The very rich and very spoiled daughter of a famous record producer, Drew Jacobs seemed to have it all...but there was definitely more to the picture. Still carrying a torch for her old flame, Sugar Hill, Drew was determined to get him back when she arrived in Springfield in 1997. The only problem was that he didn't want her. Sugar only had eyes for Dahlia Crede, who was dating Marcus Williams. Although Drew tried to keep Sugar away from Dahlia by threatening to tell her father about their tryst, Sugar merely laughed at her threat and told her to go ahead. However, Drew didn't want to get in her dad's bad side and chickened out. Despite all her attempts at flirting, Sugar wanted nothing to do with her. Having secretly taken pictures of Sugar teaching Dahlia to dance, Drew sent one exceptionally provocative picture to Marcus. Then to arouse Sugar's jealousy, she started publicly flirting with Jesse Blue. Unfortunately, Drew's actions would blow up in her face big time when Sugar found out what Drew had done and told her father and then at the risk of his job, informed Mr. Jacobs that he and Drew had been involved. At that moment, Drew came upon the scene and ended up being berated by her father. After a vicious argument, Mr. Jacobs disowned Drew and financially cut her off. At the same time, Sugar decided to leave Springfield and Drew behind. Forced to support herself, Drew accepted Jesse's advice and began working at Company. Although Jesse, who was dating Michelle Bauer, simply wanted to be friends, it was obvious hat Drew wanted something more. Although Drew tried to lead Michelle to believe that she and Jesse slept together, in the end she confirmed that they hadn't.

Not long after, in 1998, Michelle suddenly left Jesse. Although a heartbroken Jesse tried to find comfort with Drew, she refused to simply be a substitute for Michelle and, this time, shook off his advances. Soon after, Drew was filled with mixed emotions when her father passed away after suffering a heart attack. She was saddened by the loss of the only family she had, but was now able to live a privileged life as the sole benefactor of his fortune. Drew went back to California for his funeral and returned with a new attitude and an agenda; she was going to get the man she wanted on her terms. Drew's first move was to buy a nightclub that she called Millennium. She tried to use the status of the money and her club to win Jesse's affections--even buying him a motorcycle. Unfortunately, her attempts were worthless since Jesse only had eyes for a returned to town Michelle. Seething because of Jesse's bond with Michelle, Drew embarrassed her rival at the Bauer Barbecue when she publicly displayed the nude paintings Jesse had made of Michelle. Although she succeeded in embarrassing Michelle, she also earned Jesse's wrath. Although Drew tried to get in his good graces by buying him an art gallery so he could display his art, she was shocked when he maintained that he didn't want her money. Although Drew begged Jesse to give her another chance to be the woman in his life, he insisted that he was committed to Michelle.

Meanwhile, Mick Santos, whose family was known to be heavily involved in the mafia, worked at the club with Drew. Wanting to make Jesse beholden to her, Drew had Mick draw Jesse into a high stakes poker game. Since Jesse needed money, Drew gave him a loan, thinking he'd lose the money to Mick. Although he ended up winning, Mick assured Drew that it was all part of his plan to set up Jesse for a big fall. The plan seemed to succeed with Mick pressuring Jesse for the money he owed him, forcing Jesse to agree to work at Drew's new club to pay off his debt. However, things started to get dangerous when Mick forced Drew to pay him every week by threatening to tell Jesse about their involvement. Finally, when Drew caught Mick dealing drugs at work, she called the police. An angry Mick confronted Drew and Michelle at the beach. As he began to attack Michelle, Drew hit him over the head with a rock and Michelle broke free. Mick went after Drew and then Michelle hit him again; this time it knocked him out. The two girls took off, only to later learn that Mick had been found dead by the police. They told no one what happened except Jesse and Michelle's best friend, Bill Lewis. Vowing to watch out for each other, the four friends all moved into Drew's apartment above Millennium. Soon after, things got heated when Mick's brother, Danny, showed up in Springfield to find out the real story. After doing some snooping around, Danny came to the conclusion that Jesse was guilty party; Danny suspecte4d that Jesse killed Mick in a fit of jealous rage over Michelle. Fearing that if the truth came out, Michelle's life would be at stake, Jesse decided to take the blame and leave town. Fearing that she would lose the man she had fallen in love with, Drew told Danny that it was Michelle who killed Mick, while conveniently leaving out her part in the crime. Having fallen in love with Michelle, Danny agreed to marry her, in 1999, in order to keep from having to kill her.

Determined to get out of her arranged marriage to Danny, Michelle decided to become an FBI informant and enlisted Drew as her go-between. At the same time, Drew was busy consoling a heartbroken Jesse over the loss of Michelle. After some time, Jesse began to show some interest in her. Reluctantly Drew pushed him away, refusing to play second best. Making matters even more complicated, Michelle was beginning to have true feelings for Danny! Eventually, Michelle decided to make a real go of her marriage. Unfortunately, before she could express her feelings for her husband, Drew had already called the Feds. As Drew agonized over what she'd done, she was shocked to learn that she was adopted. Although she wanted to deny it, Jesse found proof that her father had adopted her. Furious that he went behind her back, Drew sent him away. Later, she went downstairs and began drowning her sorrows in alcohol. At the same time, still devastated by Michelle's betrayal, Danny joined her. The two friends got drunk and ended up in bed together. The next morning, they decided to keep their tryst between them. It didn't take long for Jesse to find out the truth about Drew and Danny. Furious at first, he decided to let it go and asked that Michelle not be told since there was no reason for her to suffer anymore. As Danny and Michelle's marriage broke up, Drew sat back and painfully looked on as Jesse and Michelle got back together. In time, the young lovers realized that things had changed between them. Michelle was in love with Danny and Jesse, to his own surprise, was in love with Drew. After he and Michelle agreed to say good-bye for good, Jesse went to Drew and told her she was the one he wanted to be with. An elated Drew finally had her man.

