Gilly Grant grew up with her parents in Springfield. A child of the upper middle class, an ambitious Gilly became highly educated, while her brother David ended up in prison. When introduced in May 1989, Gilly was working as a successful producer at WSPR for Holly Lindsey. One of the shows that Gilly produced was the successful TV-show of Johnny Bauer and Chelsea Reardon's called "One on One". Unfortunately, an insane stalker would soon terrorize both Johnny and Chelsea and Gilly herself had to deal with it until the stalker, Rae Rooney, was finally arrested in 1990. On the private front, Gilly flirted with former football player and nightclub owner, Hampton "Hamp" Speakes but they didn't become a couple until months later. Finally in August 1991, Gilly and Hamp became engaged and Hamp's daughter Kat arrived in town to be with her father during the holidays. Gilly did everything possible to befriend Kat but Kat hated her anyway because she was jealous of Gilly and wanted her father to only devote his time to her. Kat schemed to break the couple up. One evening, Gilly prepared a dinner for her, Hamp and Kat but Kat arranged for Gilly's meal to be burned. Gilly realized Kat's scheme and blamed her but Kat denied everything and it lead to problems with Hamp who didn't know whom to believe.

Not long after, Kat and her friend, Bridget Reardon, learned from a police report that Gilly was once arrested for prostitution and Kat tried to blackmail Gilly with it to get her out of Hamp's life. Not one to give in to blackmail, Gilly quickly told Hamp the entire story—that she worked at an escort service for a gigolo when she was younger and was found innocent of prostitution because she didn't know about her boss's dirty work. She also informed Hamp of Kat's blackmail attempt. When an angry Kat ran off after an argument with Hamp and ended up in a car accident, Hamp blamed Gilly and the engagement was called off. Soon after, Kat's mother, Tia, permitted Kat to stay with Hamp for good. Later, Hamp tried to make up with Gilly but she refused because Hamp still believed that she was responsible for Kat's accident. Not long after, Kat and Bridget got into trouble when they stole the police report regarding the accident. When a scared Kat told Gilly everything, Gilly saved her from being charged. From that point on, Kat and Gilly became friends and Gilly and Hamp got back together. In April 1992, Hamp and Gilly were finally able to marry and Hamp arranged for Roberta Fleck to sing their wedding song as a special gift for Gilly.

At the same time, David was released from prison and, although Gilly was glad to see him, she hid him in Hamp's apartment at his request. Two days later, Hamp caught him and though David wanted to leave town to avoid his parents, Gilly and Hamp convinced him to stay. However, what no one knew was that Gilly and David had a dark secret. Meanwhile, one day, David was arrested for stealing Ed Bauer's credit card and Gilly wanted to help him since she felt that she had abandoned him years earlier. Gilly paid his bail and when David was put on probation, Gilly let him stay with her and Hamp despite the fact that David and Hamp didn't like each other. On the professional front, Gilly's boss, Roger Thorpe, wanted Gilly to spy on Ross Marler, who was a candidate for senator. Gilly refused and was later shocked when a reporter offered to sell photos of Ross and his lover, who was none other than Roger's own daughter Blake. Shocked, Gilly bought the photos and wanted to give them Roger. However, she had misgiving and confided in David, who secretly left the photos on Roger's desk. Though Gilly was able to get the photos back, when Roger arrived, she left them, in a panic, on the desk and Roger found them. In the end, Holly ended up publishing the photos to Gilly's dismay. Soon the marriage of Gilly and Hamp became strained because Gilly disapproved of Hamp's contemptuous behavior toward David. In addition, Hamp was upset that Gilly always defended David. Also causing friction was the fact that the ambitious Gilly worked too many hours.

