New District Attorney Jeffrey O'Neill arrived in Springfield in May 2003, and immediately butted heads with Cassie Winslow. A dead ringer for her deceased husband, Richard, an unsympathetic Jeffrey had charges brought up against her daughter, Tammy, when she and friends stole an impounded vehicle and accused Cassie of being a bad mother. Forced to drop the charges due to the fact that the car was not officially impounded, he refused to apologize and continually frustrated Cassie with his abrupt manner. Though not impressed with Cassie, he was impressed with her sister, Reva, when she admitted to having psychic visions; visions that could help him find a serial killer. When Reva refused to help, Jeffrey was left to use more conventional means to catch the killer. While investigating the case, Jeffrey continued to collide with Cassie, whom he found uptight and abrasive. Later Jeffrey ended up saving Cassie's life after one of the murderers (Mitch Hendon who killed his wife, but not the others) attempted suicide by jumping off the Beacon roof. Wanting to stop him, Cassie grabbed him by the arm, only to go over the edge herself. Luckily Jeffrey was on hand to save her. That same night it was revealed that Jeffrey wasn't just a lawyer; he was an agent of the Justice Department. Later as the search for the real killer, Ben Reade, was nearing an end, Jeffrey's real reason for being in town became apparent when he approached Darci Matthews, the girlfriend of Police Chief Frank Cooper, and former girlfriend of employee of mobster Vinnie Salerno, about getting information about Salerno. However, to his chagrin, Darci refused to have anything to do with Salerno, that included helping bring him down.

Meanwhile, Jeffrey finally came face to face with the beautiful Beth Raines and was instantly attracted to her. Not long after, he went to the Spaulding mansion claiming to want to speak with Alan; however his true purpose was to see Beth. Though Beth tried to feign disinterest, it was obvious that she was attracted to him as well, especially when Jeffrey pulled her into a smoldering kiss. Agreeing to go on a date with Jeffrey, he treated to a dinner at a Japanese restaurant where they impulsively made love in a private room! Though this impulsiveness tended to scare Beth, Jeffrey encouraged her to let her hair down and let some spontaneity into her life. Unfortunately Jeffrey's carefree attitude would end up hurting Beth when she saw him leave his room with another woman. Though Jeffrey tried to laugh it off by saying that they weren't exclusive, Beth was hurt and angry and ended their affair.

During his fling with Beth, Jeffrey became involved in the investigation of a Spaulding executive named Brad Green who was suspected of kidnapping or possibly killing his mistress, Lori Jensen. Although he was found to be innocent of harming Lori (who had set up her own disappearance in order to blackmail Brad) Jeffrey still didn't trust Brad and suspected him of being up to something. Knowing that something was going on at Spaulding, Jeffrey kidnapped Harley in order to persuade her to infiltrate and investigate Spaulding for him. Warning Harley that the father of one of her children needed her (namely Phillip Spaulding), Jeffrey convinced her to help him in his investigation. In the meantime, he found himself valiantly trying to fight off the advances of the younger Marah Lewis while he coerced Harley into helping him investigate Spaulding Enterprises. From Thanksgiving (the day that Jeffrey befriended Marah and offered her friendly advice about her feelings toward Sandy) to New Years, Marah shamelessly flirted with Jeffrey. Though he tried to reject her advances, it was obvious that he found her very appealing and finally on New Year's Eve, he caved in to her advances.

In 2004, Jeffrey found himself caught up in the sagas of Antimonius and Maryanne Caruthers when a woman named Carrie Caruthers told him a sordid tale. Apparently over 25 years earlier, a young Alan Spaulding was carousing with four other young men and a young woman named Maryanne. Wanting to have some fun, Alan spiked a pitcher of beer with a Spaulding drug (purchased from the Caruthers family) called Antimonius. That night, out driving, Alan's car went off the bridge. While he and the other men survived, Maryanne perished and her death was covered up. While promising Carrie that he'd look into the matter, Jeffrey sensed she was out for vengeance and learning that she'd been in contact with the young family members of the men involved (most importantly Marah), he warned her to stay away from the girls. At the same time, Jeffrey had been receiving reports of a black market drug called Delirium that was hitting the streets. That drug just happened to be derived from Antimonius. Armed with this information, Believing that Spaulding Enterprises was in league with the mob, Jeffrey recruited Gus Aitoro to infiltrate Spaulding Enterprises and look into the Antimonius situation. As he suspected, shipments of Antimonius were disappearing en route. Things finally came to a head when Carrie was killed and Marah's father, Josh, (one of the men involved in Maryanne's death) confessed. Although Josh tried to paint Carrie as a deranged woman angry because he wouldn't give her a job, Jeffrey knew the real story and had Josh held over for more questioning. Despite some doubts as to Josh's story, Josh was more then willing to take full responsibility for Carrie's death that was until Marah suddenly remembered the events of that night and confessed to the police!

While Marah took responsibly for Carrie's death, Alan stepped up and took responsibility for Maryanne's by accepting a deal with the D.A.-immunity for her death in exchange for Spaulding's files. Meanwhile, knowing that Marah had been taunted, and possibly stalked by Carrie, Jeffrey promised to help her. Unfortunately, when the press got wind that he and Marah had slept together, he was forced to recuse himself from her case and it was handed over to his rival, Doris Wolfe. At the same time, Cassie, through an investigation conducted by Edmund, finally discovered that Jeffrey was a federal agent. Meanwhile, Reva helped close the door on the Carrie Caruthers case when, using her psychic visions, she learned that not only had Carrie faked her death, but had been the one who caused Maryanne's death when she strangled Maryanne, who had washed ashore at the other side of the riverbank.

That April, the sole purpose of Jeffrey's arrival in town was revealed when Danny Santos was elected to mayor. Having backed Danny's run for mayor and even manipulating Cassie into supporting Danny (by telling her she was smart not to), Jeffrey's sole reason for helping Danny get elected became clear when Jeffrey informed Danny that he was a federal agent and he wanted Danny to infiltrate the mob. Although Danny initially refused, Jeffrey blackmailed Danny with faulty "evidence" that the mob funded Danny's campaign. Realizing, he'd been set up, Danny tried to call Jeffrey's bluff to have him arrested, but was forced to comply with Jeffrey's demands when Jeffrey announced that he knew that Danny had used mob money to finance the rebuilding of 5th Street. Faced with Jeffrey's threat that as co-signer of the loan, Cassie could be jailed as well, Danny had no choice but to comply and infiltrate the mob. With Danny in place with mobster Vinnie Salerno and Harley and Gus keeping an eye on Brad Green and the Spauldings, respectively, all the pieces were in place to put an end to the Antimonious smuggling operation. Although the team was able to track a shipment of Antimonious that was delivered to Salerno, the investigation was hampered by Eden, who, under duress by Salerno to get the drug shipment, flushed the evidence down the toilet! With a hit on Eden's head, Jeffrey and Danny had no choice but to fake her death and let her disappear into the Witness Protection Program. Weeks later, Gus and the feds got another chance to nab Salerno and his supplier at Spaulding. Before the sting went down however, Danny informed Jeffrey that Salerno had placed a hit on the DA's head. Seeing that this could work to his advantage, Jeffrey informed Danny to let the hit go down. So, again, Danny faked a hit.

Unfortunately, the operation was almost compromised by Cassie who, seemingly seeing Jeffrey slumped in his car as if he was asleep, went to talk to him just as Danny was pulling the trigger! Luckily, Jeffrey threw Cassie out of the way but was slightly injured in the process. While he was receiving treatment for his injuries by Cassie, she told him what she wanted to tell him in the car--about her suspicions Edmund. Although Cassie spoke of Edmund's getting a package from Brad Green, meeting with Alan Spaulding, and giving a package to Salerno, Jeffrey informed her that it was all circumstantial. Days later, the sting went down and Salerno and Brad Green were nabbed for dealing in drugs.

