Arrested for driving with alcohol
Embezzled money from the Megan Foundation
Unlawful flight (went on the run with Jessica and Cristian Vega)
Failure to report Colin's death
Will Rappaport was sent to Llanview by his mother, Lindsay, to stay the summer with his parents before he went off to college. On the plane to Chicago, Will met a mystery girl, Roseanne Delgado, with whom he was intrigued. Later, Will discovered that his mother had stayed in Las Vegas to marry Clint Buchanan. Will was introduced to his new brothers and sister, taking a liking to his step-sister Jessica. Being left alone during the day, Will found himself getting Jessica and himself into a lot of trouble, including being arrested by Drew Buchanan. After being locked-up for possession of alcohol, Will's mother told him to find a job.
Will went to see Nora Buchanan, a flame from his daddy's past (unknown to him) and was hired to be a summer intern at her law office. Trying to get him to quit his new job, Lindsay told Will that Nora was the reason for his parent's divorce, but Will soon found out that it was his mother's fling that broke up his lovely home.
One evening Will and Jessica saw Cristian and Roseanne in an embrace. Feeling they were both losing the one they truly loved, they went up to Viki's cabin and got drunk and had unprotected sex. The next morning they could barely remember the event, and Jessica was very sad to have lost her virginity in this way with someone she didn't love. Jessica got pregnant from their night together and Will wanted to proclaim he was the father, but Cristian accepted the responsibility instead. After a few months, the truth came out and the relationships of the four young people involved was never the same again. After contemplating abortion and adoption, Jessica decided to raise her baby and Will was anxious to be a father to the child.
Cristian decided to propose to Jessica and raise the baby together. Jessica accepted and they planned to go to New York together so Cristian could attend art school. At Jessica and Cristian's engagement party at Crossroads, Will and Cris got into an argument and Jessica left and went into labor. As she was walking out into the street, Dorian, who was coming to make amends with Viki, hit Jessica. Afraid of Viki's reaction she called 911 and fled the scene. Jessica ended up in a coma and had a miscarriage. When she came to, she had lost her memory and she didn't remember Cristian and she left town with Will.
Will and Jessica came back to Llanview after a few weeks even though Jessica didn't have her memory back because she had to testify against Will's mother, Lindsay Rappaport, who was on trial for Megan's murder. After she testified, she remembered that Dorian was the one who hit her at the same time that Dorian confessed. With her memory intact, Jessica went to apologize to Cristian, only to find out that he had slept with Roseanne more than once. The wedge between them kept getting bigger and bigger and Will and Roseanne started working together to keep Jessica and Christian apart. Jessica decided she didn't want to go to New York with Cristian and Roseanne went with him instead. At the last minute, Jessica decided she did want to go and Cristian was going to make one more attempt at convincing her, but he ran into Will and Jessica ran into Roseanne and they convinced them that one was happy without the other.
With Cristian out of the way, Will and Jessica started growing closer, bonding over Megan's death. Jessica began sending threatening letters to Dorian and planting tapes of a baby crying in Dorian's house. She ransacked Dorian's house and Will took the blame for it. Then Jessica sent Dorian a note telling her to meet her at Crossroad's where she planned to hit Dorian. Viki found out in time that Will was innocent and they got to Crossroads in time to witness Jessica preparing to hit Dorian. At the last minute she stopped. The whole time Jessica was haunting Dorian she had no idea she was doing it. Cristian had a feeling that Jessica might need him so he went to Llanview that same night, only to see Jessica and Will together. Jessica went to New York to tell Cristian about the haunting but there was miscommunication because Cristian thought she was there to tell him about her and Will and she thought he already knew about the haunting and just didn't care.
Meanwhile, Jessica's grandfather, Asa, didn't want Jessica with a Rappaport (Will), so he called New York to have Cristian's scholarship cancelled in hopes that Cristian would go back to Llanview. But Roseanne called Will, who worked with Asa on the Megan Foundation, and told him that if he wanted to keep Jessica he had better send some money to help them live in NY so Cristian doesn't know that his scholarship is cancelled. So Will has secretly been sending money to Roseanne. On Thanksgiving, Cristian and Roseanne came to town and Roseanne asked Will for $30,000. Will didn't have it so he borrowed it from the foundation. Jessica tried to convince herself that she was happy with Will and they slept together for the first time since Megan.
Cristian and Roseanne went back to NY and Asa finds out that Will stole from the foundation and he(Asa) sent Roseanne a check for $100,000, setting Will up for a big fall. Cristian and Jessica have no idea this money exchange is going on. Cristian and Roseanne go back to Llanview for Christmas and end up at the same hotel as Jessica and Will. Jessica and Cristian talk and they realize there was a miscommunication about the haunting. Meanwhile Will finds out that Roseanne received a check for $100,000 from him, but he didn't send it.
Jessica and Will grew closer and closer as the time went on, but in February of 2000, Bo had to arrest Will for the embezzlement that Asa caused. Jessica didn't want anything to do with him after that. Cristian and Will began to try to dig up evidence on Asa. They succeeded, and after Asa had his heart bypass surgery, Jessica became convinced that Asa set Will up. In March, Jessica went to visit her grandfather while he was recovering in Baltimore and got him to admit on tape how he set Will up. Max caught on to Jessica's plan and Max showed Asa that she had recorded him and Asa threw the tape out the window. Cristian and Jessica went to look for it and found it. On the train to Statesville, Jessica played the tape of Asa's confession to Bo, but both Bo and Nora told her that it would take months to get Will out of jail.
The train crashed and Jessica, Will, and Cristian escaped. Cristian and Jessica hid Will at Viki's cabin until Roseanne discovered them. Soon after that, they quickly went on the run. All during this time Jessica felt guilty about leaving her mother, Viki, while she struggled with breast cancer. Jessica, Cris, and Will all joined a band and Todd Manning caught them all together in Ohio. Soon after that, Todd was able to trick Will and Cris into thinking that Viki was dying so that Jessica could return home, which she did and got arrested. Out on bail, Jessica asked Cris to marry her and he agreed. They were planning their wedding when Jessica found out that Cristian had hid a letter that Will had sent to her. Upset, she broke off her engagement to Cris and went to Ireland to see Will. Thanks to Asa and Max, Will was arrested and sent back to Llanview. He was about to go to jail, when Colin traded the tape that Jessica and Will had made for immunity in Nora's kidnapping case (he had found the tape on Nora after the train wreck). The tape proved that Asa had set Will up and Will was cleared of the charges and set free.
Will and Jessica moved in together into an apartment above Break Bar. They are taking things slowly and have not yet gotten engaged. Will's sister, Jen, recently arrived in town and he has been trying to discourage her from getting involved with Cristian Vega. Will is a suspect in Colin MacIver's murder because the night Colin disappeared, Will had obviously been in a fight with someone and had cuts and bruises on his face. And when Jessica found Colin's body in the woods a few days later, Will convinced her not to tell anyone what they had found. Shortly thereafter, it was revealed that Nora had killed Colin in self-defense and blocked out her crime. Although Will was innocent, the various secrets he'd kept from Jessica took a substantial toll on their relationship. She broke up with him; although he tried to win her back, he conceded defeat after a few weeks and left Llanview. Will briefly returned a year and a half later to bury his father, Sam, and to help his sister Jen cope as they learned that Lindsay had killed their father. After helping his mother find a psychiatric home, Will returned to California.