Assistant District Attorney Doris Wolfe's first high profile case was the Hart Jessup shooting of 1999. Hart had been shot by his spurned wife, Dinah Marler who was on the lam. Knowing that Dinah's mother, Vanessa, knew of Dinah's whereabouts, Doris threatened to charge her with aiding and abetting a felon if she didn't give up Dinah's whereabouts. Though Vanessa remained steadfast, she was released when her ex-husband promised police officer Frank Cooper that he'd get Vanessa to reveal where Dinah was. Unfortunately, even Billy was unsuccessful and Dinah would remain at large for years. That same year, Doris tried her first high profile case---the State vs. Annie Dutton. Under arrest for a variety of crimes, among those impersonating a police officer, Annie had counsel in the form of Ben Warren and the famous Johnnie Cochrane. At the end of the trial, Doris's chief witness, Reva Shayne, surprised Doris by refusing to testify and Annie got off with five years probation and an order to undergo therapy. In 2000, Doris faced off against esteemed lawyer Ross Marler to convict Michelle Bauer Santos for the murder of Ben Warren. Though Pilar Santos stated that her mother killed Ben, Doris had enough evidence to convict Michelle and refused to accept the testimony of the emotionally unstable Pilar. After Michelle went on the run with her husband, Danny, Ross coerced Doris to give him time to prove Michelle's innocence by threatening to tell the press about her suppressing a potentially important witness to protect a reputed mobster—Pilar's mother, Carmen. In the end, Ross convinced the judge to drop the charges against Michelle.

In 2001, Doris went up against the Santos—this time Danny who was on trial for Carmen's murder. Once again, counsel for the defense was Ross Marler The case would get thrown out when it was discovered that Carmen was alive. In 2002, Doris attempted to prosecute Reva for the murder of her brother-in-law, Richard Winslow. That summer, Reva was arrested for disconnecting Richard's life support at Cedars. Seeing that the trial was tearing her family apart, Reva pled guilty and was sentenced to 2 years in prison. However, when Reva's sister, Cassie, produced Richard's living will stating that he not be placed on life sustaining machines, Reva was released. In 2003, Doris was approached by the wealthy Alexandra Spaulding to have her brother, Alan, declared incompetent. However, Alan wandered out of the courthouse before the case went to trial and later the charges were dropped. A few months later, the ambitious Doris was none too happy when the mayor appointed an outsider, Jeffrey O'Neill, as District Attorney. In 2004, Doris found herself. in another high profile case involving the Lewis family when she prosecuted Marah Lewis for the murder of Carrie Caruthers. Since he was romantically involved with Marah, Jeffrey was forced to recuse himself and appoint Doris to handle Marah's case. Doris went after Marah without mercy and Reva was certain that Doris was going after her daughter in retaliation for Reva's having gone free the previous year. When Reva confronted Doris, her interference threatened to make things worse for Marah. In the end, the case was dropped when it was proven that Carrie set up her own shooting.

2006 proved to be Doris's busiest year yet. She started the year attempting to prosecute Reva's son, Jonathan, and niece, Tammy, on arson charges. However, Doris wasn't happy to just paint them as arsonists - she wanted the court to see that they were kissing cousins, as well. To protect Tammy, Jeffrey offered Doris a deal - drop the charges against Tammy, and Doris could have Jeffrey's job. Doris accepted the offer and Tammy was freed, however The People still planned to put Jonathan behind bars. Doris was foiled again when Sandy Foster testified that he was the one who accidentally started the fire. Believing Jonathan to be a juvenile delinquent, Doris was angry when her teenaged daughter, Ashlee began to hang out with him. When Ashlee wound up getting drunk one day, Doris went after Jonathan and had his bar shut down for serving liquor to a minor. Determined to bring down Jonathan, and the entire Lewis family, Doris went after Lewis Construction as well. However, an unexpected person came to Jonathan's aid—Alan. A man with powerful connections, Alan persuaded Doris to drop the charges against Jonathan. That summer, Alan was shot (unknowingly with blanks) and his granddaughter, Lizzie, was arrested for attempted murder. When Doris heard Jonathan tell the police that he gave Lizzie the gun, she was very happy to prosecute him as an accessory to second degree attempted murder. Lizzie tried to convince Doris and Detective Gus Aitoro that Alan is coming after her and her unborn; however, when she tried to show them the surveillance-heavy nursery that Alan had built in the mansion, it was gone.