His job done, Jeffrey made plans to leave town. That all changed however, when he learned from Reva that someone was masquerading as Cassie in Europe. Unsettled, Jeffrey promised Cassie he'd look into it and then called a mysterious person, warning that the imposter better not be her. After trying to convince Cassie that he was trying his best to catch the culprit, Jeffrey went to Europe to confront the suspected imposter. His suspicion was confirmed--it was former Springfield resident (and Cassie's former rival) Dinah Marler. Having pulled Dinah out of a European prison two years earlier, Jeffrey warned Dinah (who was wanted in the U.S. for murder) that he could lock her away again. Far from being concerned, Dinah instead flirted with Jeffrey, bringing to mind when they met two ago--when he recruited her to impersonate Princess Cassie Winslow to his Prince Richard. Thinking he'd frightened Dinah into submission, he learned he was mistaken when Cassie told him she kept getting crank calls asking for 'Blondie." Realizing that Dinah was in Springfield, Jeffrey tried to calm Cassie's fears while at the same time promising to guarantee her safety, and did end up saving her life when Dinah tried to drop a heavy planter on her. As the weeks went by, Jeffrey continued to hunt for Dinah, finally finding her in her brother's apartment. Although he again, tried to threaten her into leaving town, again she broke down his defenses and the pair almost wound up making love.

Soon after, Dinah began actively stalking Cassie. Yet, Jeffrey kept quiet, instead trying to handle Dinah himself and urging her to give up her obsessive vendetta against Cassie. Meanwhile, Jeffrey was confronted by Edmund about why his investigation was taking so long. Although Jeffrey tried to dissuade Edmund from conducting his own investigation into the stalking, it seemed clear that Edmund did not trust Jeffrey or his motives behind helping Cassie. Wanting to prevent Edmund from launching his own investigation, Jeffrey shocked Edmund by telling him exactly what he was expecting to hear--that he was in love with Cassie. As expected, Edmund was rattled and settled down after Jeffrey told him that he had a suspect in custody in Washington. So, to make his lie believable, Jeffrey booked a flight to Washington DC. Unfortunately for him, Cassie decided to join him and confront the imposter herself--leading Jeffrey to have to hire someone to play the imposter. Not long after, the truth would unexpectedly be revealed when Jeffrey was having dinner at the Jessup farm with Cassie and Edmund. When a storm knocked out the electricity, Jeffrey went to the barn to find a generator and was suddenly knocked unconscious. The candle he was holding lit the barn ablaze. Though Edmund was able to drag Jeffrey to safety, unbeknownst to them, Cassie entered the burning barn and spotted RJ trapped at the top level. Cassie became trapped under falling debris, but luckily, Dinah, who had been lurking around the barn, saved the day by rescuing RJ and alerting Edmund and Jeffrey to Cassie's fate.

Now exposed, Dinah was sent to jail where she made no secret of her intention to reveal Jeffrey's secret, unless her charges dropped. The key, of course, was Cassie. As the sole witness to the shooting, if Cassie stated that Dinah was not in sound mind during the shooting--then Dinah would go free. Although he wasn't sure how effective it would be, Jeffrey did try to dissuade Cassie by warning her about how emotionally grueling a long trial would be. Later, when Jeffrey tried to persuade Dinah that they should run away together, she suspected that his sole motivation was to get her far away from Cassie and refused his offer. Although, Jeffrey vowed to prosecute her to the fullest despite her threats to reveal his secrets, his previous warnings to Cassie had an effect and she made a statement that Hart's shooting was an accident. Thanks to that statement, Dinah was a free woman. On the day of Dinah's release, Edmund and Jeffrey were rattled to learn that she did not get picked up by her father, she went in another car. Suspecting that something was seriously wrong, they tried to contact Cassie, but to no avail. So both men assumed that Dinah must have kidnapped Cassie. The two men soon tracked the car to Laurel Falls where they were shocked to discover that Cassie wasn't the one in danger--she was holding a gun on Dinah! Thanks to some words from Edmund and some reverse psychology from Jeffrey (who told Cassie to shoot Dinah), Cassie decided to spare Dinah's life. Meanwhile, a little later, Reva learned that the young man (Sandy Foster) she thought was her long lost son was actually an imposter and asked for Jeffrey's help in finding out what happened to her real son, since she suspected foul play.

Just as he began his investigation, Jeffrey received a visit from his boss from Washington who rewarded Jeffrey with a cushy position in Paris, a reward for his work on the Salerno case. However, Jeffrey, wanting to help Reva, decided to resign in order to remain in Springfield. Months later, in a moment of loneliness, Jeffrey let himself be seduced by Dinah. However, he soon discovered she had an ulterior motive when he discovered that she'd poked holes in his condom. Realizing this was all about getting pregnant so she could have a life like Cassie's, Jeffrey blasted Dinah and threw her out. Although Dinah initially taunted him by implying that she was pregnant, she later let him off the hook by admitting that she wasn't. Then on New Year's Eve, Jeffrey learned from RJ why he was knocked out the night of the fire--Edmund hit him over the head! Learning RJ got the news from Dinah, Jeffrey went to Dinah for confirmation. She confirmed that she saw it happen and tried to encourage him to go to Cassie with what he'd learned. Jeffrey left, but instead of finding Cassie, he found Edmund whose guilty reaction upon being confronted confirmed what Dinah had just told him.

Although conflicted as to whether to tell Cassie, Jeffrey ultimately kept quiet and even helped a distraught Cassie go through with her wedding in 2005. Jeffrey even ended up performing the ceremony when the pastor left because Cassie was so late. As Jeffrey was dealing with his growing feelings for Cassie, professionally he had the unenviable job of prosecuting Harley for Phillip's murder. Knowing that Phillip's behavior probably drove Harley (who had no memory of the murder) over the edge; Jeffrey tried to help her by offering a plea bargain: if she pled guilty to manslaughter she'd get a lesser sentence than if she was convicted of murder. Unfortunately for Harley, her lawyer, Gus, continually advised her not to take the deal. He also found himself dealing, again, with a jealous Edmund who confronted Jeffrey about secretly giving Cassie flowers. Having no idea what Edmund was talking about since he never sent flowers, Jeffrey advised Edmund to trust Cassie. Later, he advised an upset Cassie to stop keeping secrets from her husband. Meanwhile, the same day that Harley unexpectedly agreed to the plea bargain, Reva informed him that she knew that Edmund caused the fire at the Jessup farm months earlier and wanted to bring up charges. Jeffrey agreed to draw up the papers but asked Reva to sleep on it, warning her that if she dropped this bomb, Cassie may never forgive her. A day later, Cassie discovered the truth and confronted Jeffrey who was forced to confirm it. Although he urged her to talk things out with her husband, a confused and angry Cassie wasn't sure that she could.

Meanwhile, Jeffrey and Cassie continued to bond. Distraught over Harley going to prison Jeffrey continued to find company in Cassie who informed him that she was separating from Edmund. The pair grew even closer and kissed but both pulled away before it went any further. Later, the pair nearly make love but Cassie stopped herself, not wanting to use Jeffrey to get back at Edmund. But by this point, Jeffrey could no longer deny his feelings and made it clear to Cassie that he had feelings for her. Later, Jeffrey and Cassie were both shocked when in an effort to get Cassie back, Edmund arranged for Dinah to carry their baby! Although the baby was legally Cassie and Edmund's (Cassie and Edmund had gone to a fertility specialist several weeks prior), Jeffrey warned Cassie that Dinah wouldn't give up the baby so easily. Later, Jeffrey lent a hand trying to help Cassie keep custody of her son, Will, when the father, Alonzo, insisted the boy be sent back to San Cristobel to begin his education. Knowing that Cassie, Edmund, and Dinah were all going to San Cristobel so Cassie could talk to Alonzo, Jeffrey followed and ultimately paved the way for Cassie to speak with him. In the end, Cassie decided perhaps it was best for Will to be educated in San Cristobel after all. Sympathetic, Jeffrey told Cassie that he was going to bow out and give Cassie and Edmund the chance to be happy. Dinah on the other hand was far from willing to let the Winslows persevere and tried to get him to attend a party in Cassie's honor.