In January 1993, when Holly needed some time off, Gilly convinced her to be her successor during her absence but Roger denied her request. Later, Roger wanted to report on the Spaulding scandal that involved Jenna Bradshaw's father who was reportedly ripped off by Brandon Spaulding. Gilly did the interview without informing Holly. Though Holly learned about it from Henry Chamberlain and wanted to stop it, Roger sided with Gilly and, not only fired Holly, but appointed Gilly as her successor. During the interview, Gilly made Jenna look like a heroine which many people, including Hamp disapproved of. At this time, Gilly was warned against trusting Roger but didn't listen and Roger and Jenna were able to get control of Spaulding Enterprises. Later, Roger asked Gilly to write a damning story about HB Lewis, who was about to get an award from the governor but Gilly refused because Billy Lewis was Hamp's best friend and she didn't want to hurt the Lewises. During HB's party at the Country Club, Roger ordered Gilly to expose the fact that HB had been in prison as a young man. Gilly refused again but Roger had learned about Gilly's past and threatened to tell Hamp about it. Seeing no choice, Gilly was forced to comply. When HB got his award, Gilly confronted him about his prison time and an shamed HB returned the award. At that point, Hamp gave Gilly tn ultimatum: him or her job. Gilly chose her job and Hamp moved out. Depressed, Gilly asked Hamp to return but since she didn't want to tell him the reason for her previous behavior, Hamp refused. Later, Gilly was shocked when Jenna bought Holly's shares of WSPR. Meanwhile, Gilly and Hamp missed each other too much and they finally reunited. In addition, Gilly quit her job at WSPR, knowing that Roger wouldn't hurt her because he no longer needed her.

At this point, Gilly and Hamp wanted to save their marriage but they started arguing again because Hamp accidentally learned that David had gone to jail for killing a gigolo named Davenport. Gilly claimed that David was innocent but Hamp didn't believe her because she refused to tell him who was the real culprit. Not long after, David was wanted for the murder of Vinnie Morrison. He escaped with Kat and a desperate Gilly went to the police and confessed her entire secret to AC Mallet: Six years earlier, when she was in college, Gilly had worked for a gigolo named Miles Davenport, who was owner of a escort service. She was ashamed of the job because Davenport urged his employees to have sex with him. One day, when Gilly and a blonde woman were falsely arrested for prostitution, Gilly confronted Davenport about his crimes. Suddenly, Davenport began to touch and choke her and when Gilly knocked him out with something, she heard two shots. Gilly ran out in panic, whereupon she saw David on the streets. She told him everything and David was ready to take the blame for her because he thought that he wouldn't be charged since he was only 15 years old. Unfortunately, he was charged anyway because his fingerprints were on the gun and though Gilly confessed everything days later, there was no proof and since no one believed her David went to prison. Unfortunately, at this time, the police still believed that she was lying to protect David. Not long after, David returned home but Vivian called the police on him so Gilly helped David to escape again. As for Hamp, he only believed in David's innocence (in the Morrison murder) when Kat returned and confirmed everything. Fed up with Hamp's distrust of David, Gilly decided that there was no hope and ended their marriage. Meanwhile, Gilly, as revenge on Roger, wanted to spy on him for Alan-Michael Spaulding.

In return for her help, Alan-Michael promised her Jenna's half of WSPR shares. Meanwhile, Harley Cooper and Nick investigated the Davenport case and Gilly told them that the blonde woman who had once been arrested with her, Norrie, had never been charged because her boyfriend was a cop and she had simply disappeared. In the meantime, Kat was arrested for helping the fugitive David and Gilly successfully asked Macauley "Mac" West (the cop, who had once worked on the Davenport case and who was the only one who had believed Gilly's version) to become Kat's lawyer. Not long after, Gilly found David in a church. Soon Kat, who blamed Gilly for David's problems, forced Gilly to give her $ 50,000 so that she and David could escape to Canada. Unfortunately, Mac followed Gilly and confessed that he wanted to make up for everything because he had a taped confession of Vinnie's uncle, cop Joe Morrison, in which Joe confessed that he wanted David dead and that he had paid off the witnesses to silence them. Meanwhile, Nick found out Norrie Ryan was the sister of Chief of Police Ryan and that she was Davenport's real murderer. Apparently, Norrie Ryan shot him after Gilly had left him injured because Davenport had once raped her and she had a handicapped daughter from him. After the crime, Mac arrived to find Norrie and wanted to keep an innocent man from going to jail so he destroyed the evidence and let himself be fired by Ryan. Unfortunately, Ryan had David railroaded since his conviction would help him be reelected as chief of police. At this point, Ryan was suspended and, to everyone's happiness, David was cleared of Vinnie's murder because his death was ruled an accident. As for Hamp, he tried to win Gilly back and though she forgave him his behavior toward David, she had changed during the months and realized that she and Hamp were too different and would only argue again due to her career. As a result, Gilly and Hamp parted ways for good.

