happened. It worked—-Carly remembered with absolute certainty that Parker only fired one shot. That meant that someone must have come into the bar when Carly and Parker left and finished Sam off.

Jack had the perfect suspect—Kit. Remembering that Kit had been jealous of her and Sam, Carly realized he could be right and the two came up with a plan to trap Kit into confessing. Jack's plan was for them to gaslight Kit by drugging her slightly and then startling her by bringing Cowboy Jack to life. Basically Jack stayed hidden and served as ventriloquist. Unfortunately, that plan backfired as did another effort to try to get Henry to get Kit to confess. Out of options, Carly decided to use herself as bait by flatly telling Kit that she knew Kit killed Sam. Though Jack objected to her putting herself in danger, he agreed since time was running out. Later, Kit called Carly and asked her to meet her at a prop shop in Chicago. Without telling Jack, Carly left to meet with Kit and was almost attacked for her trouble. Luckily, Jack went looking for Carly and found out where she was since her and Kit's conversation was on the answering machine. The pair was now convinced that Kit was their killer. Suddenly, Cowboy Jack dummies kept appearing all over the Snyder house and even in Carly's car. Finding out the dummies were made in the same shop that Kit lured Carly to, Jack and Carly returned to the shop to look for Kit. There they unexpectedly ran into Brad and Katie who were looking for Henry who had been kidnapped. Things came to a head when Kit found Brad and held him at gunpoint. At the point, Jack come up behind to snare Kit. Unfortunately, Kit had attacked Katie earlier and when Katie stumbled upon the scene she distracted Jack. Jack was shot and Carly grabbed his gun to apprehend Kit.

When Kit began firing at Carly, Carly had no choice but to fire back and killed Kit. Jack was rushed to the hospital where his condition remained serious but not critical. Unfortunately, Parker's trial date was drawing perilously near. Carly was determined to clear Parker's name and decided to search for clues herself that would prove that Kit was in Oakdale the night of Sam's murder. Luckily, Carly's determination paid off when she showed Kit's picture to a homeless woman who recognized her. Later, while showing Carly the coat that Kit had given her, the woman found a receipt in the pocket--a receipt that proved that Kit was in Oakdale the night of Sam's murder. Well, not quite since whatever Kit paid for she paid for in cash. Determined to clear Parker, both Carly and Jack tracked down Ruby and convinced her to testify on their son's behalf. Though he was originally found guilty, the verdict was overturned when Ruby testified that Kit told her that she had killed Sam.

During the course of all of this, Jack and Carly had drawn closer, which Carly took as a good sign. Unfortunately, Jack was adamant that they just did not work as a couple and, no matter how hard she tried, Carly could not change his mind. Jack was convinced that they worked better as friends. Things finally came to a head on the night of Katie's engagement party to Brad. That night, Jack wanted to be with Carly. With trepidation, Carly told Jack to only kiss her if he meant it. In response, Jack kissed Carly and the pair made love. The next morning, Jack broke Carly's heart by telling her that nothing had changed.

Not long afterward, Jack was shocked to learn that Brad had a teenage daughter, Liberty, from a one-night stand in high school. A free spirit, much like Brad, Liberty quickly bonded with her father and with Parker. A few weeks after Liberty's arrival, she was joined in Oakdale by her mother, Janet. A free spirit herself, Janet made herself at home in Oakdale and allowed Brad to pay for her room at the Lakeview so she could be near Liberty. Soon, Janet got herself a job at Al's Diner where she met Jack. After a rocky beginning, the two quickly bonded over being the parents of teenagers. Later, Jack and Janet wound up at Yo's bar for 80's night and they enjoyed a fun filled evening dancing in front of Brad and Katie. It didn't take Jack long to figure out that Janet was trying to make Brad jealous and he warned her not to play games with him. Jack made it clear that he liked Janet and suggested that she get Brad out of her system. Soon after, Janet made a play for Brad who rejected her. Afterwards, Jack found Janet at her place in tears and she confided in him about her humiliating rejection.