Although he tried to take the high road, Jeffrey couldn't resist and at the party, told Reva that he intended to tell Cassie he loved her. Although Reva succeeded in talking him out of it, Cassie's world was ripped apart that night when she learned that Edmund arranged for Dinah to be kidnapped and witnessed him try to harm her (both set ups by Dinah) Devastated, Cassie wrote Edmund off for good and ran to Jeffrey's where they shared a passionate kiss. Although Cassie insisted it was over between her and Edmund, Jeffrey wasn't sure he wanted to be her rebound. However, his desire for her won out and the pair finally made love. Days later, Jeffrey was unsettled when Cassie referred to him as "Richard" and to prove herself to him, Cassie allowed herself to be blindfolded and the two shared a romantic moment. Although Cassie had some trepidation about going out in public, they overcame their fears and were both relieved when Tammy gave her blessing about their relationship. Not long after, Cassie got an ultimatum from Edmund--break up with Jeffrey or be removed from the baby's life. Though Cassie tried avoiding Jeffrey, soon they decided that Edmund couldn't bully them since they could easily have Dinah against Edmund for kidnapping. Weeks later, though, Dinah recanted her story and confessed that she'd never been kidnapped. Though they lost their leverage, the couple refused to let Edmund dictate to them.

Finally, one night, Edmund presented Cassie with a beautiful baby girl whom she named Hope. According to Edmund, Dinah had suddenly gone into labor at the barn and immediately after giving birth left town. A few days later, while getting medicine at Cedars, Jeffrey ran into Edmund and noticed that Edmund was carrying a prescription under Dinah's name since Dinah had gone out of town. Edmund then informed Jeffrey that he had a drug problem. Jeffrey intended for Edmund to confess his addiction to Cassie, however circumstances prevented it. Edmund then tried to get rid of Jeffrey by anonymously sending him messages stating that the people he cared about were in danger. To keep Cassie and Hope safe, he tried to keep his distance to Cassie's dismay. He then enlisted Ross's help in bringing the criminals to justice, while at the same time pledging to help Ross find Dinah, believing her to be somewhere in Europe. Several days later, Jeffrey learned that Edmund himself was behind the threats. In the meantime, fledgling police officer Marina was suspicious about the circumstances surrounding Michelle losing her newborn child after a car crash, and after some investigating finally informed Jeffrey of her suspicions--that Edmund switched babies: that Hope was Michelle's baby, not Cassie's! Though doubtful, he agreed to get some DNA from Hope so they could test her and know for sure. The day of the christening, Jeffrey was unsettled to learn that Marina was right--Hope was not Cassie's daughter. That evening, Jeffrey had the sad duty of breaking the news to Cassie. Although she refused to believe it at first, when he showed her the DNA test she was forced to accept the sad truth.

Though Edmund denied everything, Jeffrey wasn't just going to take Edmund's word for it and had a test done. Since Michelle was out of town, Jeffrey used her comb from her locker at Cedars.. He and Cassie were relieved to learn Michelle was not a match to Hope. Mere days later, Dinah suddenly reappeared and returned Hope to her rightful father--Danny. Apparently, Edmund had stolen Michelle's baby after her car accident. Although Jeffrey tried to tell Danny about the recent DNA test, Danny didn't exactly trust Jeffrey's word and demanded another test be done. Sadly, it turned out the recent test was false---Hope was in fact Danny and Michelle's daughter. Later, Edmund tried to convince Jeffrey that Dinah was the mastermind behind the baby switch but Jeffrey didn't believe it and Edmund was then sent to jail. Later, Edmund escaped from prison and forced Cassie to flee with him to San Cristobel. Fortunately, she cleverly managed to alert Jeffrey right before she vanished. Edmund then brought Cassie to San Cristobel with the intention of keeping her his prisoner until she decided to be his princess. Fortunately, both Josh and Jeffrey were able to rescue her and Edmund was finally put in jail.

By 2006, Jonathan and Tammy had been arrested (thanks to Cassie) for arson when the house Sandy bought for Tammy was torched. Cassie begged Jeffrey to continue to deny Jonathan bail, arguing that the longer Tammy and Jonathan were apart, the more likely her daughter would to her senses. Jeffrey, however, disagreed, and to reunite the family and lied to Tammy that Cassie sent him to help get Jonathan a hearing. But when a thrilled went to thank Cassie, but Cassie refused to take the credit and told Tammy she hoped Jonathan stayed in jail forever. However, that wasn't meant to be since thanks to an impassioned plea from Reva, the judge granted bail. although Cassie was initially angry at Jeffrey's role at getting Jonathan out of jail, she softened when he admitted that he used to be a troubled kid like Jonathan and he was proof that someone could change his life around. Weeks later, Tammy and Jonathan's trial date arrived. Having had recused himself from the case, Jeffrey tried to appeal to ADA Doris Wolfe to drop the charges but she refused. Finally to protect Tammy, Jeffrey offered Doris a deal - drop the charges against Cassie's daughter, and she could have Jeffrey's job. Doris accepted and Tammy was freed. But The People still planned to put Jonathan behind bars. Jeffrey had one ace in the hole and that was Sandy. At the trial, Jeffrey was able to convince Sandy that sending Jonathan to jail wouldn't win him Tammy; playing hero might. When court reconvened, Sandy went up on the stand and stated that he was the one who started the fire.

Unbeknownst to Jeffrey, while he was at the trial, Cassie was in San Cristobel where she learned some unsettling things about him from Edmund. When Cassie returned how she confronted Jeffrey if Edmund's claims were true. Did Jeffrey work with Dinah in Europe to impersonate her and Richard? Jeffrey confirmed it was true. He was sent by the CIA to protect Richard and that included impersonating him. Jeffrey asked for Cassie's forgiveness; Cassie didn't say yes, but she didn't say no either. Jeffrey volunteered to stay at the Beacon until she made up her mind. The next day, Cassie allowed Jeffrey to come home, but things were still tense between them. Cassie still couldn't get over the fact that he'd impersonated Richard and wondered if he'd ever done it with her. When asked. Jeffrey denied it, but Cassie pointed out that, thanks to all the lies he's told, she couldn't exactly take him at his word. At this point, Cassie learned that dismissing the charges against Tammy had cost Jeffrey his job. Although touched, Cassie was still conflicted about Jeffrey's impersonation of Richard since she didn't know what memories of Richard were actually Jeffrey. Realizing that Cassie might do some investigating, Jeffrey called colleagues at the CIA, and demanded that all his records be destroyed, ASAP.

A few weeks later, Jeffrey was proven right when he spotted Cassie talking with Agent Malone and asked Cassie if she'd been spying on him. Cassie confirmed it and Jeffrey asked if Cassie wanted him to walk away from their relationship. Cassie wasn't ready to answer that question though. At that point, Jeffrey confessed his secret--while he was impersonating Richard, he fell in love with her. He then took her do Dinah who confirmed that he was so infatuated with her that while she and Jeffrey had sex, he called her "Cassie". After some angry words, Cassie walked off. To win back her heart, Jeffrey decided to come riding in on a white horse, like Richard had. However, while practicing, Jeffrey ended up getting thrown from the horse. Luckily, he was fine and was being tended to by Mel. Under pain medication, Jeffrey mistook her for Cassie and confessed another secret--he slept with Cassie while masquerading as Richard! In the meantime, Cassie was horrified to learn that Jeffrey had been in an accident. With no clue what happened, she rushed to his side and was relieved that he was only slightly injured. A few days later, for Valentine's Day, Jeffrey arranged for Tammy to visit her mother for Valentine's Day. Having resolved not to argue about Jonathan for the day, the pair had a nice visit. Afterwards, Cassie thanked Jeffrey for his gift and they declared their love. A few days later, Mel confronted Jeffrey with what she knew and urged him to tell Cassie.

