Annie fled New York with her daughter, Emma, to get away from her abusive ex-husband, Terry, with whom she shared custody. She lived in terror, knowing that Terry had an abnormal interest in young girls. When she thought he was breaking into the penthouse, where she was hiding, she shot at him, and shot Ryan instead. She was relieved when Terry finally ended up dead by Jonathan's hand after he attempted to assault Lily Montgomery, and finally began to feel like her life was her own. She remained at Ryan Lavery's penthouse, as the two had become fast friends, and he and her daughter, Emma, were very attached to each other. The two eventually moved into the condo across from Kendall's, and Annie sought Kendall's permission to pursue Ryan romantically.
Ryan found out that he was the father of Annie's daughter, Emma, and insisted that they should start a family together. Ryan proposed marriage to Annie, and she accepted. On Ryan and Annie's wedding day, Ryan's ex-wife, Greenlee Smythe, attempted to stop the wedding, but Kendall locked Greenlee in a shed so Ryan could make it official with Annie. However, it was not official, since Greenlee had Ryan arrested for bigamy. It turned out that Greenlee had never filed the divorce papers. Greenlee divorced Ryan for real, so Ryan was free to marry Annie, which he did.
Annie's life turned upside down when she realized that her brother, Richie Novak, was in Pine Valley and worked at the Comeback as a bartender named "Wes" -- Wes was Richie's middle name. Richie revealed information about Annie's past, including that Annie had given false testimony against him in court. Annie witnessed her father being pushed out of a window; it was revealed Richie had pushed him. Annie's dad was rendered deaf in the fall, and he blamed Annie because he'd never seen the person who pushed him. Annie later testified against Richie in a robbery case and he served seven years in a Chicago prison as a result. Annie later found that her mother had hanged herself after Annie and her mother had argued about Richie being sent to jail based on her false testimony.
Richie was onto Annie's scheme of trying to get pregnant with Ryan's baby behind Ryan's back. Annie realized that Ryan's vasectomy had never been performed, so she could have another child with him. Annie told Ryan that she was pregnant but never told him about the botched vasectomy. When Richie was arrested, he blackmailed Annie into posting his bail, telling her that, if she did not bail him out of jail, he would tell Ryan how she had gotten pregnant behind Ryan's back. Annie bailed Richie out of jail, but Richie did not live to see the end of his trial.
One night, Annie drove in her car, with Richie as a passenger. She got out to fix a tire on her car, and that was when she hit Richie over the head with a tire iron. Richie died, but the initial suspects of his murder were Dre Woods, Colby Chandler, and Cassandra Foster. The three young friends had driven home from a cabin in the woods and rolled over Richie's body. Annie implicated Zach in killing Richie and also staged a car crash to throw the police off her trail.
Annie started to go after Greenlee, since it appeared that Greenlee wanted to get back together with Ryan. Annie almost killed Greenlee when she broke into her apartment. but she did not. Annie's rash and irresponsible actions led her to have a miscarriage. Annie also confessed to Ryan that she had never told him about his vasectomy not happening with his doctor. Ryan went back to Greenlee when he heard Annie's confession.
To get back at Ryan for leaving her, Annie staged a faux kidnapping of Emma with the help of Aidan Devane. She had her friend, Di Henry, look after Emma. Di did not realize it was a staged kidnapping and threatened to kill Annie. However, Annie killed Di. Ryan rescued Emma from a burning church, and Annie was relieved, but she saw that Ryan had known all along that Annie had set up the kidnapping. When Ryan confronted Annie at his penthouse about the staged kidnapping, Annie held a gun on him but then leaped off the balcony.
Annie was next seen at a fundraiser at ConFusion to help the town recover after devastating tornadoes. Annie appeared, wielding a knife and wearing a wedding dress since, in her deluded state, she thought it was her wedding day to Ryan. Annie had stabbed Erica with the knife. Ryan got the knife away from Annie, and Annie was subsequently arrested. At Annie's hearing, she was declared mentally unfit to stand trial, so she was sentenced to treatment at Oak Haven.