Finally settling into her life with Jesse, Drew set out on a quest to find her biological parents. In the midst of the search, Jesse found out that Drew's good friend, Selena Davis, was her mother. Selena talked Jesse into keeping her secret. She didn't want Drew to know the truth—that Elena had become pregnant with her while working as a prostitute. Instead, Selena arranged for Drew to think that another woman was her mother...a woman who was already dead. Drew took the bait and went to the cemetery to visit her "mother." When she got there, she ran into Max, the woman's son. Drew was thrilled at the notion that she may have a brother and offered to take Max in. One afternoon, while searching for something in her apartment, Drew found evidence that Selena was actually her mother. When she confronted her, Selena confessed. Furious with her for lying, Drew shut Selena out of her life. In time, however, she came forgive her and accept her in her life. The problem now was Max, who still believed he and Drew had the same mother. Having bonded with Max, Drew decided to keep the truth from him. Making things difficult was Jim Lemay, who saw Max as a troublemaker and disapproved of Max's relationship with his daughter, Susan. Although Jim threatened to call Children Services and report that Drew was not related to Max, he reconsidered. Unfortunately, it was too late, as their conversation was overheard by Max, Hurt and angry, he ran away. Eventually, Max returned to Springfield and made amends with Drew who told him she didn't care that he wasn't her real brother. Drew loved Max and decided to adopt him. Jesse proposed to Drew and the two of them began to plan their future. Only one thing was missing from the scenario: Drew's father. Drew enlisted Selena's help in finding her father.

After some investigating, Selena began to think that there was a possibility that it was the town villain, Ben Warren. Having suffered a severe burn as a child, Ben had a bad scar on his face. He had never been with a woman, so his friends decided to take him to a hooker. He ended up spending the night with Selena and disappeared only to turn up, healed, in Springfield years later. Wanting to confront him about her suspicions before saying anything to her daughter, Selena went to the Santos mansion where Ben was living. When she got there, she fell down a flight of stairs that had actually been rigged to make Ben fall. She ended up paralyzed from the waist down and Drew put off her search for her father to dedicate her time to helping Selena walk again. Meanwhile, Ben was working as Drew's lawyer in her efforts to adopt Max. Growing close to the attorney, she told him about her efforts in trying to find her father and about Selena's past--all they knew was that her father was a scarred college student from Chicago. From that story, Ben figured out the truth--he was her father! After a DNA test confirmed it (a test that Selena's boyfriend Buzz Cooper had tried to alter) Ben revealed the truth to Drew. The two were shocked but thrilled to have each other. With Ben as her lawyer, Drew was able to adopt Max. While celebrating at Towers that night, Drew wondered where her father was. When she didn't get an answer on his phone, she decided to go to his apartment to see what was taking him so long. When she and his brother, Ross, got there, they found him dead from two gunshot wounds. A devastated Drew said a tearful good-bye to her father and vowed revenge on whoever killed him.

Things got worse when Michelle was arrested for the murder. Believing the evidence, Drew turned against her friend and promised to make her pay. Michelle did her best to convince Drew that she was innocent but Drew definitely had doubts. When the story of Mick's murder was brought out in court, Drew was forced to take the stand and admit her part and support Michelle's claim of self-defense. After making her confession, Drew was left worrying about her own safety. Carmen Santos assured her that she wasn't in any danger; she wouldn't seek revenge for Mick because Drew was Ben's daughter. Drew believed her, but, what she didn't know, was that Carmen was the one who killed Ben.

During the trial, in 2000, Michelle finally managed to convince Drew that she was innocent when she convinced her that the eyewitness who supposedly saw her outside Ben's apartment was lying. Unfortunately, the reunion between the two friends would be a brief one. Carmen got to the witness, Ruth, and blackmailed her into lying. When Ruth took the stand and stuck to her original story about seeing Michelle, Drew quickly changed her tune and vowed revenge on her friend. Throughout the trial, Drew's determination to make Michelle pay for killing her father put a huge strain on her relationship with Jesse. Jesse was determined to stick by Michelle and help Danny prove her innocence. His loyalty to his ex-fiancée didn't sit well with Drew and the couple split up. Once Michelle was convicted of the murder, Drew was left without a best friend or a fiancé. Meanwhile, as Michelle was being transferred from the county prison, Danny panicked and begged Jesse to help him. Jesse faked a heart attack to distract the police while Danny and Michelle escaped. When Drew found out about the heart attack she rushed over to the hospital to see Jesse.

Realizing how much he meant to her, Drew asked Jesse to move back in and he accepted. One night while dining at the Springfield Country Club, Jesse decided he couldn't lie to Drew anymore and confessed to faking the heart attack. Drew was furious but realized that she loved him too much to let him go. She agreed to find a way to get past it and sent Jesse to get the car. While she was waiting, she overheard Ross and Blake plan a trip to San Cristobel. Convinced they were going there to help Michelle and Danny, Drew decided to follow and bring her father's killer to justice! Drew revealed the Santos's location to mobsters. Mere days later, Drew learned that Carmen shot Ben. Feeling awful about turning against her best friend, Drew admitted that she told Bernardo Danny and Michelle's whereabouts. In the course of rescuing Danny and Michelle, Jesse was shot but thankfully recovered. Feeling extremely guilty, Drew tried to renew her friendship with Michelle. Though Michelle forgave her, the friendship was somewhat strained.

Not long after, Drew agreed to become partners with Danny in Millennium, despite Jesse's concerns that Danny could return to the mob. That summer, Drew made plans to move to New York with Jesse when he received an art commission. After leaving Millennium in the hands of Michelle and Danny, Drew set out for New York with Jesse and Max.