Meanwhile, Gilly continued her cooperation with Alan-Michael to oust Roger from Spaulding and the key was Brandon's old secretary, Bess Lowell, since she had a document that proved that Jenna had no claim at Spaulding. Unfortunately, Bess was nowhere to be found and during their search for Bess, Gilly and Alan-Michael pretended to be a couple to distract Roger. In the process, Gilly developed feelings for Alan-Michael for real but he only wanted a platonic relationship. Meanwhile, Gilly often arranged for Alan-Michael to peek in Roger's office to find Bess's document but Roger finally realized their game and fired Gilly. When Gilly went on a long vacation, the Spauldings were able to get their company back and when Roger was shot, Gilly became a suspect for a time. Though Alan-Michael planned to give Gilly the half of WPSR as promised, his aunt Alexandra stopped him. In January 1994, Gilly wanted to buy the WSPR shares from Alex but before she was able to present her offer, Alex gave the shares to Nick as a present. Though Gilly explained her deal with Alan-Michael to Nick, he refused to give her half of the station. Later, Gilly made a deal with Nick: she would help him get rid of Roger in exchange of Roger's half of WSPR.

Not long after, Gilly met lawyer Sid Dickerson, who had been her boyfriend in High School. Gilly and Sid became closer again and when Nick and Alex believed that Roger was cooperating with someone named Tashiwa from Hong Kong to get Spaulding back, Gilly wanted to a spy for them in order to get Roger's half of WSPR. The agreement was put in writing. Unfortunately, Roger found the contract. One day, Roger and Holly were arrested for "breaking into the Spaulding mansion" and Gilly saw her chance to get power since criminals were not permitted to head a TV-station. Unfortunately, Alex got the charges against Roger and Holly dropped and this made Gilly so angry that she publicly blasted Alex in a report for wasting taxpayer's resources in a war against her enemies.. Around this time, Gilly and Sid continued to grow closer and made love for the first time, while Sid was briefly jealous of Gilly and Hamp's platonic friendship.

Meanwhile, on New Year 1995, there was a fire at 5th Street and to Gilly's shock, Sid was arrested for arson during a family dinner. Gilly believed in his innocence but to her surprise, Sid did not defend himself, nor would he tell anyone where he had been minutes before the fire started. Thanks to Nick, Sid finally confessed that he had started small fires on 5th Street in order to get clean the area of unwanted criminals. At the time of the fire, Sid was meeting with an informant who was none other than his own brother. This was the reason for his secrecy and, though Nick made Sid a hero in his news story, Sid had to do one year community service for his crimes. As for the big fire, it was accidentally set by teenager Bill Lewis and Sid was cleared of that charge. Afterwards, during a media award show at the Country Club, that Gilly herself moderated, she was honored for her great reporting during the fire and met a well known producer from L.A named Mel. Mel offered Gilly a great future as a TV news anchor in L.A. and Gilly agreed to meet with Mel's bosses because she didn't believe she'd have a bigger career at WSPR. Unfortunately, Sid disapproved of Gilly's plans because he wanted to stay in Springfield. Sid asked Gilly to marry him but she refused. Although they initially argued, they made up and Gilly went to L.A. Gilly ended up accepting the job offer and moved to L.A.. Weeks later, Sid decided to move and build a future in L.A. with Gilly. Unfortunately, Gilly was expectedly fired and returned home. Roger hired her back at WSPR and Sid proposed marriage again.