Their conversation was overheard by Josh. Josh informed Jeffrey that although Mel might be bound by patient-doctor confidentiality, he was not. However, though Josh did urge Jeffrey to tell the truth, he assured Jeffrey that he wouldn't tell Cassie. Jeffrey came home to find Cassie ranting about her daughter being in love with a man who misrepresented himself in order to get her into bed. Seeing no other choice, Jeffrey came clean to Cassie. He tried to tell her that his love for her changed him but she was too horrified at the prospect that she cheated on her husband with him. Weeks later, Cassie and Jeffrey started reconnecting. However, while they began to make love, Cassie became unnerved and stopped when began having visions of Richard. Jeffrey demanded Cassie tell him where she expects them to go as long as she can't forgive him for impersonating Richard. He offered to move out, but Cassie wouldn't let him. He insisted, though, saying that being apart might be the best method for finding their way back to each other.

A few months later, Jeffrey was surprised when Cassie met up with and offered to buy him a drink and then suddenly kissed him. Although pleased, Jeffrey was confused since he was under the impression that they had both moved on. Cassie responded that she may be willing to give them another shot and suggested they go away for the weekend. However, when Josh found out, he strenuously objected and tried to convince Cassie that she'd be making the biggest mistake of her life if she went back to Jeffrey. Not appreciating Josh sticking his nose where it didn't belong, Jeffrey, Cassie and Josh argued with Josh finally carrying Cassie away. Not long after, as he expected, Cassie canceled her plans with Jeffrey. Meanwhile, a lonely and unappreciated Blake approached Jeffrey and suggested that they have another tryst. Jeffrey reminded Blake that they were opponents in a very bitter Mayoral race, and to be seen leaving together would be scandalous. He then got up and walked away--leaving her his room key, which she later used to join him.

In the meantime, Jeffrey continued campaigning and soliciting sponsors. However, while approaching Josh the two men ended up in an argument that turned into a scuffle. (Though neither would admit it the underlying cause was their feelings for Cassie) Meanwhile, during a scheduled debate with Blake, their previous tryst ended up shown live on television via the website SpringfieldBurns.com. Blake decided the only way to hold off the press was for her and Jeffrey to go public with their relationship, but Jeffrey thought since they were not in a relationship to just ignore it. Meanwhile, later that day, Jeffrey came upon Dinah skinny-dipping in the pond near the Beacon and she seductively pulled him in the pond with her. While they were kissing they noticed flames--the Beacon was on fire! Shocked, Dinah muttered something about what she'd done and ran to see if Mallet was alright. At the scene she found an injured Mallet who had gone into the burning building to save her. Jeffrey put two and two together and later accused Dinah of setting the fire. She was forced to admit that she did, though she believed it was out when she left the room.

Jeffrey was set to arrest Dinah but she begged him to bend the rules. Jeffrey decided to keep quiet, for a price. Days later, Jeffrey told Dinah what she needed to do to secure his silence--get Spaulding's endorsement for his mayoral campaign. In the meantime, Jeffrey was shocked to see none other than his old CIA boss, Ditkins, in the crowd during a campaign speech. Not only was Ditkins the man who got a young Jeffrey out of prison in exchange for working for the Agency; he was also the one who recruited him to alter his face (after he'd been beaten to a pulp by the husband of the woman he was sleeping with) in order to work undercover in San Cristobel. Ditkins was in town to warn Jeffrey against running for mayor--since there was information on Jeffrey could be damaging for everyone involved. Though Ditkins strongly implied that he would ruin Jeffrey if he ran for office, Jeffrey--determined to rise above his own past--defied him.

Meanwhile, when Dinah dragged her heels about getting the endorsement, Jeffrey put the pressure on, stating the DA needed a recommendation about the fire ASAP. Later, she met with Jeffrey on Main Street. After he again threatened her with jail unless she got his endorsement, she reminded him that she knew about his past--if it got out it could ruin his chances of becoming mayor. Dinah suggested that they needed to work together. Jeffrey conceded that she had a point and they agreed to keep each other's secrets. Unbeknownst to them both, their meeting was seen by Mallet who suspected that Dinah might have started the fire. When Mallet later demanded to know what was going on between him and Dinah. Jeffrey claimed they just made a deal for Spaulding's endorsement of his candidacy. Soon after, Jeffrey got the arson charges against Dinah dropped. Wondering why exactly Jeffrey had covered for Dinah, Mallet began looking into Jeffrey's past. Mallet and Gus located Jeffrey's old boss, Ditkins, who gave them a copy of Jeffrey's file--which would show why he wouldn't be mayor. Ditkins then alerted Jeffrey that the truth was about to get out, so he best back out of the race. Instead of backing out, Jeffrey ordered Dinah to get the file. Dinah went to Mallet's place and seduced him in order to grab the file. Later Jeffrey told his former CIA boss that he no longer worked for him and to stay out of his way if he knew what was good for him. The Feds tried again to ruin Jeffrey's chances at winning the election by sending his file to Alan-Michael. Luckily, Jeffrey found out and coerced Dinah into stealing it back by threatening to send her to prison. In the meantime, the friction between Mallet and Jeffrey grew, on the surface because Jeffrey was eager to win the election by being the hero and catching the blogger by himself. However, the root of their tension was clearly jealous over Dinah.

Meanwhile, Election Day finally arrived and with it Jeffrey gave Dinah her freedom by changing his locks—stating that she wouldn't get Mallet back if she kept running to him. He also got an unexpected visit from Ditkins who gave Jeffrey one last warning to drop out of the mayoral race or else. The day ended with Blake winning the election. However, while she was making her victory speech she suddenly collapsed! While Blake was rushed to the hospital, Jeffrey quickly took advantaged and announced that he would be resuming responsibility for the office until Blake was well. As he was making his speech, Jeffrey was suddenly interrupted by Mallet and taken downtown. Apparently, Blake didn't just collapse—she was poisoned. Mallet flat out accused Jeffrey of doing it but he denied it. That same day Jeffrey was confronted by an angry Olivia who stated that she'd had a baby from their dalliance years earlier but she had gotten rid of her.

Apparently, Jeffrey and Olivia were both crashed an Embassy party in San Cristobel and Jeffrey slept with a drunk and underage Olivia. As Jeffrey was reeling from this news, he was shocked to learn that not only was the poison meant for him but Blake herself was the infamous blogger. The next day, Jeffrey flashed back to Olivia's words and suddenly realized that if Olivia had gotten rid of the child while she was pregnant, she couldn't have known it was a girl. Jeffrey confronted Olivia who admitted that she put the girl up for adoption. Jeffrey agreed to not look for the girl as long as Olivia never made his past public. During their argument who should walk in but Ava Peralta---Olivia and Jeffrey's daughter! Afterwards, Olivia went to the paper and stated that Jeffrey had drugged and raped her when they were teenagers. Jeffrey immediately held a press conference and denied the charges but his reputation was sullied and Doris Wolfe fired him. Not only that, the governor forced him to step down as mayor. Weeks later, Jeffrey went to San Cristobel to try to remember what happened the night Ava was conceived. He finally remembered taking advantage of a drunk Olivia though he had no idea she was only 16. Olivia was there as well and confessed that she purposely made herself look older that night and she did flirt shamelessly with him so the fault was partly hers.

As Jeffrey apologized for his part, Olivia told him that to make it up to her he should stay away from Ava. However, although she didn't necessarily want a familial relationship with Jeffrey, Ava did tell him that she wanted to be friends.. Meanwhile, Ava had decided to move to London with Coop. Before she left, Ava gave Jeffrey a Swiss army knife as a birthday present. Though Jeffrey tried to unaffected, it was obviously that her gesture touched him. As Ava and Cooper were at the airport ready to leave, Jeffrey rushed in while Ava had walked off. Jeffrey tried to tell Coop that he wanted to give Ava a Christmas present but Coop convinced Jeffrey that it would be best to just forget about Ava since Jeffrey would only hurt her in the long run anyway. Meanwhile, Ava discovered that Coop kept a job offer from Alan-Michael from her and disappeared from the airport and went to Outskirts where she was aggressively pursued by a man named Duke, when Jeffrey unexpectedly showed up to get him off Ava. Jeffrey tried talking with Ava but she was a bit defensive and left. As she was leaving, Duke called Ava a slut and Jeffrey punched him. Unfortunately, two of Duke's goons surrounded Jeffrey and beat him up. Later, when Ava learned that Jeffrey had been injured in a fight she rushed to see him at Cedars. There she also found a pair of earrings with her birthstone. Jeffrey admitted that they were a Christmas present for her but Coop talked him out of giving them.

