Lindsay Rappaport arrived in town in 1998 after her ex-husband, Sam Rappaport, had come to Llanview. Lindsay soon found herself a man, Clint Buchanan. He was on the rebound from Victoria Lord Carpenter. The two of went to Las Vegas together to find Lindsay's son, Will Rappaport and bring him back to Llanview. While Clint and Lindsay were in Las Vegas they got married. Lindsay and Clint's marriage was ruined when Lindsay gave Jessica Buchanan and Cristian Vega money to go elope. Jessica was Clint's daughter and Clint didn't like that at all. They got a divorce. Nora represented Clint in court and Sam represented Lindsay.

After Bo Buchanan and Nora separated, Lindsay started to get very friendly with Bo. She wanted him all to herself, so she changed his DNA test results so it said he couldn't have any children That meant Nora's child, Matthew, was Sam's. That meant Nora had cheated on him with Sam. But then it was found out that Bo's original test was changed by Lindsay, so they did a test to see if Matthew was Sam's kid or Bo's. Lindsay paid a man named Barnes, the lab technician, $500,000 to change the results. The results showed that Matthew was Sam's, but Lindsay was unsure if Barnes ever changed the results. Then Bo's niece, Jessica became pregnant by Lindsay's son, Will. While pregnant, Jessica got hit by Dorian Lord Hayes in a hit-and-run. The baby, Megan, died and Jessica lived, but didn't have her memory. They couldn't find out who did it, and then all the clues started to point to Lindsay. She was soon arrested by Bo, who didn't believe she was guilty. Sam agreed to be Lindsay's lawyer. Lindsay had an alibi, but since it was that she was at the lab changing the test results that night, she couldn't confess to that or she would lose Bo. Lindsay was eventually cleared of the charges when Jessica regained her memory and Dorian decided to confess at exactly the same time.

Lindsay and Bo were about to get married and had made it all the way to the altar when Nora interrupted the ceremony with the information she'd discovered, that Lindsay had tampered with the DNA tests. They went to discuss the situation in private and Lindsay told Bo the truth, and said she was pregnant with his child. But when Bo called the wedding off for good, she lied and said she wasn't pregnant, not wanting him to stay with her only for the sake of the baby. A few weeks later, Lindsay miscarried after having a fight with Nora.

Lindsay found her way to get back at Nora after she was involved in a train wreck and rescued by Colin MacIver, Lindsay's brother-in-law. Lindsay was the first to find out that Nora was still alive, while the rest of her family and friends thought she was dead. Lindsay thought if she could keep Nora out of the way long enough, she would be able to get close to Bo again and marry him. So Lindsay made a deal with Colin to keep Nora a prisoner in return for helping him get back together with his wife, Melanie. When Nora found out about Lindsay's involvement in her kidnapping, Lindsay gave her a memory erasing drug so Nora couldn't incriminate her. Nora eventually made it home safely and was determined to prove Lindsay was involved in her kidnapping. In the meantime, Lindsay paid Colin blackmail money to keep her involvement secret. She got the money from Asa Buchanan, who she blackmailed because she learned he hired the hit man who shot Ben Davidson. Lindsay's son, Will, discovered the secret that she had drugged Nora, and Jen, who had just arrived in town, was upset about her affair with Colin.

Will left town, and Lindsay began to get close to her daughter. Then Jen began seeing Cristian Vega, whom Lindsay thought entirely inappropriate for Jen. When Jen failed to heed her warnings, Lindsay took action. She hired someone to set up a website of Cris parading around in his underwear, and made sure Jen saw it. This broke them up effectively for a time, but Jen eventually found out Lindsay was behind the website and cut her out of her life.

Lindsay tried various methods of getting her back, and decided the only way was to get Cristian out of the picture. She found out Cristian was working undercover to collect evidence against R.J. Gannon. She told R.J. what was going on and an indignant R.J. set a hit man on Cris. Cris broke up with Jen and moved to New York City (to protect her, but Jen didn't know it at the time) and Lindsay and Jen reconciled. Finally, the hit man was put behind bars, and Jen and Cris reunited.