Not long after, Ashlee called Doris and informed her that she was going on a trip with Jonathan. A furious Doris demanded to speak with Jonathan and accused him of holding her daughter hostage; Jonathan promised to have Ashlee back by next week and then ended the call. Outraged, Doris interrogated Lizzie and Tammy to tell her where Jonathan was but neither girl knew. Just then, Jonathan walked into the police station with Ashlee. When Ashlee defended Jonathan, Doris told her he was just using her. Ashlee replied that this was as much her idea as his. At that point, Jonathan asked Doris how it felt to have someone mess with her child since that was what she was doing by going after Lizzie. Jonathan tried to get her to drop the charges and accused her of having a vendetta against him. At that point, Alan arrived, and arranged for the charges against Lizzie and Jonathan to be dropped. That same year, Doris fired Jeffrey when some scandalous information about his past came to light. In the meantime, Alan began flirting with her in an effort to get her to help him get custody of Lizzie and Jonathan's baby. Doris happily complied and later told his wife that she was looking to "upgrade" her life.

In 2007, Alan found himself implicated in the death of Tammy Winslow from a hit and run driver. Apparently, Alan paid the driver, Mark, Gillespie, to hit Jonathan. Once Gillespie was caught, Doris offered him a deal if he would implicate Alan. Armed with his confession, Doris offered to clear Alan and get rid of Gillespie; for a price she'd name later. That same day, she had Gillespie extradited to Australia on an outstanding warrant and publicly cleared Alan of any wrongdoing. Days later, Doris named her price—a marriage proposal. Faced with the thought of going to jail Alan had no choice but to propose to Doris right there in front of the entire family. Though Alan's wife, Beth, wanted to fight the divorce, she was forced to concede when Doris threatened to prosecute both Alan and Lizzie for Tammy's death. Weeks later, Alan prepared to marry Doris in a lavish ceremony at Towers. After their vows, Cassie (who had been harassing Alan for weeks about his role in Tammy's death) confronted Alan raving about his having taken her daughter away from her. Josh soon followed and got Cassie out of there. Wanting to get away, Alan stepped out. When he returned, he promptly collapsed on Doris. Covered with his blood, Doris and the rest of the crowed were horrified to see that Alan had been shot. He was rushed to Cedars where he remained in a coma for several weeks. In the meantime, after verifying that the wedding ceremony was legally binding, Doris took steps to evict Beth and Lizzie from the mansion. Being led to guest quarters by security, Beth suddenly blurted out that she was pregnant. Though Ashlee was ecstatic, Doris was skeptical and demanded that a pregnancy test be done. Beth refused and walked out, leaving Doris furious and Ashlee confused on what her mother's problem was. Meantime, Doris attempted to exert her control over Ashlee by forcing her to quit her waitressing job at CO2 since she felt it was beneath her. However, Ashlee was later able to get Doris to change her mind.

In the meantime, Josh suddenly confessed to shooting Alan. Though he claimed it was self-defense, Doris had her doubts and warned that he would pay. When Mel suggested that Doris was too close to the case, Doris offered to recuse herself. Later, Doris accepted a deal from Jeffrey—Josh would plead guilty to self-defense and receive a sentence of two years in a minimum security prison. In the meantime, the DA's office rejected the Lewis deal when it was discovered that the bullet that shot Alan was fired from seven feet away; it could not have been self defense. Doris offered a deal of a ten year sentence but Josh refused. Doris had no sympathy for the Lewis family and was upset that Ashlee felt sorry for Josh when she should be supporting the family. Afterwards, a seemingly grieving Doris asked the judge to give Josh the strictest possible sentence and he was sentenced to fifteen years in a maximum security prison. Finally, after being injected with the dangerous drug L-Dopa Alan emerged from his coma. He quickly recovered though claimed to have no knowledge of who shot him. Doris told Alan about Beth's pregnancy and later implied that he'd be getting the Wolfes out of his life. Frantic, Doris rushed to see Ashlee who made a startling confession—she was the one who shot Alan!