In 2007, Jeffrey warned Coop about Alan-Michael taking Ava to Paris on business and got Alan-Michael's address so Coop could follow them. Weeks later, Jeffrey approached Alan-Michael and demanded that Ava be let out of her contract stating that Alan-Michael violated it by taking her to Paris under false pretenses. Alan-Michael denied the charge and accused Jeffrey of using legal tactics to get close to his daughter.. Meanwhile, Buzz visited Jeffrey and told him to turn down the invitation Olivia was going to send to her wedding. However, Jeffrey didn't feel that he had to. Later, Jeffrey caught Ava doing some spy work for Alan-Michael regarding the investigation into Alan's shooting. Jeffrey urged her not to trust Alan-Michael and warned that she was an accessory to a crime by soliciting this information. However, Ava defended Alan-Michael's intentions and apparent innocence. Ava left angry and days later, Jeffrey was distressed to learn that she was moving into the Spaulding mansion to take care of a seemingly paralyzed Alan-Michael. Jeffrey tried to keep Ava from moving in by arranging for Ava to meet with Olivia, but in the end Ava moved in the mansion anyway. Later, Ava asked her parents to help her keep Doris from taking control of Spaulding. Though Jeffrey refused to help since he believed that Alan-Michael was a bigger threat, Olivia agreed to help. Later, after Alan-Michael insulted Olivia, Jeffrey punched him just as Ava arrived. When Olivia helped Jeffrey with his bruised hand, she admitted that while nothing would excuse what he did to her when they were young, she recognized that he is not that same person now. Their faces came close, but they resisted a kiss. Meanwhile, the pair was still concerned about Ava's relationship with Alan-Michael and kidnapped Alan-Michael to warn him away from her. Though Jeffrey tried to bribe him, Alan-Michael refused to concede to their demands.

In the meantime, Ashlee Wolfe finally confessed to shooting Alan. With Jeffrey's help she was tried as a minor and remanded to juvenile detention. In the midst of all this, Jeffrey started to develop feelings for Olivia. Meanwhile, Ava was concerned about Olivia's anger toward Jeffrey and encouraged him to accept his invitation to her wedding. Jeffrey declined though Ava was able to convince him to visit Olivia the night before her wedding and ask for her forgiveness. Unfortunately, Jeffrey showed up at Olivia's slightly inebriated and ended up pulling Olivia into a passionate kiss. Even more unfortunate, Alan Michael had not only seen the whole thing but had taken pictures. As revenge for the kidnapping, Alan-Michael sent the photos to Buzz who immediately called off the wedding. Devastated Olivia told the news to Jeffrey who held Olivia's wrists as she tried to hit him and the two kissed – just as Buzz arrived to see.

Soon after, Olivia confessed to Buzz that she was confused about her feelings and could not marry him. The next day Buzz talked to Jeffrey about his feelings for Olivia. When Jeffrey seemed noncommittal, Buzz warned that Olivia deserved to have someone who could be counted on. Taking Buzz's words to heart, Jeffrey decided to leave Springfield. That's when fate stepped in the form of Cassie. At this point, Beth was pregnant with a child that may or nay not have been Alan's. Cassie was certain that Alan had paid a lab tech to rig the upcoming paternity test in his favor and begged Jeffrey to help her to stop him. Jeffrey quickly found the technician (who was throwing money around at Company as if he had been bribed) and arranged for him to be replaced with someone else. Meanwhile, having already said a heart felt goodbye to Ava, Jeffrey decided to stay in town after all. In the meantime, Olivia tried to get Jeffrey interested in her by continually asking for legal advice and even flirting with other men. However, Jeffrey rejected her efforts because he didn't want to hurt her.

In the meantime, the Spauldings were contending with the fact that Lizzie had disappeared for a few days and returned with no memory of what happened. Soon, Alan went to Jeffrey with the accusation that Reva had drugged and kidnapped Lizzie. When Alan mentioned a tattoo that Lizzie had mysteriously gotten, Jeffrey suddenly remembered that he saw Reva with a tattoo recently. Jeffrey took Alan and Lizzie and confronted Reva who stated that she and Lizzie went on a wild bender in order to get over the pain of Jonathan and Sarah's deaths. Having no memory of the weekend, Lizzie believed Reva. Though he told Alan that he had no case, Jeffrey later confronted Reva and asked why she lied. However, Reva denied she was lying. Days later, Jeffrey spotted Reva talking with a mysterious man. When he asked about him, Reva spun a story which Jeffrey was skeptical about. Meanwhile, Olivia unexpectedly arrived at Jeffrey's and tried to seduce him. Though he tried to turn down her advances, he was about to give in when Reva called him stating that she had been arrested. At the police station, Jeffrey demanded that Reva tell him the truth but she stuck to her story about it simply being a wild weekend. After Lizzie mentioned that her tattoo hurt at the bone, Jeffrey had a revelation and confronted Reva with his suspicion: Jonathan and Sarah were actually alive. Reva tearfully admitted that Jonathan was forced to fake their deaths in order to keep Sarah away from Alan and pleaded with Jeffrey to keep the secret. Knowing that a suspicious Alan would be watching her, Jeffrey suggested that Reva stay at his place.

Later, Jeffrey agreed to have dinner with Olivia to see if their relationship could progress further, however, he got wrapped up in helping Reva and forgot about his date. Afterwards, a kiss from Reva quickly turned into a night of lovemaking. Since they were both out of complicated relationships (him with Olivia, her with Josh), they decided to use one another for comfort. In the meantime, Ava was mysteriously mugged. When nothing was taken and Ava was only mildly injured, Coop theorized that the attack was about sending a message. Jeffrey thought Coop was on to something and suspected that someone from his past was involved. Soon after, Jeffrey overheard Reva accuse Olivia of hiring someone to mug Ava in order to snare Jeffrey's attention. Disgusted, Jeffrey told Olivia that he wanted nothing to do with her. Days later, Olivia confessed her feelings and kissed Jeffrey, but he pushed her away. At the same time, he and Reva were becoming closer.

Later, Olivia asked Jeffrey's forgiveness but he refused to give it. Afterwards, Jeffrey invited Reva to go to Hawaii with him but she inexplicably refused. She then told him that she wanted to end things, which confused Jeffrey since they were only having fun to begin with. In the meantime, Jeffrey had seen Olivia in a few arguments with Reva and warned Olivia not to fight Reva over him. He told Reva the same thing—reminding her that when she and Olivia go toe to toe bad things happen. Days later, he was proven correct when Reva was hit by Olivia's car. Though he initially believed Olivia's claim that it was an accident, he became skeptical when no skid marks were found: Olivia hadn't even tried to stop. Again Olivia declared that it was an accident and was frustrated that Jeffrey wouldn't take her word. Despite his doubts, Jeffrey defended Olivia when she was arrested for attempted murder. Soon after, Reva stepped up and confirmed that it was indeed an accident. After Reva's testimony, Jeffrey took her home and the pair made passionate love. Weeks later, Olivia spitefully evicted Jeffrey from the Beacon and Jeffrey reluctantly accepted Reva's offer to move in with her. Later, Olivia surprised Jeffrey by confessing that she blackmailed Reva into breaking up with him by threatening to reveal that Jonathan and Sarah were alive. That was why Reva tried to break up with him earlier. However, Olivia was now ready to let go of and forgive Jeffrey. Then one day, Jeffrey found that the cabin had been ransacked and Reva was missing. With Alan out of town as well, Cassie and Jeffrey became concerned that Alan had done something to Reva. Taking a lead, which proved to be false, from Cyrus Foley, Jeffrey fled to Mexico to search for the pair.