Their friendship deepened as Jack complimented Janet on what a refreshingly open woman she was. Touched, a few days later, on Independence Day, Janet surprised Jack with a picnic lunch. After a day of Janet following Jack around while he tried to locate missing cameras for WOAK, the pair had the picnic at Janet's place. After dinner, Janet left Jack speechless by asking when the last time he had sex was. Jack made it clear that he wasn't looking for a girlfriend but Janet made it clear that all she wanted was no strings sex. After some prodding by Janet, Jack lowered his guard and the two made love. The following morning they did it again and Jack agreed to Janet's suggestion that they become "friends with benefits."

Soon after, Brad, who objected to Jack sleeping with Janet, stopped paying for Janet's room at the Lakeview. With nowhere to go, Janet was set to leave Oakdale until Jack suggested that she stay at the farm. As time went by, Jack and Janet continued to bond. Meanwhile, Janet hinted at Jack that it might be time to give Parker the sex talk. Though Jack insisted that it was way too early for that, he was proven wrong, mere days later, when told by Janet that Parker and Liberty did the deed. Though Janet, who talked to her daughter about it afterward, assured the Snyders that this was not that big of a deal, both brothers blamed Janet for what happened since she talked to Liberty about sex beforehand and provided Liberty with birth control. After a few heated discussions, the adults eventually formed a united front and told the teens that it might be best if they not see each other for a while—with Brad going to the extreme of hiring a bodyguard. When Liberty slipped out to see Parker, Brad decided he had enough and dragged her off to an impromptu fishing trip without telling anyone. Unfortunately, this freaked out Janet who was concerned about Liberty's whereabouts. When Parker overheard Jack tell her where Brad's car was spotted, Parker sneaked out of the house to greet her. Proclaiming his love for her, Parker tried to convince Liberty to run away with him. Unsettled by Parker's attitude, a worried Liberty told Jack where Parker was. Rattled, Jack questioned his ability as a parent until Janet assured him that he was a great father. As the days went by, Liberty tried to obey her parents and stay away from Parker but he kept seeking her out. Things finally came to a head when Katie and Brad set up Parker to see Liberty on a date with another guy. When they guy they paid, Leo, started getting rough with Liberty, Parker was on hand to save her. After this, the adults permitted Liberty and Parker to see each other under supervision.

Meanwhile, Janet decided that it was time to move out of the farm. Realizing that he'd miss her, Jack suggested that they find a place together. That same day, their relationship hit a rough patch when Carly barged in and announced that Brad dragged Parker to the police station on the accusation of rape. Apparently, Brad and Katie found a dazed Liberty with her clothes ripped. When asked what happened, all Liberty could remember was that Parker was with her. Investigating, Jack discovered that Liberty had eaten drug laced brownies; however, both Brad and Janet accused him of making up the story in order to save Parker. Before the day was over, Liberty finally remembered what happened—it wasn't Parker who went after her, it was Leo. Apparently, he gave her some drug laced brownies and attempted to rape her before she fought him off. Though Janet apologized for accusing Parker, Jack was hurt that she didn't trust him enough. Soon after, an unconscious Leo was found near the reservoir—apparently pulled out of the water by a mysterious person. Leo was taken to Memorial but remained in a coma. Jack questioned the one person who had motive—Brad, but he denied having seen Leo that afternoon. That same day, Katie approached Jack and informed him that Brad lied to him. Brad threw Leo in the reservoir to teach him a lesson but dove in after and resuscitated him when Leo failed to come up out of the water. Janet overheard the conversation and confirmed that when Brad arrived home, he was soaked and wet. Terrified of what kind of trouble he'd be in, Katie pleaded with Jack to help. Jack told Brad that his best bet would be to confess and informed him that if he didn't do it quickly, Jack would be forced to arrest him. That same day, Leo came out of his coma with no memory of what Brad did. Believing that he was in the clear, and not wanting to lose his freedom, Brad decided against confessing and asked Jack to cover for him. Though Jack agreed, the guilt became too much for him and he had a change of heart. When Jack learned that Janet and Brad destroyed the evidence, he briefly resigned from the police force.