Annie's doctor at Oak Haven was Dr. Riley Sinclair. Annie did not realize, at first, that Dr. Sinclair had an agenda regarding her case. Dr. Sinclair was videotaping Annie in her room and managed to have Annie transferred to the maximum-security wing at Oak Haven. Dr. Sinclair did everything in her power to get Annie to confess to killing Richie and proving that Annie could stand trial so she could go to prison. Dr. Sinclair had this motive on her mind because she had been Richie's prison psychiatrist when Richie was in a prison in Illinois. Not only was Dr. Sinclair his psychiatrist but his lover as well. This relationship had caused the warden at the prison to convince Dr. Sinclair to resign, which she did.
Dr. Sinclair got Annie to confess to killing Richie on tape and got the judge to move up Annie's court date so Dr. Sinclair could testify, with her medical expertise, that Annie could stand trial and was faking her insanity. Annie struggled with Dr. Sinclair in one last fight when Dr. Sinclair attempted to inject Annie with poison. Annie fought off Dr. Sinclair, and the doctor was sent to prison. Annie was reassigned a new doctor at Oak Haven, and Aidan promised her he would support her as she got better and healthier.
Aidan held true to his promise to support Annie, even when Annie's imaginary friend, Tori, urged her not to trust Aidan. He researched the real Tori, a friend from Annie's childhood that had died at Annie's birthday party. Richie had killed Tori, but had convinced Annie she had committed the crime. Aidan believed Richie had tortured Annie with the information, which had pushed Annie to kill him. Annie escaped from Oak Haven and made contact with Emma. Aidan went on the run with Annie. When the authorities closed in on them, Annie left Aidan behind and returned to Pine Valley.
Back in Pine Valley, Annie headed straight to Ryan's apartment to see Emma, but Emma was not there. Aidan caught up with her, so she imprisoned him in the basement of Ryan's building and set off to get Emma. Annie found Emma at the Chandler mansion, but she also found a disoriented Adam Chandler. When Adam suffered a heart attack, Annie saved his life and took him to safety in the attic. His twin brother, Stuart, had been murdered that same night.
Adam credited Annie with saving his life, and he repaid her by securing her release from jail. Annie was placed on house arrest, and Adam agreed to have Annie serve her sentence at the Chandler mansion, although it forced Adam to choose between Annie and J.R. The court banned any child from living under the same roof as Annie, so Adam forced J.R. and his son to move out. Many Pine Valley residents questioned Annie's new friendship with Adam, and they accused Annie of Stuart's murder. Kendall Slater was the main suspect, and Adam believed Kendall's family and friends wanted to blame Annie instead of accepting what Kendall had done. He defended Annie against the accusations that she was only after the Chandler wealth and power.
Adam also covered for Annie when she secretly contacted her daughter. When Emma said she had seen Kendall shoot Stuart, Annie used the information to obtain her freedom. The district attorney dropped the charges against Annie in exchange for Emma's eyewitness account of Stuart's murder, but Annie faced another obstacle: retaining Adam's trust. The district attorney provided Adam with a warning about Annie's intentions via Annie's journal. Adam discovered Annie had been planning a wedding to him for months.
Eventually, Adam did propose to Annie, and she gladly accepted. Adam was not fully convinced Annie was innocent, so he set up surveillance cameras to monitor her activities. Annie caught on to the cameras when both J.R. and Scott each flirted with her and kissed her in attempts to prove she did not love Adam. Adam asked Scott to move into the mansion to keep tabs on Annie for him, but Annie used Scott's attraction for her to her advantage, and they became friends. Annie and Emma continued to keep a secret from the night of Stuart's murder, but Emma would not go to the Chandler mansion. She was afraid of Adam.
Zach and Ryan tried to gain Annie's trust, while Scott wondered what Annie was hiding about his father's murder. On the night of the charity dance marathon, Annie was granted a temporary release from her house arrest to attend the event with Adam. She claimed the big secret she and Emma shared was that Emma had accidentally shot Stuart. No one believed her claim, and Emma insisted she had not killed Stuart. Annie regained her freedom when Adam bribed a judge to drop all the charges against her. When Emma fell down the stairs, Annie temporarily moved in with Ryan to be with Emma. Emma reminded Adam that he knew the truth about the murder, and Adam's memory of the evening rushed back -- he remembered accidentally shooting his brother. Adam wanted to confess to the murder, but Annie convinced him otherwise. She told him she was pregnant.