Days later, Jeffrey returned as and told Cassie that Reva and Alan were both gone. When Alan returned home, Cassie pulled a gun on him and demanded to know what he did to her sister. Luckily, Reva stepped out of the villa and the pair informed a skeptical Jeffrey and Cassie that they had ironed out their differences and called a truce. However, Jeffrey was convinced that Alan was holding something over on Reva and did some digging into where they went. Afterwards things got stranger when Reva announced that she feared getting closer to Jeffrey and was moving into the Spaulding mansion. However, Reva quickly decided to move back to her house and her life with Jeffrey. Meanwhile, Jeffrey asked Mel to look into where Alan went on Sept. 14. Later, he found a clipping from Tourmaline after he learned that Alan's jet landed in Northern California. Suspicious, he went to California to investigate. When he returned home he pointedly mentioned Tourmaline to Reva. At that point, Reva confessed the entire truth to Jeffrey. Apparently, Alan got a tip on Jonathan's whereabouts and went to California to meet the person who called him, the local sheriff. The sheriff attacked Reva and Alan killed him to save her life. An understanding Jeffrey informed her that she had to turn Alan in before Alan turned on her. However, Reva refused, fearing that Alan would discover the truth about Jonathan. (with the sheriff's death, Alan had no proof that this was true) Afterwards, in order to save Reva, Jeffrey fed the authorities in CA with the suggestion that the sheriff was killed by people he owed money to.

Weeks later, Reva talked to Jeffrey about Cassie wanted to get custody of her son Will, now living in San Cristobel. Though Alonzo refused the give up custody, Cassie decided to fight. While compiling a list of suitable witnesses who could testify on Cassie's fitness as a mother Edmund's name came up and Cassie decided to seek his help. Jeffrey not only learned that Edmund was currently in a mental hospital in San Cristobel , he was also on Alonzo's witness list. Since Edmund's testimony had to be conducted in person, Jeffrey, Josh and Cassie flew to the island. While at the hospital, Cassie got separated from Josh and Jeffrey when the power suddenly went out. Moments later, the generator kicked on and Jeffrey and Josh found Cassie with Will, Edmund and a dead Alonzo. Though Jeffrey accused Edmund of pushing Alonzo into the generator box, a deranged patient later confessed. With Alonzo's death, Cassie took her son back to Springfield. Unfortunately, Will had a very hard time adjusting to his new life and kept asking for his best friend—Edmund. Though Jeffrey objected, Cassie asked him to arrange for Edmund to be brought to the States. Upon his arrival, Edmund was pardoned by the Secretary of State and was a free man which Jeffrey was not pleased about. Later, Reva found Jeffrey watching the farmhouse and confronted him about being Cassie's protector. Jeffrey admitted that old habits were hard to break and agreed with her that Cassie was no longer his business.

Later, Josh went to Jeffrey, wanting to hire him – not as a lawyer, but to get rid of Edmund permanently. Josh informed Jeffrey that Cassie switched Beth's paternity test to show that Rick was the father and Edmund now knew about it. Jeffrey made sure of the seriousness of what Josh was asking him to do and Josh reiterated that Edmund needed to be taken care of to protect his family. The day before leaving for Montana, Jeffrey met up with an old CIA colleague, Roc Hoover, and arranged for him to kidnap Edmund and transfer him to a secure location where he would be bound and gagged. After Thanksgiving, Josh called Jeffrey to find out what exactly had been done to Edmund and Jeffrey assured him that Edmund was alive. He then told Josh his plan. Edmund would be given a choice: either be tried and executed for Alonzo's murder or spend the rest of his life in a maximum security compound called Peaceful Valley. When presented with the plan, Edmund scoffed at first but he realized that Jeffrey intended to frame him for Alonzo's murder, he had no choice but to choose prison.

Unfortunately, things got a little complicated when Will begged Edmund to stay in town long enough to see him in the Christmas pageant. Cassie unexpectedly agreed, and Jeffrey was forced to hide Edmund away at the cabin. Reva was not happy to find Edmund in her house. Jeffrey told her about Edmund threatening Josh and Josh asking for help, and the plan to force Edmund into the prison compound. Later that day, Jeffrey shocked Reva by admitting that he lied. There is no Peaceful Valley: Edmund would be executed. Conflicted, Reva went to Billy who assured her that Edmund really did have to be stopped by any means necessary. Days later, Reva and Jeffrey attended Josh's ordination as minister which corresponded with the children's Christmas pageant. Though the pageant was not over, Jeffrey dragged Edmund out and informed him that there was no Peaceful Valley. Edmund would be executed for Alonzo's murder. He then placed Edmund in his accomplice's care. Somehow, Edmund escape and the moment that Josh was ordained, all were shocked to see Edmund fall from the balcony at his feet. Edmund was rushed to Cedars, alive but comatose. At Towers, Reva, Jeffrey and Rick realized that any one of them could have pushed Edmund and went over their cover story. The following day, Reva could not help herself from wondering if Jeffrey pushed Edmund. When Jeffrey sensed her doubt, he assured her that he did not do it though whoever did deserved a medal. In the meantime, Edmund had been transferred to a hospital in San Cristobel. As Edmund was beginning to wake up, Jeffrey messed with his IV in an effort to keep him comatose and out of everyone's life.

In early 2008, Jeffrey agreed to return as District Attorney. Happy for him, in the heat of the moment Reva blurted out that she loved him. In the meantime, the police got an anonymous tip about Reva being involved in Edmund's fall. Looking through Reva's things, Mallet found Edmund's buttons in her purse. Reva was brought in for questioning and afterwards she and Josh suspected that Will set her up. Jeffrey, however, unexpectedly hurt Reva by assuming that she was guilty. Soon after, Josh and Reva got Will to admit to pushing Edmund. At the police station, Will confessed that Edmund .threatened to hurt Cassie and Will lashed out—making it sound like a tragic accident. Soon after, Jeffrey checked out the surveillance tape of Alonzo's accident. Scanning the tape, Jeffrey noticed something startling—Will deliberately pushed his father into the electrical gate! Jeffrey showed the tape to Josh and told him that this changed everything. Jeffrey now wanted Will remanded into custody and sent to a juvenile facility. At the same time, Will confessed to his mother that Edmund's death was no accident and Cassie spirited the boy to the Bauer cabin so she could talk through his violent tendencies. Jeffrey and Josh soon located Cassie and told her about Alonzo, but she protested when Jeffrey tried to take Will into custody. Cassie convinced Jeffrey to let Will stay at the cabin with her and Josh for a night. However, since Tammy's memorial service was coming up, Jeffrey must have taken pity on Cassie and let Will stay with her longer.

Meanwhile, Jeffrey was able to get Will into Fairmont but Cassie resisted and proclaimed that she promised Tammy she would not send Will away again. Apparently out of respect for Cassie, Jeffrey did not fight her. Meanwhile, Lizzie finally learned that Jonathan and Sarah were alive. Doris demanded that kidnapping charges be brought against Jonathan and despite his allegiance to Reva, Jeffrey knew he had no choice but to comply. Luckily, it became a non issue when Lizzie refused to press charges. Meanwhile, on day Cassie overheard Josh, Jeffrey and Reva discussing Will and angrily accused them all of plotting to take her son away. When Reva tried to reason with her, Cassie violently shoved her.