But during Cris' stay in New York, Jen had a one-night stand with Al Holden, which Lindsay gleefully pounced on. She changed the results of Jen's pregnancy test to positive, so she and Al would be forced to have a relationship. Jen found out she wasn't pregnant, but not before Cris and Al had a fight and Al ended up paralyzed from the waist down.

Troy MacIver, Colin's identical twin, fell in love with Nora Buchanan and was determined to get Lindsay to admit that she had drugged Nora so she would pay. So he faked infatuation with Lindsay, but was secretly taping all her conversations, hoping she would confess to drugging Nora. Finally, Troy got engaged to Lindsay, and lured her to the abandoned funhouse outside Llanview. He pretended to be Colin and got her to confess that she had indeed drugged Nora on tape. Lindsay had let it slip that Jen knew about it, too. Lindsay panicked when she heard she was taped and chained Troy to a wheel in the funhouse, demanding she be told where the tape was. Troy never told her: he was eventually rescued by Sam. Nora and Lindsay found the tape just at the same time, and Lindsay threw the tape into the garbage compressor. Nora went into after it and so did Lindsay, and they narrowly escaped with their lives, but Nora ended up with the tape and Lindsay was arrested.

Troy told her she'd better confess or he would tell Jen that Lindsay had changed the results of her pregnancy test, since he had it on tape. Lindsay agreed to confess, as long as Jen would not be forced to testify. Troy agreed not to tell Jen. After a failed attempt to fake insanity, Lindsay was indicted and sentenced to 28 years in prison. While at Statesville, Lindsay became cellmates with Allison Perkins. When Lindsay discovered that Allison's father was the former warden, and that she knew of a secret tunnel that led to the outside, she eventually persuaded Alison to break out with her. Allison soon kidnapped Roxy and Viki, who by this time had reverted to her alternate personality of Niki Smith. Leaving Roxy behind, Allison took Lindsay and Niki to the Buchanan lodge and was preparing to shoot one of them when the police stormed the cabin, along with Viki's husband Ben Davidson. During the rescue attempt, police officer Antonio Vega accidentally shot Ben, which sent him into an irreversible coma. Allison was sent back to St. Ann's, while Lindsay was pardoned by the governor for saving the life of the governor's granddaughter while on the run. But Lindsay's problems were far from over. Trouble with Troy and the evil Mitch Laurence would unhinge Lindsay, who in a fit of jealousy tried to kill Troy! Unfortunately, she fatally shot Sam instead. Weeks later, she confessed, first to Jen, and then to the police. Filled with guilt, Lindsay came unglued and was sent to St. Ann's. Months later, she was deemed fit to be released as an outpatient.

Released, Lindsay sought to lead a quiet, uncomplicated life and fell for D.A. Daniel Colson. Unfortunately, things would get complicated again when Lindsay found herself attracted to a younger man--her former son-in-law, Rex Balsom! Although they tried to fight the attraction, their passions ignited and they began an affair. They were discovered in the end, which damaged not only Lindsay's relationship with Daniel but also her relationship with her daughter.

Once Lindsay and Rex were through, Lindsay tried to focus on running her art gallery. She became much closer to one of her few friends, R.J. Gannon, but Lindsay's world stopped when her daughter Jennifer was found dead of an apparent suicide. Although still devastated by Jen's passing, Lindsay testified at the custody hearing for Jamie Vega, lending R.J. her support.

As Lindsay was recovering from her grief, she told R.J. that she wanted to have a baby with him. He seemed a bit hesitant and never really agreed to anything. R.J. went to visit Nora in the hospital and told her he planned on asking Lindsay to marry him. Lindsay overheard that he was planning to propose and accepted, but it turned out that R.J. was simply saying that to wake Nora out of her coma. When he later proposed for real, Lindsay said no. The two ended up parting ways.

Dorian and Lindsay were there for each other as their romantic relationships fell apart. They ended up teaming up with each other to break up Bo/Paige and Clint/Viki so that they could have the men for themselves. Dorian managed to break Clint and Viki up but Lindsay decided not to break up Bo and Paige and took the high road. Eventually, Paige left the country to join Doctors Without Borders and Lindsay and Bo became closer.

