Isaac Jenkins's sole purpose for staying in Oakdale (or so we thought) was the beautiful Camille Bennett. Though Isaac reluctantly helped Jake McKinnon in his quest to find out about Alec Wallace and verify his wife's death, he wasn't keen on staying in a small town like Oakdale. However, at the airport on Christmas, Isaac met Camille and was instantly smitten with her. When Isaac learned that Oakdale was on the verge of legalizing gambling, he decided he had a lot to gain by staying in town. Isaac was essentially a loner and found it difficult to open up to people. Born to a father who couldn't accept him, Isaac grew up distrustful of people and was determined to make a name for himself.

After floundering in the love department for over a year, Isaac would meet his match in Bonnie McKechnie. Forced to hire the spoiled Bonnie as a favor to Lisa, the pair instantly clashed. Where Bonnie saw herself as above working a common bar, Isaac saw Bonnie as a stuck-up brat. After frequently threatening to fire Bonnie for her condescending attitude and poor work habits, Isaac softened when Bonnie offered to help following the death of his friend Bryant Montgomery. Touched by Bonnie's compassion and willingness to help, he started seeing her in an entirely different light. After dropping their guards and showing each other for who they really were, the pair grew closer and considered dating. Unfortunately by the time they realized their true feelings, Bonnie's former fiancé, the Duke of Glasgow, arrived back into her life. Believing that he couldn't compete with a rich duke, Isaac resigned himself to the fact that he'd lost her. Finally, after some prodding from both Ben and Lisa, Isaac decided to go to Scotland and fight for Bonnie. In Scotland, Isaac warned Bonnie that the Duke was up to something and had ulterior motives for wanting to marry her. Though she was skeptical and married the Ian anyway, the truth came out soon after: the Duke was a fraud and the real heir to the title was Bonnie herself! Shocked, Bonnie accepted the title of Duchess of Glasgow and, pledging her love for Isaac, admitted that her marriage wasn't legal since she hired a fake minister. Now free of Ian and filthy rich, Bonnie left for Oakdale with Isaac.

Unfortunately, the couple's relationship would not be easy due to Bonnie's preoccupation with her mother and the new lawyer in town, the manipulative Marshall Travers. Hating Travers, who was running for the DA position against Jessica, Bonnie set out to make sure he lost by digging up dirt on him. Unfortunately, Bonnie was caught and Jess was forced to concede the election in order for Bonnie to escape punishment. Months later, Bonnie's hatred would intensify when she learned that Marshall raped Jessica! Though he denied the charge at first, he finally realized the magnitude of what he did and apologized. To Bonnie's shock, Jessica accepted the apology and dropped the charges. Angry that Marshall was going scot-free, Bonnie confronted him with a gun and ended up shooting her mother! Given a slap on the wrist (from help by Marshall), Bonnie was sentence to community service. Later, while performing community service, Bonnie became very attached to a teenaged orphan named Sarah. Soon, Bonnie came in conflict with her mother and Isaac since both felt she was giving this girl she hardly knew too much, thus spoiling her. Later, when Sarah was diagnosed with a blood disease that was treatable but expensive, Bonnie decided to adopt her, despite misgivings from Jessica and Isaac. After learning a little of Sarah's history, Bonnie realized something--Sarah could very well be Marshall's presumed dead daughter, Zara! Scared of losing Sarah, Bonnie decided to hide the truth and asked Isaac to marry her so they could be a family and adopt. Though shocked, Isaac agreed. Feeling that Bonnie was devoting most of her energy toward Sarah, he sold Java so that he could devote more time to Bonnie. Soon however, the truth about Sarah came out, and Isaac asked Bonnie if she still wanted to marry him. When Bonnie said no, Isaac realized that their relationship was going nowhere, and he later accepted an offer from a friend of his in Florida and left Oakdale and Bonnie behind.

While in Florida, Isaac apparently received word that Bonnie was jail for accidentally causing Marshall's death. Unbeknownst to Jessica, Isaac and Bonnie corresponded daily and finally he asked her to come to Florida with him as his wife and to bring Sarah. With no misgivings, Bonnie accepted Isaac's proposal and, when she was released, she and Sarah left Oakdale to live in Florida. Unfortunately, it wasn't meant to be. Four years later, Bonnie returned to Oakdale, divorced while Sarah remained with Isaac.