This time, Gilly accepted the proposal. Meanwhile, Mel confessed to Gilly that someone with influence had arranged her firing and Gilly realized that it was Alan Spaulding because he wanted to keep Sid, his lawyer, in town for a big 5th Street project. When Alan was finally arrested for helping Brent Lawrence evade justice, Gilly was angry that Sid defended him. Later, Mel called Gilly to confirm that it was indeed Alan who was behind her firing and since Sid defended Alan, a hurt Gilly realized that Sid had known the truth for weeks. Finally, Alan's trial began and Gilly realized for the first time how unscrupulous Sid really was. Sid was able to get the charges against Alan dropped due to lack of evidence despite the fact that Alan was guilty. As a result, a disappointed Gilly left Sid and refused to talk to him until Vivian arranged a meeting. However, Gilly wanted nothing to do with him Sid's coldness was finally made clear when David was hurt in an accident at 5th Street and Sid wanted him to sign a document stating that he would not press charges against the responsible company. Later, Sid realized his mistakes and decided to move to Washington to start a political career. Sid asked Gilly to accompany him but Gilly realized that he he still valued his career above all else and let him leave town without her.

Soon after, a frustrated Gilly considered quitting WSPR when Roger's new wife, Dinah Marler, took over but Roger talked her out of it. Not long after, Det. Cutter was murdered and an innocent Marcus Williams was arrested as the prime suspect. Marcus's father was none other than civil rights activist, Griffin Williams. However, her first meeting with Griffin was strained because Gilly wanted to see Marcus's case tried objectively, while Griffin tried to get media attention and get Marcus's release by citing police brutality. Gilly was later surprised to learn that Griffin and Vivian knew each other from the past. In time, Gilly and Griffin started to grow closer and one day in 1996, she heard a conversation in which Vivian demanded that Griffin leave Gilly alone. Gilly was upset with her mother's interference and ignored Vivian's claim that Griffin would only use her for professional opportunities. Later, Charles got Griffin to work at Springfield University and. To Gilly's surprise, Vivian disapproved of this, so Gilly confronted her mother about her antipathy toward Griffin. Vivian was forced to confess that she had had an affair with Griffin while married to Charles and that Griffin had dropped her. Angry, Gilly started to act cold toward Griffin. At the same time, after an unhinged Roger started to blame Gilly for all the problems at WSPR, an upset Gilly quit WSPR for good. Afterwards, she convinced Griffin to let her work for him as his personal assistant. The following day, Griffin seemed to change his mind but when Gilly found a book of Vivian's in his hotel room, she realized that Vivian had interfered again. However, Gilly was able to convince Griffin to hire her.

At this time, Griffin organized protests on 5th Street to save the residents' businesses from Alan and Gilly slowly started to fall in love with Griffin. As for Vivian, she disapproved of Gilly's growing feelings but Gilly silenced her by threatening to tell Charles's about her old affair. Meanwhile, Gilly planned to seduce Griffin but one day, when she arrived at his hotel room, Griffin told her that he already had someone in his room. Later, when Vivian told Charles that Griffin had tried to kiss her, a shocked Gilly realized that Vivian and Griffin had revived their affair. Later, Vivian suddenly confessed that she was a spy for Alan. Later, when Gilly was finally about to seduce Griffin, Vivian burst in and admitted that Gilly was Griffin's daughter! Though Gilly didn't believe her, everyone was surprised when Charles confessed that he had known the truth all along because he had had a blood test done when she was a baby and his blood wasn't been a match. Charles stated that he stayed with Vivian anyway because he loved her and he also loved Gilly and thought that she couldn't be blamed for the mistakes of her mother. Later, Gilly decided to leave town to clear her head. But made it clear to Charles that he would always be her father. The same could not be said for Vivian, who Gilly disowned. After telling Marcus that she regretted not being able to know him better, Gilly left Springfield to travel with David. Later, David returned without his sister, who it was learned had become a successful author.