Almost immediately following his arrival, Jordan Sinclair would find himself involved in a web of intrigue involving the Ryan family. Jordan arrived in Oakdale to land a prestigious job at Barbara Ryan Originals. Once a successful company, it had fallen on hard times over the years, so wanting to resurrect her now fledging company, its founder, Barbara Ryan, hired the ambition Jordan as her assistant. As a new hire, Jordan quickly earned Barbara's trust and respect, as well as her daughter, Jennifer's. Although Jennifer disliked Jordan at first, it didn't take her long to warm up to him and they formed a very easy friendship. Unfortunately, things would get complicated with the return of Rosanna Cabot, the CEO of Cabot Motors. Jordan's neighbor at the Lakeview, Rosanna warned Jordan that working at BRO could be detrimental to his career, since Barbara's son, Paul, was plotting to oust Barbara from the company and replace her with Barbara's rival, Carly Tenney. Having been told of the bad blood between Paul and Barbara, Jordan became suspicious as to why Paul would want to work for Barbara again and sought out Jen for answers. Although Jennifer trusted her brother, Jordan heeded Rosanna's warnings and remained suspicious of Paul. Things got very complicated when Barbara herself hired Carly. Unable to convince Barbara that she was making a mistake, Jordan soon learned the reason for Barbara's action--she was losing her eyesight. Swearing to keep Barbara's condition from everyone, Jordan supported his new boss and remained wary of her son.

In the meantime, Jordan was continually being befriended by Rosanna. Over the course of a few weeks, Rosanna flirted with Jordan and even kept him from a date with Jennifer. Confused as to Rosanna's interest in him, Jordan was shocked when Paul gave him a dossier on Jordan that he found in Rosanna's apartment--a dossier that she compiled before she even met Jordan. Feeling like a pawn in a game, an angry Jordan confronted Rosanna who told him something startling: soon after losing her adopted son, Cabot, Rosanna was contacted by an unknown person who told her that if she married Jordan, Cabot's birth mother would give him back to Rosanna. Unfortunately, Rosanna wasn't able to give Jordan a reason as to why Jordan was singled out since she was never told. Promising that she'd use all of her resources to find out why he, someone who grew up in an orphanage after his parents were killed in a car wreck, was singled out, Rosanna begged him to marry her to help Cabot. Although an angry Jordan walked out, when he heard her devastating sobs, he relented and agreed to marry her for the sake of her child.

Later, Jordan was shocked to learn that he was Cabot's real father, though he had no memory of who the mother was. Not only that, but Rosanna even wondered whether or not Jordan's job was a lucky break or something arranged by someone else. Although it was becoming apparent that some mysterious person was pulling the strings of Jordan's life, no one had any idea who or what his agenda was. However, all became clear when master criminal James Stenbeck secretly contacted Barbara, his ex-wife. Later, Paul and Barbara came to a sudden realization--Jordan could be James's son! Convinced that he was right, Paul confronted James; at the same time Jordan learned that James was the one who contacted Rosanna and went to confront him. Faced by Paul and Jordan, James was forced to confess the truth--he was Jordan's father. He then proceeded to tell Jordan that he put him in an orphanage because he couldn't care for him, yet he made sure there was someone there to look after him. While Jordan was sickened by this revelation, others in Oakdale were very concerned that James could wind up inserting himself in his son and new grandson's life. While Jordan struggled to distance himself from his new father, he attempted to bond with Cabot, despite opposition from Rosanna.

Meanwhile, Jordan was getting closer to Jennifer while Rosanna was getting closer to Paul; a prospect that scared Barbara since she was afraid of James. Although Barbara tried to interfere in her children's relationships, they both insisted that she back off. Meanwhile, James wasn't about to let his master plan go up in smoke and he put forth another demand--Rosanna and Jordan needed to consummate their marriage. Although Rosanna was willing to do anything for James, Jordan wouldn't. Not long after, James escaped from prison, with help from Barbara, and kidnapped both Rosanna and Cabot. Although Paul came to the rescue, Rosanna knew there was a bomb planted and urged him to get Cabot. Paul didn't and, though he saved Rosanna, Cabot seemingly died in the explosion. In shock, Jordan and Rosanna turned to each other for comfort. Though the pair immediately regretted it, the damage was done for when Jennifer found out she broke things off with Jordan. Despite losing Jennifer, Jordan tried to make a name for himself in Oakdale by joining Lucinda Walsh's corporation, Worldwide. Soon, he found a friend in Lucinda's daughter, Sierra, who had returned to town. Approving of the friendship, Lucinda asked Jordan to keep an eye on her daughter, to keep her away from her ex-husband, Craig. However, Jordan refused to spy on his friend, and when it became apparent that Lucinda was using him in the hopes of keeping Sierra away from Craig, he decided he had enough of being manipulated and left Oakdale to find success in New York.