A tearful Ashlee confessed that she hated how Alan treated them on her wedding day, and admitted that she was fully prepared to go to prison, However, Doris assured Ashlee that she would protect her since Ashlee was the best person she'd ever known. Alan then approached Doris and informed her that he would keep quiet about Ashlee shooting him; if they get out of his life. Though Ashlee was open to the idea, Doris didn't want to give up everything and decided to take a chance on Ashlee going to trial. However, she backed down when Alan reminded her how it could affect her career if the truth came out. Ashlee's guilt ultimately confessed.. With the help of her attorney, Jeffrey O'Neill, Ashlee was tried as a minor and sentenced to three years in juvenile detention. Several weeks later, Alan presented Doris with a diamond bracelet in exchange for a favor. After telling him she would be wanting more than the bracelet, Doris conceded to Alan's request—having Reva arrested for Lizzie's mysterious kidnapping. Not long after, Doris called in Alan's favor and asked him to fund her mayoral campaign. Meanwhile, Doris finally visited Ashlee in juvenile detention to inform her that she was running for mayor. When Ashlee asked to get out of juvie, Doris stated that it wouldn't look good for her to be released too early. She then revealed that Alan was returning a favor by bankrolling her campaign. The conversation was overheard by Coop who blackmailed Alan to get Ashlee released.

Weeks later, Doris revealed to Ashlee that when became mayor she intended to get rid of CO2 and help implement Alan's plan to remodel the city. In short order Ashlee informed Coop. Not long after, Doris was stunned when Buzz announced that he was running against her. Fearing she would lose a popularity contest, Doris persuaded Ashlee to convince Buzz to drop out of the race. Ashlee was unsuccessful so Doris resorted to smear tactics by attacking Buzz's family during a press conference. Doris even tried to get Buzz to drop out by threatening to dig up dirt on the woman he was dating, nurse Lillian Raines. At the same time, Doris was distressed to learn that Ashlee and Coop were getting closer and she gently warned Ashlee that Coop would never love her. Several weeks later, when the pair finally began dating, Doris asked Coop what he wanted from Ashlee, he assured Doris that he cared deeply for her. However, Doris was convinced that guys like Coop did not go for girls like Ashlee. Meanwhile, Marina Cooper was suddenly kidnapped and Doris wasted no time suggesting to the press that Marina staged the kidnapping herself. Doris's allegation infuriated Frank and he threatened to sue her for slander. Though Buzz tried to take the high road, when Doris continued to discredit his family he got Coop to dig up some dirt on Doris.

In the meantime, Marina was found and Doris immediately had the police detective investigated on charges of improper conduct. Doris brought up Marina's friendship with con man Cyrus Foley and accused her of being in on his charity ball scam, or at the very least keeping quiet about it. Frank was certain that Doris was using this situation for political gain but despite his vehement objections, Marina was stripped of her badge. Afterwards, Ashlee talked to her mother about seeing Coop kiss Ava but worried how Doris would retaliate. Later, Buzz urged Doris to let go control of her daughter, but Doris didn't feel Ashlee was ready for that. Later, Ashlee confronted her mother about arranging a surprise health inspection for CO2 and blasted her for trying to ruin the one good thing in her life. Doris continued to blast the Coopers in the press and did what ever it took to get the political advantage—such as dropping criminal charges for Alexandra Spaulding. In the meantime, Ashlee noticed how extremely confident Doris was about winning the election despite the fact that she was losing in the polls. Doris's attitude raised some flags for Ashlee who did some digging and discovered that Doris had hired a computer hacker to rig the election. Ashlee dismissed the hacker, Einstein, by threatening to expose him and then told Doris what she'd done. Angry at Ashlee's betrayal, Doris vowed that she would win the election fair and square and then destroy the Coopers.