Later, Jeffrey and Reva found Will with Cassie at the Cross Creek cabin and the place in disarray. Though Cassie tried to convince them that she was the culprit but they realized that Will was responsible. Having had enough, Jeffrey had charges brought up against Will. Cassie tried to dissuade Jeffrey by playing the damsel in distress and talking about whether they breaking up was a mistake, but Jeffrey gently told her that the past was in the past; they had both moved on. He then explained to her that Will needed to be sent to juvenile detention for his own good. Afterwards, Jeffrey laid down the law to Will about what to expect and what was expected of him. However, the only response he got was Will's question about what it would have been like to push Jeffrey off the balcony. In the meantime, though Reva wanted Jonathan to stay in town and fight Alan, Jonathan felt the risk was too great and told Jeffrey that he planned to leave. Per Jon's wishes, Jeffrey kept this from Reva who was later a bit hurt when she found out. Meanwhile, Jeffrey paid Will another visit and was almost shocked by a taser gun that Will swiped from the guard. Luckily, Jeffrey grabbed the taser away before Will could use it and reprimanded the guard about being careless with his weapon. In the meantime, Cassie was using her feminine charms on the guard to get him to grant her unauthorized visits with Will. When Jeffrey put a stop to that by telling Josh that Cassie was getting out of control, Cassie went to a judge and convinced him to release Will—arguing that he was just a little boy who needed his mother's love. In the end, Cassie realized she was wrong when Will attempted to murder Josh and Reva and she willingly handed Will over to the police.

Soon after, Reva surprised Jeffrey by asking him to have lunch with Olivia. At lunch, Olivia confessed that she was dying from a weak heart. Although her name was high on the transplant list, the prognosis was very grim—Olivia had mere days to live. Olivia then asked Jeffrey for a favor: she wanted him to marry her and Gus. Olivia explained that she knew this wouldn't be a real marriage since Gus was already married. She just wanted to die married to the man she loved. Unfortunately, Gus refused to be a part of the ceremony which crushed Olivia. When an upset Olivia told Jeffrey that her friendship with Gus had given her hope and faith in love again, Jeffrey offered to marry her himself. Touched, Olivia accepted and Jeffrey got Doris to officiate a beautiful outdoor ceremony. Immediately after, Olivia collapsed and was rushed to Cedars in critical condition. As Jeffrey waited at the hospital with Ava, they learned that a heart was available for immediate transplant. Unfortunately, when Jeffrey and Ava went to Olivia's room she had disappeared. Since no one had any idea where Olivia was (Reva smuggled her out for bit) the heart was given to someone else.

Later, Olivia finally returned while at the exact same time Gus was wheeled in after suffering a severe head injury in a motorcycle accident. Despite Rick's best efforts, Gus died on the operating table though Jeffrey kept that news from Olivia. When it was learned that he was a match, Gus's widow, Natalia, permitted Olivia to get his heart. As this was going on, Ava told her father that she suspected that she was pregnant with Bill's baby and was disappointed when a test confirmed otherwise. Meanwhile, when Olivia learned that she was alive after receiving Gus's heart, she went into a deep depression. To give Olivia a reason to live, Ava lied that she was pregnant and told Jeffrey not to say anything. Though he agreed, Jeffrey ultimately spilled the beans to Olivia. However, Ava continued to lie to Bill about the baby. Meanwhile, when Olivia was released from the hospital, Jeffrey invited her to stay at the cabin so he could take care of her. When Olivia got stronger, she opted to move out and she and Jeffrey divorced. Meanwhile, Ava suddenly announced to Jeffrey that she really was pregnant. Days later, Jeffrey got another shock when Reva's father, Hawk, arrived and announced that he was staying for an extended visit.

It didn't take long for Hawk to tell Reva his reason for coming—he sold the rights to her life story to a movie producer. Though overwhelmed, Reva decided that it might be fun and allowed the movie to be made. Ultimately, the producers decided that the movie should center on Reva's love story with Josh. Though Reva worried when Jeffrey read the script, he assured her that he liked it. Unfortunately, the filming of Always at the cabin was disruptive so Reva and Jeffrey moved into a hotel temporarily. Meanwhile, Harley had returned to the force and went to Jeffrey with her suspicion that Gus had so many unsolved cases because a crooked cop was obstructing them. Jeffrey went to Mallet (now the temporary police chief) with his concerns but Mallet assured Jeffrey that Harley had no proof. Unconvinced, Jeffrey decided to launch a full scale investigation into the department. Fearing that the investigation might turn to Mallet's direction, Dinah informed Jeffrey that Gus himself was the crooked cop and Mallet destroyed evidence to protect his reputation. Very soon after, Harley discovered Gus's motive-- was letting a certain defense attorney's clients slide in exchange for getting Olivia's name on the top of the transplant list. Since Jeffrey had already opened up the investigation and needed to make some kind of statement to the press. Unfortunately, Mallet shared this with Gus's teenaged son, Rafe, and Rafe responded by stealing Gus's gun and threatening Jeffrey into protecting his father's reputation. While Jeffrey tried to talk Rafe down, Mallet entered, startling Rafe. Unfortunately, the gun went off, hitting Jeffrey in the chest. As Mallet called for help, a stunned Rafe ran out and soon fled the country with Harley. As for Jeffrey, he recovered and lied that the shooting was an accident. During his recovery, Reva told Jeffrey that she wanted to marry him.
Meanwhile, Jeffrey was not pleased to learn that Ava was marrying Bill since he figured out that the baby Ava was carrying was not his. In fact by this point, Jeffrey knew that Ava had had herself artificially inseminated. Though Jeffrey argued that it was wrong, Olivia urged him to be happy for his daughter. Several days later, Jeffrey saw Bill kissing Lizzie. Determined to protect his daughter from being trapped in a loveless marriage, Jeffrey arranged for Lizzie to discover that truth and then verbally confirmed that Ava lied about being pregnant with Bill's baby. Though Lizzie went to Bill with the news, Bill surprised everyone by going through with the wedding. In the meantime, the filming of Always continued and Jeffrey and Cassie were shocked at the ending which had Josh reuniting with Reva during the cancer scare. Though Josh and Cassie were both outraged, Jeffry shrugged it off as just a movie. However, it became apparent that the movie was stirring up buried feelings in Josh and Reva. When filming commenced, Josh declared his love for Reva but she informed him that Jeffrey was the man she wanted to be with. Afterwards, Reva asked Jeffrey to marry her as soon as possible. Not long after, Ava's baby, Max Harlan Lewis, arrived, several weeks premature. To everyone's shock—the baby was black. It immediately became obvious to Ava that her original positive was false—Max was Remy's baby. Unfortunately, an already overwhelmed Ava was hit with a bad case of post partum depression and, fearing that she might hurt herself or Max, Jeffrey sent her to a clinic in Chicago. Though Bill threw all of his energies into obtaining legal custody of Max, Jeffrey wasn't so sure that was the right thing and made plans to have Bill's name taken off of the birth certificate. Sadly, it became a moot point when Max died.

Worried about Ava, Jeffrey threw himself into his work, working tirelessly to convict Alan and Grady Foley for Tammy's death. Unfortunately, thanks to perjured testimony from Daisy, Tammy's death was ruled an accident. Though an opportunity to nail Alan seemed to arise when Lizzie offered to testify that Alan hired Grady to kill Jonathan, that fell through when Lizzie backed out.

Meanwhile, after dragging his feet about a wedding date, Jeffrey suddenly decided to marry Reva immediately and with help from Buzz, put together an impromptu ceremony. The day of the wedding, Reva told Jeffrey that she'd found a mass in her breast that could be cancerous. That same day, Josh came to talk to Reva. He was interrupted by Jeffrey and soon the two were in a brawl. Reva quickly broke it up and railed at both men. At that point, she told Josh about the mass she'd found. After Josh left, Jeffrey and Reva married with the Coopers in attendance. The next day, the pair went to Cedars to learn the results of the biopsy. Anxious, Reva left Cedars and went to Company to distract herself. While she was gone, the doctor gave Jeffrey shocking news—Reva didn't have cancer; she was pregnant. When Jeffrey informed a shocked Reva, they returned to Cedars where they learned that 1) Reva hadn't completed menopause and more importantly 2) her cancer medicine also acted as a fertility drug. The main problem was that Reva had to go off the cancer medicine during her pregnancy which could lead to a relapse. Jeffrey confided in Lillian and Buzz and came to the conclusion that, though he wouldn't mind having a child, Reva's health took precedence. However, ultimately both he and Reva decided that it was worth the risk. In the meantime, Olivia informed Jeffrey that although Ava was being released from the hospital, she did not want to return to Springfield. As for Reva, Jeffrey spent the next several weeks calming her fears about how the pregnancy would affect her life. Though Reva wanted to continue to live her life the way she had been, Jeffrey cautioned her that since she was in a high risk pregnancy she needed to let him handle things. Meanwhile, Jeffrey got a job offer from the President-elect, Though, he decided to refuse, Reva insisted that he leave for Washington to discuss it.

