Simon Frasier came to Oakdale with one goal: retrieving a family heirloom. Apparently his great-grandfather gave his beloved a very valuable necklace and Simon was determined to retrieve it for himself. When Simon saw a picture of Lily Snyder in a magazine, he was struck by her resemblance to “Beloved” and, figuring that Lily must be a descendant, he ingratiated himself into her life in hopes of recovering the necklace. Simon planted his great-grandfather's love letters to “Beloved” in a place where Lily would find them. Finally, Simon came to retrieve his "lost" letters. After talking with Lily, he told her that he was a architect and talked her into letting him renovate her home and later paint her portrait. When Lily finally found out that she'd been lied to, Simon confessed his interest in finding Beloved's descendants, but didn't tell her anything about the necklace. Simon's search hit a dead end and he enlisted Lily's help.
Unfortunately, Simon couldn't get Lily's help willingly, so knowing she would be curious about her family background, he followed her hoping she would lead him to the diamond necklace. When Lily packed up to go to Atlantic City, Simon knew it had something to do with his search, and trailed her. There, he made a spectacular discovery: he'd been following the wrong girl! Apparently Lily never had the diamond, a showgirl (who was a dead ringer for Lily) named Rose had it. Though Simon tried to con Rose out of the diamond, she chose to trust Lily and refused to tell him where it was. Simon was determined to get his diamond, however, and confronted both women, but this time he was unable to tell them apart. At that point, shots rang out, one woman ran and the other was knocked unconscious. Trying to escape the shooter (whose identity Simon knew), Simon grabbed the woman and they both boarded a passenger train. The woman stayed unconscious for days until she awoke. Though Simon pleaded with the woman, who claimed to be Rose, to tell him where the diamond was, she refused. By the time he'd discovered that he was with Lily, who told him where she hid the diamond, the train had unhooked itself and they were in the middle of nowhere. Luckily, they weren't far from a town and so he and Lily left the train. Though Lily wanted desperately to go home, Simon was adamant that she stay with him until he found his diamond.
Finally, Lily was forced to tell him that she lied about the diamond: she had no idea where it was. Though Simon tried to protect Lily from the mysterious shooter, who ended up being his demented sister, Celia, he was unsuccessful and they both ended up being held hostage. When Celia learned that neither knew where the diamond was, she decided that they were both expendable and tried to murder them by having them jump out of an airplane. After spending months on the island, Simon started to fall in love with Lily. Just when all hope for a quick rescue seemed lost, the castaways learned that they weren't alone on the island. Unfortunately, one inhabitant was a criminal who only wanted to make love to Lily and the other was Simon's sister, who stranded them in the first place! After evading an assassination attempt by Celia, Simon and Lily were able to imprison her. Unfortunately, she escaped and tried to leave the island on the raft Simon was building. Tragically, a large current came and capsized the raft sending Celia and the beloved diamond to a watery grave. Not long after, Simon and Lily were finally rescued and returned to Oakdale.
Simon's return to Oakdale was immediately fraught with legal problems, which luckily Lily was able to help him get out of. By this point, Simon was in love with Lily, who unfortunately was torn between him and her husband. Not long after he drunkenly made love to Katie Peretti, Simon found out that he was in danger of being deported. Desperate to stay in the country to remain close to Lily, Simon married Katie. Despite Katie's many attempts to make their marriage real in every sense of the word, Simon continued pining for Lily. They nearly made love more than once before Katie announced a pregnancy. Lily backed off, and a drunken Simon, realizing Lucinda had called INS, drove his car into her living room, proclaiming this her judgment day. Margo arrested him shortly afterward, and, while the trial was pending for the various charges, Simon learned Katie had faked her pregnancy. As the trial began, Katie made a deal with Lucinda to drop all charges if Katie agreed to keep Simon and Lily apart. Simon saw them together, and, while grateful, a few weeks later decided he wanted to go back to Australia. Katie told him she did her best to make him happy, he had reason to be happy, but all he ever did was mope. He agreed to spend a few more hours with her, and by the time he came out of the shower, she'd decorated their entire garage apartment with balloons. She pulled the towel off him and they rolled around on the floor laughing, almost making love. Katie convinced him to stay another day, and then asked her brother, Craig, to give him a job. Craig hired him to dig up information on Ruby Frank, who had been made several attempts to seduce him and capture the results on tape. Katie and Simon moved into a suite paid for by Craig.