Soon after, Doris entered into a business deal with Bill Lewis. If she won the election, she would green light his plan to renovate Main Street which would include tearing down Company. Finally, Election Day arrived and it looked as if Doris was actually going to win. However, to everyone's shock, a surge of votes went Buzz's way and he won. Doris was devastated. Since she had already stepped down as district attorney, she had nothing. After a few days of sulking, a drunken Doris went to Company ranting about how the Coopers stole the election. When Buzz told her to relax, Doris became outraged and started choking Buzz until Mallet dragged her out and threw her in jail. Later, Buzz shocked Doris by not only refusing to press charges but offering her a job on his administration. Touched, Doris threw herself into her work. Buzz got Doris released from custody and offered her a job with his administration. Later, Buzz and Doris sat down for a meeting with the school board superintendent who wanted to discuss the budget. When he began treating Buzz like a waiter, Doris quickly reminded him that Buzz was the new mayor and he could cut his salary in half if he wanted to. Doris forced the superintendent to pay Buzz respect which impressed Buzz. Days later, Buzz was further impressed with Doris agreed not to block Marina's reinstatement to the force.

In 2008, on the day of his inauguration, Buzz publicly admitted that the election was fixed though didn't reveal who was responsible. As Buzz was arrested, Doris called for a recount and vowed to destroy the Coopers. Ashlee went to the police station and over Buzz's objections confessed to being behind the rigged election. Doris refused to believe that Ashlee was alone in this which Ashlee took to mean that she wasn't smart enough. Ashlee boldly told her mother that she did it to protect the Coopers from her. Though the Coopers urged Doris not to throw the book at her daughter, she insisted that she made a promise to punish whoever was responsible at the fullest extent of the law. Though she pretended not to care, Doris was visibly shaken by what Ashlee had done. Later, Doris came across Ashlee (who thanks to Coop was out on bail) trying to flee and decided to protect her daughter by locking her in her room. Coop came to Ashlee's rescue and pleaded with Doris to let Ashlee make her own choices. When that didn't work, he offered up the name of the person responsible for the Lewis fire—himself. In the end, a humbled Doris declared the fire a tragic accident and, despite her earlier statements, worked to get the charges against Ashlee dropped. Meanwhile, Doris finally realized that Coop did indeed love Ashlee and called a truce with the Cooper family. She then shocked everyone by giving Buzz a job on her administration. Doris's first order of business as mayor was to reappoint Jeffrey as district attorney. Though now a gentler person, Doris was still not immune to Alan's influence and arranged for Rick Bauer to be jailed overnight at his request due to a paternity test switch.

Meanwhile, weeks later Doris was dismayed when a woman lodged a complaint against Frank for unprofessional conduct at a crime scene. (Frank and the woman had flirted) Frank was put on suspension and Doris appointed Mallet to take his place. When Mallet refused, Doris warned him that another person might not be so willing to vacate the position when Frank was cleared. Weeks later, Doris was shocked to learn that Ashlee was at Cedars preparing to have Lap band surgery in order to lose weight. Doris rushed to Cedars to be at Ashlee's side. Though Doris believed that she failed as a mother by not telling Ashlee that she was beautiful enough, Ashlee assured Doris that this surgery was something she really wanted for herself. In the meantime, although Frank was ultimately cleared of any wrong doing, Doris decided to keep Mallet on as permanent police chief. Not long after, Jeffrey launched an investigation of the police department based on suspicion of police corruption. Soon, Dinah Marler presented Doris with two publicity videos she made for Springfield's Mayor – one flattering, the other damaging. Dinah made it very clear that she wanted the investigation dropped. Although Doris tried, Jeffrey continued with the investigation and was shot the day he was set to make a statement to the press. Doris immediately took charge of Jeffrey's cases despite his objections. She also appointed her cousin Chief of Police after Mallet stepped down. Meanwhile, weeks later, Doris consoled Ashlee when she ended her relationship with Coop.