Adam and Annie headed immediately to the altar, but Adam collapsed at the end of the ceremony after the vows had been exchanged. After he recovered, he told Annie he had fought his way back for the sake of their baby. Annie was rushed to the hospital when she faked a miscarriage. Ryan accused Annie of faking a pregnancy, but Dr. Jake Martin confirmed that Annie really was pregnant. Annie was pleased with the news, but Ryan, Zach, and Erica hinted to Adam that the baby could be Scott's. Adam sensed Scott's attraction to his fiancée, and the surveillance camera showed proof of their flirtation, but both Annie and Scott swore the baby was Adam's.
During an argument with Adam over the baby's paternity, Annie suffered a real miscarriage and slipped into a coma. Scott showed Adam proof that Adam was the father of the baby Annie lost, and Adam professed his love to Annie, and then confessed to Stuart's murder. After Adam's profession of love, Annie awoke from her coma and found herself facing charges for covering up Stuart's murder. Adam took the blame for Annie's role, and all the charges against both Annie and Adam were dropped. They celebrated by renewing their vows and taking Ryan to court over custody of Emma. The judge decided upon shared custody.
Adam's family was quick to blame Annie for Adam's next trip to the hospital. He collapsed when Annie performed a seductive dance for him. When Adam recovered, he unveiled his new will, which left Annie as the main benefactor of his estate. Annie was furious when she learned of the strings attached to the inheritance. If she ever became involved with someone else, she would lose everything. Adam claimed he wanted to protect her from someone using her for her money.
The next foe Annie faced was Adam's daughter, Colby. Colby was determined to rid Annie from Adam's life. Colby taped Scott and Annie kissing, but Annie destroyed the footage. Colby's next move was to push Annie to doubt her sanity. Scott realized what Colby was up to and reassured Annie she was sane. Annie began to doubt Adam's devotion to her when an old flame of Adam's, Brooke English, visited. Brooke was there to offer her support when J.R. was near death, due to a rare form of cancer, and needed a bone marrow transplant. Annie was a partial match and was able to save J.R.'s life. Annie used the donation to steer Adam's attention away from Brooke.
Annie was mad Adam rejected her physical advances, and Annie worried when Adam moved Brooke into the mansion. Annie believed she was losing Adam to Brooke, and Adam's children, J.R. and Colby, continued to push Brooke and Adam together. J.R. planned to rid Annie from their lives by proving she did not love Adam and would easily stray from her marriage. J.R. arranged for Annie to accompany him to Washington, DC, to speak about bone marrow donation. J.R. planned to seduce Annie and then reject her, but when the seduction began, J.R. and Annie discovered a surprising passion, and they slept together.
J.R. and Annie intended for their affair to be a one-night stand, and they vowed not to tell anyone when they returned home from Washington, DC. Annie and J.R. fantasized about each other and continued their argumentative banter in front of others. When they were alone, they taunted each other with reminders of their night together. Annie and J.R. gave in to their passion, and Adam walked in on them together. Adam was furious with Annie and J.R., so he left Pine Valley to start a new life with Brooke, the woman he truly loved. Annie was served with divorce papers that listed infidelity as the cause.
Adam arranged for Annie to be removed from the mansion, but Scott invited her to stay with him at the gatehouse. J.R.'s wife, Marissa, found out about the affair. Marissa and J.R. tried to work on their marriage, but Annie kept taunting Marissa about the affair, and Annie continued to flirt with J.R. Scott and J.R. hired Annie to be the head of public relations at Chandler Enterprises, and she convinced Scott to allow her to move back into the mansion for Emma's sake. Annie began to reciprocate Scott's interest in her, but she was still drawn to J.R. Annie and J.R. agreed to stay away from each other so J.R. could save his marriage and Annie could move forward with Scott, but J.R. admitted he cared for her when he rescued Annie from a client's hotel room. J.R. asked Annie to be his mistress. Annie was insulted by J.R.'s offer, so she proposed to Scott and they announced their engagement.
As Scott's fiancée, Annie convinced Scott to move forward with producing the nanotechnology he had illegally obtained from Palmer Cortlandt before Palmer's death. When J.R. learned what Scott had done, Annie went to J.R.'s beach cottage to stop him from turning Scott in to the police. Marissa spotted J.R. and Annie together and assumed she had witnessed a romantic tryst. Marissa told Scott what she believed she had seen. Out of anger and revenge, Marissa and Scott slept together. Afterward, Scott played a voicemail from Annie, which explained why she went to the cottage to see J.R. Even though J.R. had not slept with Annie, Marissa realized she did not trust her husband and filed for divorce.
