Jackson Freemont was brought to Springfield in 1985 by his friend Suzette Saxon to manage the music career of Suzette's newest talent, Lujack Luvonaczek. At this time, Jackson met and fell in love with Lujack's girlfriend, Beth Raines. Jackson befriended Beth and supported her attempts at artwork and although he tried to break Lujack and Beth up, he didn't succeed. About this time, the nefarious Largo Organization (aka Infinity) wanted to take over Sampson Industries and kill Kyle Sampson. Ironically, their logo was the same as the logo that Beth and Jackson had just created for Lujack's music video--a double ring that merge into one another. Later, when Beth identified Bea Reardon's Company guest, Darryl, as Largo, she was kidnapped by the organization onto their tanker. When Lujack made plans to rescue her, Jackson insisted on helping but was kidnapped himself. He and Beth tried to get off the tanker but Largo stopped them and shot Jackson who fell overboard and Beth thought he was dead. Finally the tanker exploded after Kyle, Kurt and Lujack rescued Beth. Unfortunately, the explosion not only killed Largo but also Lujack. After Lujack's death, Jackson turned up alive and comforted Beth. Apparently, Jackson had survived the shooting and swam for help. After learning that Billy Lewis was on trial for the murder of David Preston and for Kyle's attempted murder, Jackson convinced Beth that they had known the truth the whole time. It was David who programmed Billy to kill Kyle using Largo's ring and the logo! After their testimony, Billy was finally cleared of all charges while Suzette confessed to killing David.

In 1986 Jackson and Beth began to work together at Sampson Lewis Oil where Jackson created the Sampson girl contest. After Mindy, who was just married to Kurt Corday, won this contest Jackson became her manager and traveled with her through the country to promote the company. Jackson put forced Mindy to sign a contract forbidding her from becoming pregnant within the next five years. This caused a lot of problems between Mindy and Kurt. After the Sampson Girl campaign fell apart, Jackson once again tried to seduce Beth away from another love: Phillip Spaulding. When Beth rejected her, Jackson spitefully sabotaged her work. Fortunately, thanks to Phillip and Hawk, Jackson was exposed and fired from the company. Later, Jackson comforted a sad Roxie Shayne who just had a big argument with her fiancé Rick Bauer. Jackson and Roxie then had a one-night stand that led to the permanent separation of Rick and Roxie.

In 1987, Warren Andrews turned out to be the murderer of criminal Paul Valère and after kidnapping Jackson, Alan and Chelsea Reardon he was finally arrested. After the legal owner of Warren's nightclub Blue Orchid, left town, she put Jackson in charge of the nightclub. About this time, Jackson became attracted to Chelsea and, seeing both Chelsea's singing talent and beauty, he became her business manager and began to vie with old rival Phillip for her affections. When Chelsea realized that they were fighting an old rivalry for Beth rather than a rivalry for her, she lost interest in both men. Phillip wrote her a letter telling her his true feelings for her, but Jackson intercepted it. Ultimately, Chelsea stayed with Phillip, In the following months Jackson was rarely seen and suddenly disappeared when his mother Lady Agnes came searching for him.

In early 1991, Chelsea received a phone call from Jackson asking her to move to London so that he could support her singing career. Chelsea accepted.