To boost her public image, Doris decided that she had to be tough on crime and concentrated on bringing Rafe Rivera to justice for shooting Jeffrey. Although Jeffrey stated that the shooting was an accident and asked for leniency, Doris was adamant that Rafe be prosecuted. As part of her war against crime, Doris agreed to Daisy Lemay's suggestion for a youth task force in the police department. If Daisy was successful, Rafe's court date would be pushed up. Apparently, Daisy was successful and Rafe was ultimately prosecuted. Weeks after, Ashlee was almost mugged but luckily was saved by Grady Foley. Worried about public perception, Doris decided to get tough on crime again and went after Bill Lewis for the kidnapping of Lizzie Spaulding. At the same time, Ashlee told Doris that Grady needed a job. Knowing that his criminal record was less than stellar, Doris decided that she could use someone like him in as a "problem solver." After catching Grady trying to decipher the code in her book, an impressed Doris was confident that she hired the right man. Meanwhile, on New Year's Eve, Doris was caught in a fire at the evidence warehouse. Luckily, she was rescued by Shayne Lewis. Unfortunately, all evidence against Bill was destroyed in the fire and the case was dismissed.

In 2009, Alan approached Doris about a paper titled "My Two Mommies" that his granddaughter, Emma, wrote which was on the school's website. Seeing a political opportunity, Doris called a press conference and criticized the school for advocating an atmosphere of diversity that might go against some parent's values. Several weeks later, Doris frequented a lesbian bar outside of Springfield and was shocked to come face to face with Olivia Spencer. Doris admitted to Olivia that she had kept her sexual orientation a secret to preserve her career and said that not even Ashlee knew the truth. For her part, Olivia admitted to having romantic feelings for Natalia Rivera. In the meantime, Doris almost found herself in the middle of a groundbreaking case when Jeffrey sued Reva for custody of their unborn child in order to force the child to be delivered early so that Reva could receive treatment for cancer. Though Doris initially reveled in the thought of arguing this career-making case, she backed out when she felt Reva's baby kick. In the midst of this, Phillip Spaulding had returned to town and Olivia demanded that he be locked away. She also blackmailed Doris into pushing up his trial date.

Meanwhile, Doris had become intrigued with Olivia and Natalia Rivera's love story. However, the pair faced two obstacles—Olivia's confusion over her own sexuality and the fact that Natalia was engaged to Frank. Having been asked by Buzz to perform the ceremony, Doris tried to convince Olivia to stop the wedding and tell Natalia that she loved her. Though Olivia refused, Natalia ended up stopping it herself by running out. Several days later, Doris informed Frank that Natalia had feelings for Olivia. Though an angry Frank accused Doris of lying, he later realized that she was correct. At the same time, Frank had been trying to secure a new hearing for Natalia's son, Rafe, so that he could be released early. Deciding that she owed it to Frank, Doris petitioned for a new hearing.

In the meantime, Doris confided in Olivia that she never told Ashlee about her sexual orientation. Not long after, Inspired by Olivia and Natalia's story, Doris finally tried to tell Ashlee the truth but couldn't find the right words. Afterwards, Doris put that situation aside and presided over two weddings and Jeffrey's funeral. Later, upon learning that Ashlee transcribed a book about Jenna Bradshaw, Doris jokingly asked if Ashlee would write a book about her, Ashlee admitted that she didn't even know much about her. Ashlee's words unnerved Doris and after a talk with Buzz, Doris finally revealed to Ashlee that she was a lesbian and had kept it hidden from Ashlee because she was afraid. Hurt that Doris kept such an important piece of who she was hidden from her, Ashlee got upset and ran off. Ashlee quickly forgave her mother though. Later, thanks to some help from Doris, Ashlee was offered a writing fellowship to Berkley University.