Marissa told J.R. she had slept with Scott, but Scott did not tell Annie. J.R. was free to be with Annie, but Annie decided to move forward with her plans to marry Scott. Right before the wedding, J.R. made one last plea to Annie to be with him. He told Annie about Scott and Marissa, but Annie married Scott. Annie vowed to forget J.R., but it did not take long for her to end up back in J.R.'s bed. Scott caught them together as the stolen nanotechnology became public. Scott confessed and was sentenced to prison. Scott told Annie to expect divorce papers.
J.R. and Annie were free to be together, except they were not. J.R. was battling Marissa for custody of their son, A.J., and his relationship with Annie could be used against him. Annie and J.R. kept their relationship a secret, but Marissa still suspected they were together. Annie fantasized about becoming J.R.'s wife, but J.R. needed to remind Marissa why she had once loved him so she would drop the custody suit. Annie anticipated an engagement ring from J.R. for Christmas. She was disappointed to receive earrings. J.R. and Marissa spent time as a family with their son over the holidays. Annie sensed J.R. was falling back in love with Marissa, although he swore it was Annie he truly cared about.
Annie began to lose her grip on reality, and she viewed Marissa as a threat to her happiness with J.R. During a conversation with Marissa, Annie began to hallucinate and knocked Marissa out. Annie covered when she claimed a burglar had attacked Marissa. The attack on Marissa pushed J.R. and Marissa closer. Annie began to obsess over J.R., and he pulled back and leaned on Marissa. When J.R. discovered Annie had staged the break-in, he planned to call her psychiatrist. Annie pleaded with J.R. not to send her back to Oak Haven, and she explained why she had threatened Marissa. When Annie discovered Colby had taped Annie's confession to J.R., Annie followed Colby to the beach cottage and handcuffed her to a table. After leaving Colby at the cottage, Annie crashed into an ambulance that was taking Kendall to the hospital for emergency heart surgery.
Annie believed J.R. was going to propose, so she went through his things. Instead of a ring, she discovered papers committing her to Oak Haven for mental treatment. Annie blamed Marissa for planting doubts about Annie's sanity in J.R.'s mind, so Annie tricked Marissa into joining her in the attic. Annie locked Marissa in the attic and started a gas leak. J.R. rescued Marissa in time.
Annie realized her time in Pine Valley as a free woman was running out, so she kidnapped Emma from Ryan and Greenlee's wedding reception. David Hayward and Annie shared a hatred of Ryan and Greenlee, so David assisted her escape. Annie remained on the run with Emma for a few weeks until she was tracked down. J.R. arrived as the team from Oak Haven was preparing to take Annie away. Annie became jubilant when she saw J.R. She believed she was on her way to marry J.R. at a secret wedding.
At Oak Haven, Annie spent time with some other Pine Valley residents, including Janet Dillon and Marion Chandler. They participated in art therapy and yoga sessions together. Annie was thrilled when Erica Kane briefly joined them as a resident of Oak Haven. Erica claimed she had been kidnapped while an imposter took over her life and she had stabbed David Hayward because he had known the truth and done nothing to help her. Erica claimed she was not safe in Oak Haven near Annie because Annie had stabbed her. Annie enjoyed pointing out that Erica had also stabbed someone and they were in Oak Haven for the exact same reason.
Erica's best friend Opal Cortlandt her herself committed to Oak Haven and she devised a plan to break Erica out. Annie overheard their conversation and threatened to tell the guards about their plan unless they took her with when they escaped. The plan was disregarded when Opal was removed from Oak Haven by her son Tad.
Janet set fire to Oak Haven and Annie escaped. She went directly to Ryan's penthouse to visit her daughter. Emma and Annie were overjoyed to see one another and they exchanged hugs and words of love. Ryan allowed Annie to spend some time with Emma and she allowed Ryan to notify the police of her whereabouts. She requested that Emma not be present when the police arrived to take her away. Annie was uncertain where she would be taken since Oak Haven had burned down. Ryan realized Emma needed to know her mother and he agreed to take her to visit Annie at her new facility.