Marcie gave Lindsay a huge shock as she revealed that she nominated her as Llanview's Woman of the Year and that she had won. Unfortunately for her, Nora was the presenter of the award and Lindsay feared that Nora would ruin her night as she had ruined Nora's years ago, when Lindsay had drunkenly revealed Sam and Nora's one night stand and ruined Bo and Nora's marriage. At the award ceremony, Nora played nice and presented the award in a way that honored Lindsay. Tragically, as Lindsay was accepting her award, John McBain arrived and arrested Lindsay for the murder of Spencer Truman.

During her arraignment, Lindsay gave an emotional account of the circumstances and events that led her to kill Spencer. Lindsay then collapsed into a catatonic state. The judge ordered that she be remanded to St. Anne's psychiatric hospital for evaluation. Lindsay awakened from catatonia thanks to a hard slap from Dorian, and began to make progress. After learning of visits from several friends, including Bo and R.J., Nora arranged to have criminal proceedings reconvened, being convinced that Lindsay has been feigning mental illness to avoid prosecution. Once in court, a judge found that Lindsay was insane at the time of the murder. With both Bo and R.J. offering to be her legal guardian, Lindsay returned to St. Anne's sanitarium. Several weeks later, the judge ruled that Bo would become Lindsay's legal guardian, and a delighted Bo and Lindsay headed home together arm in arm.

Lindsay later confided in R.J. that she had indeed faked a breakdown to avoid prosecution for Spencer's murder. From Chicago, R.J. wrote Lindsay a letter thanking her for confiding in him. The letter got mixed up with Nora's papers and in July 2008, in the middle of Lindsay and Bo's wedding, Nora brought up the letter and forced Lindsay to reveal her secret. Bo called off the wedding, and the next day Nora showed up at Lindsay's gallery with the police and had her arrested. At her hearing, after her lawyer failed to get the charges dropped as double jeopardy, Lindsay pled guilty and asked Rex Balsom to "take care of Bo" for her. She was carted off to Statesville Prison.

Bo visited Lindsay in August 2008 after having a surreal experience in which he was seemingly transported back to 1968, just before he was about to ship off to Vietnam, and his mother Olympia looked exactly like Lindsay. Bo told Lindsay he now realized he had spent his entire life reacting to his father, even after Asa had died, and said that was why he had proposed to her. Although he was hurt by Lindsay's latest betrayal, it forced Bo to look at his life and come to terms with who he was. He thanked Lindsay for opening his eyes to that before leaving. Lindsay next appeared as a figment of Rex's imagination in October 2008 as Rex dreamed he was in a game show after being shot and hovering between life and death. In July 2009, as Clint and Nora were about to marry, Bo visited Lindsay at Statesville Prison and said he wanted her to talk him out of stopping the wedding. Lindsay said Bo should stop Clint from marrying Nora if he really loved Nora and could risk hurting his brother, but Bo couldn't bring himself to tell Clint that he was in love with Nora and stood by as Nora and Clint said their vows. In June 2010, Nora and Bo remarried following her divorce from Clint, and Lindsay sent them a wedding gift from behind bars: a license plate she made that read, "Bo&Nora4EVER."

On New Year's Eve 2011, hundreds of inmates escaped Statesville Prison during a major blackout. Lindsay showed up at Bo and Nora's house and told Bo that Troy MacIver was on the loose. Troy had already gotten to Nora and had kidnapped her. Lindsay said she had talked to Troy while in jail and he had claimed that he was going to be together with Nora and Matthew again. Bo had a hunch where Troy had taken Nora and Lindsay insisted on going with Bo. They found Nora and Troy inside a remote cabin, where Troy had once taken a kidnapped Matthew. Troy was about to inject a bound Nora with the same memory erasing drug that Lindsay had given Nora years earlier. Just before he could administer the injection, Lindsay burst into the room and claimed to have just killed Bo. Nora was devastated but then stunned when Bo appeared and tried to get the jump on Troy. The two men fired shots and Troy fell to the ground, wounded. Bo explained that Lindsay had helped rescue Nora, and Nora acknowledged that Lindsay had changed while in prison. Lindsay hoped for an early release from jail, but Nora stopped short, saying only that she would put in a good word for her with the parole board. Bo gave Lindsay the keys to his vehicle and told her to send an ambulance for Troy. Later, Bo was informed that everyone who escaped from Statesville except for Allison Perkins had been apprehended.