However, Jeffrey worried about Reva being alone and insisted that she stay at the Beacon. Soon after, Reva moved back home and almost collapsed. She was discovered by Josh who called Jeffrey. At Cedars, the pair learned that Reva had leukemia. When the doctor told them to terminate the pregnancy, the two went to Colin for a second opinion and Colin informed them that Reva's chemotherapy would not harm the baby. Several weeks later, Jeffrey and Reva were in for another shock---Shayne was in Springfield. Even more shocking was the knowledge that Shayne was injured while clearing a land mine and was in a wheelchair. Though both Josh and Reva tried to get Shayne to discuss what happened, he refused to talk about it. In fact, he seemed emotionally closed off. Later, Shayne asked Jeffrey for his help to reenter the Peace Corps. Knowing that Reva wanted Shayne to stay, Jeffrey pleaded with Shayne to stay and informed him that his mother's cancer had returned. When Shayne got the call anyway from the organization, he incorrectly assumed that Jeffrey reconsidered. Knowing that concern for Shayne was causing Reva stress, Jeffrey blocked him from leaving the country. At year's end, Reva asked Shayne to be her baby's godfather.

In 2009, Jeffrey tried to help Shayne by getting him interesting in helping troubled teens at the Community Center. Jeffrey was determined to give Reva a stress free pregnancy and the key to that was helping Shayne. Dinah wanted to help Shayne as well and when she found a photo of a girl, she assumed that it was Shayne's girlfriend and asked Jeffrey to find her. It didn't take long for Jeffrey to learn that the girl, Lara, was dead. Soon after, Shayne confessed to his parents that Lara, who Shayne was in love with, was killed in a minefield. Eager to give a tortured Shayne closure, Josh and Reva arranged an impromptu memorial service for Lara. The family was shocked when Edmund showed up at the service and announced that he was Lara's father. According to Edmund, Lara came to him while he was in the hospital and confessed that she was his daughter from an affair with a servant girl. Edmund's situation reminded Jeffrey of his own with Ava and he convinced Reva and Josh to let Edmund stay in town to speak to Shayne. When Dinah warned Jeffrey that Edmund was dangerous, Jeffrey assured her that Edmund was being watched.

Weeks later, Jeffrey discovered Reva's videos and accused her of giving up. Reva had just had her last chemo session and Jeffrey felt that she had to remain positive that she would survive. As the days went by, Reva prepared for the worst while Jeffrey did not even want to acknowledge the fact that Reva might die. In the meantime, Olivia was trying to sort through her personal issues and confided in Jeffrey that she was beginning to have feelings for Natalia Rivera. Jeffrey was surprised but supportive and encouraged Olivia to tell Natalia how she felt. Meanwhile, Colin informed Reva and Jeffrey that the chemo was unsuccessful and they needed to bombard Reva with a massive dose of radiation. However, her baby had to be delivered immediately by C-section before they could begin. Though Reva was almost to term, it would still be a premature birth and Colin could not guarantee that the baby would be developed enough. When Reva refused to deliver the baby early, despite the risks to her own health, Jeffrey used the power of attorney that he'd gotten from her and obtained a court order to force the delivery. Reva took it to court. During the trial, Jeffrey and Reva finally understood their positions and came to a compromise—they'd chart her progress and the baby's progress.

Not long after, Reva had her baby whom she named Colin. While Jeffrey was able to take the baby home, Reva was forced to stay at Cedars to undergo radiation treatment. Jeffrey set up a web cam at home and gave Reva a lap top so that she could see Jeffrey and Colin. In the meantime, Josh learned that Shayne told Edmund about the circumstances of Lara's death—that she had died after Shayne failed to defuse the minefield. Convinced that Edmund would react violently, Josh approached Jeffrey and asked for his help in getting rid of Edmund. Both men agreed to keep this information from Reva who was in the hospital getting cancer treatments. Since Jeffrey was alone with Colin, he was unable to handle the situation himself and gave Josh his contact list. Josh immediately contacted Roc who promised to keep an eye on Edmund. Unfortunately, Edmund quickly got the better of Roc and knocked him unconscious.

After finding Roc, Josh rushed to notify Jeffrey at both men were shocked to learn that both Reva and Colin were missing. Thanks to the webcam, Reva saw Edmund at the cabin and was able to stop him before he took Colin. Worried that Jeffrey would kill Edmund, Reva kept the near kidnapping a secret until Josh got Edmund out of town with Roc's help. After days of without contact from Roc, Josh went to Jeffrey who assured him that everything was okay—the long periods of silence were normal in these situations. However, Josh was unconvinced and became paranoid that Edmund was still a danger. Despite Jeffrey's assurances that everything was fine, Josh still saw danger everywhere—even overreacting when Reva got a package without a return address. Josh's behavior began annoying Jeffrey and he told Josh in no uncertain terms to back off from Reva. However, Josh was vindicated when they discovered that Edmund had subdued Roc and was on the loose. Not long after, Edmund turned up in Springfield—dead. Though Reva told Mallet that she had not seen Edmund in town, Olivia told Jeffrey that she'd seen Reva and Edmund arguing. Confronted by Jeffrey, Reva admitted that she'd argued with Edmund and made a deal that if he left immediately and never returned, she wouldn't tell anyone that he had come back to town. Meanwhile, Christina Moore identified Reva's voice as the one she'd heard with Edmund on the day he died. When a videotape was seen Reva in the vicinity of where Edmund was killed, she was booked for his murder.

Determined to prove Reva's innocence, Jeffrey began an investigation. When he attempted to examine Edmund's body, he was shocked to learn that the body was cremated and the ashes scattered over the lake. Jeffrey quickly theorized that the body in the water might not have been Edmund after all. Suspecting that Edmund was alive and was setting up Reva for murder, Jeffrey doctored the evidence to make it appear as if he had committed the murder. Jeffrey let Josh in on his plan and asked him not to tell Reva. After arranging a family picnic, Jeffrey left without telling Reva goodbye. However, Dinah caught wind of his plan and convinced him to let her help nab Edmund. He and Dinah flew to Europe in an attempt to lure Edmund out of hiding by making it appear that Lara was alive.

After weeks of merely texting Reva, Jeffrey finally called her to say goodbye when it appeared as if his airplane was going down. At the same time, Dinah returned to Springfield on her own and confirmed that Jeffrey's suspicion was correct—Edmund was indeed alive. Meanwhile, having survived the crash, Jeffrey made his way to Jonathan's. As Jonathan was nursing Jeffrey back to health, he received a call from Edmund who threatened to take Sarah. To lure Edmund out of hiding, Jeffrey decided that he had to let everyone believe that he was still dead. Using a doll of Sarah as bait, Jeffrey succeeded in luring Edmund out. Unfortunately, Edmund got away and promised that he would murder all of the Lewis children unless Jeffrey continued to let Reva believe that he was dead. Apparently, Edmund's main goal was to make Reva suffer. Jeffrey swore Jonathan to secrecy and then kept in contact with him for several weeks. Through the next few weeks, Jeffrey came close, but not close enough, to nabbing Edmund. Edmund warned Jeffrey that he was keeping close tabs on what was happening in Springfield. Jeffrey and Edmund's cat and mouse game continued with Edmund speculating that Jeffrey enjoyed the chase

It is unclear what became of Jeffrey but as of the fall of 2010 he was still presumed dead. Jeffrey could have been killed or he could have finally apprehended Edmund or killed him. Having gotten a taste of his former carefree secret agent lifestyle, Jeffrey may have decided to simply stay away from Springfield or he may be on his way there now.