Though Jack briefly toyed with the idea reuniting with Carly, it was obvious that he could not get past his issues. Though he admitted that Carly had an emotional hold on him, Jack asked Janet to marry him. Mere weeks later, the pair married in Lily's home. Meanwhile, Parker and Liberty began dating again. Unfortunately, Parker became neglectful of his studies and other responsibilities. When Parker began defiantly acting out, Jack decided to send him away to boarding school using Parker's trust money. Now willing to accept Jack's decision, Parker talked Liberty into marrying him so that he could be legally emancipated from his parents. Though Parker successfully got a judge to marry them by painting Carly a bad mother, Parker was still not guaranteed to get his trust fund. Furious at what Parker had done, Jack angrily threw the newlyweds out into the street. The pair went to Craig who agreed to set them up in a room at the Lakeview. Afterwards, a judge named Craig as the trustee of Parker's trust fund. To Parker's dismay and Jack's surprise, Craig was unwilling to just hand over the money. Craig also successfully planted a wedge in Parker and Liberty's relationship by arranging for an internship in New York City for Liberty. As expected, Parker's jealousy got the best of him and the marriage soon imploded.

Months later, Jack learned that Katie was being held hostage by a mobster Henry was attempting to pay off. Jack raced to the scene and returned fire after being shot at. Jack rushed into the warehouse and was horrified to find Brad lying there. Apparently, the mobster had been using Brad as a shield for cover but since it was so dark, Jack couldn't see him. Tragically, Brad died that day—the same day that his son was born. After finding some old papers of Brad's, Katie named the baby Jacob, after Jack, knowing that was what Brad would have wanted. Guilt-ridden over his part in Brad's death, Jack confessed all to Katie who didn't blame him for Brad's death at all.

Unfortunately, Jack couldn't get past the notion that he'd killed his own brother. Though Janet tried to be supportive, a part of her blamed Jack since she knew he had had two drinks before he went to the warehouse. Believing he had ruined Katie's life, Jack set out to make amends and left town to find one of Katie's ex-husband's in the hopes that Katie would have some happiness. Though Janet agreed to give Jack his space, Carly, who had just returned home after a stint in rehab for her alcohol problem, went in search for him. Desperate for redemption, Jack ended up helping Mike Kasnoff, Molly Conlan, and even foiled Simon Frazier's attempt at an art theft. Jack went on a drinking binge, which abruptly ended when Carly saddled up to the bar for a shot of whiskey. With Carly's encouragement, Jack returned home. However, he couldn't find it in him to stay with Janet and stayed at Carly's instead. At the end of the year, Brad's ghost absolved Jack from guilt by convincing him that Jack was not at fault for his death.

Meanwhile, Jack professed his love to Carly and decided to leave Janet. However, when Jack learned that Liberty had been diagnosed with cancer, he changed his mind and resumed his marriage. Soon after, Curly saw Janet kissing Dusty and tricked Janet's sister into confirming Janet and Dusty's affair. Meanwhile, Janet was desperate for a way to help Liberty and convinced Jack that they had to conceive a child together in the hopes that the child's bone marrow would save Liberty. Learning of Janet's plan, Carly told Jack about Janet and Dusty's affair. Jack decided that he couldn't have a baby with Janet after all and returned to Carly. Not long after, Janet discovered she was pregnant.

Though Jack was still determined to stay with Carly, he was unwilling to cede his role as the father of Janet's unborn child to Dusty. As the months went by, Carly found it difficult to deal with Jack's involvement in Janet's pregnancy. Also causing friction was Carly's involvement in Parker's legal matters. However, in the end, the pair stuck together and Jack ultimately proposed marriage—declaring that it would work this time. Immediately after the wedding, Jack learned that Parker planned to attend the police academy. Though Jack initially objected, everyone else, including Carly, supported the idea. Meanwhile, Janet had her son who turned out to be Dusty's, not Jack's after all. Though Jack was disappointed, he was elated when Carly shared the news that she was pregnant.