Around the same time, Katie, after asking Henry Coleman to dig up info on Simon's past, learned Simon had been married 5 times and engaged twice. Katie overheard Simon trying to find a way to connect with Ruby, and accused him of looking for rich wife #6. Simon assured her he never married women for their money, even if some of the marriages had been out of convenience. Simon arranged to bump into Ruby at Yo's, flirting with her, charming her, finally dancing with her and kissing her. Katie yelled for Ruby to back off of her husband and the two women fought with pool cues until Simon dragged Katie outside. His explanation that he was conning Ruby was little help, and Katie spent the next few months following him around, warning Ruby, Lily, and even Lucinda to stay away from her man. When Ruby asked Lily if she had been another of Simon's rich wives, Simon had to explain to a hurt Lily that he had never planned on marrying her for money, and his love for her had been genuine. He promised not to hurt Lucinda. He then declined Craig's offer to help Craig gain revenge against Lucinda, in exchange for a cut of the profits. Once Simon found out Ruby's plan (working for Lucinda to discredit Simon), he stopped seeing her. Later, Ruby kissed him to annoy Katie, sparking a memorable scene where Katie drenched her with the fire extinguisher. Frustrated by Simon not admitting he loved her, Katie decided he wanted her to be rich like Lily. After pumping the whereabouts of the diamond and Celia's body from Simon, Katie vanished for Simon and Lily's island with Henry, planning on Simon finding her within the next few days because of a note she left. Unbeknownst to her, the note was misplaced and would go unread for weeks.
During Katie's absence, Holden and Luke Snyder were presumed dead in a boat explosion. With Jake McKinnon, Simon uncovered information which hinted they may have survived. Over Lucinda's objections, Simon told Lily, and helped her in her attempts to find her husband and son. Simon then found the note from Katie, but had no money to launch a rescue operation. In exchange for continuing to help Lily, Rose secretly paid Simon with a blank check "borrowed" from Lucinda. On the way to the island, Simon flashed back to Katie's many fights with other women and many declarations of love, realizing, to his horror, he did have feelings for her. Once arriving on the island, he passionately kissed her. She detailed her story of finding the diamond and having it stolen by an eagle and refused to leave until she got the diamond back. In response, Simon tossed her over his shoulder and carried her and her pet rabbit to the plane, leaving Henry behind. In the plane, Katie goaded Simon into admitting a little part of him did love her. Once back in their suite, they were close to finally consummating their marriage when Rose stopped by, begging Simon to go to Lily with Malta. Knowing the danger Lily was putting herself in, Simon agreed. Shortly after he left for the airport, Katie followed, boarding the same plane, and, disguised as a nun, somehow managed to force her way into first class to keep an eye on him!
Once in Malta, Simon (after charming a flight attendant into telling him where Lily planned to stay) met up with Lily, convincing her she'd need his help. That night, Katie barged into their room, mistakenly assuming they were going to have sex. She profusely apologized once she remembered Lily's real reasons for the trip. They agreed that Katie had to stay that night, but would go home tomorrow. She took the floor, Lily slept in the bed, and Simon stood guard outside. Simon overheard the owner of the inn, Signora Cordita, whispering of a plan to move 2 Americans to Argotti. The next morning, he confronted her with the police, but any headway was broken when Katie was arrested for stealing bike tickets. Simon and Lily went to see Katie, who had to go to her hearing. While she was gone, Lily mentioned to Simon how much Katie loved him, and that she wondered who he thought he was fooling when he claimed he didn't care about Katie. Katie, who got off after paying a fine, told them "Argotti" was an opera house. Later that night, all three went to the opera, with Lily eventually going through an escape tunnel she surmised Luke and Holden had used. At the same time, Simon and Katie were captured by Damian Grimaldi's evil half-brother who knocked them out and held them in the dungeon. While trying to take the cross off Katie's neck to help open their chains, they were put into several interesting body positions, and kissed once he freed both from their handcuffs. They then attempted to reopen the tunnel Holden, Luke and Lily had escaped through. Luckily, Simon and Katie were rescued. Though Katie wanted him to return to Oakdale with her, Simon didn't feel right abandoning Lily and sent Katie home alone only to find her kissing another man. Though he realized that Katie was just testing him, he still couldn't find it in himself to tell her how he really felt. That all changed, however, when Katie disappeared. Faced with the prospect of losing her forever, Simon searched frantically for her and when he found her he finally confessed his love and threw Katie her dream wedding.
It was at this time that a dark secret from Simon's past was revealed. After receiving a huge check from the estate of Monique Farrar, Simon became secretive and tried to give the check to charity without Katie knowing. Unfortunately, Katie found out and was surprised when Simon told her that he couldn't use the money because it was tainted. Knowing that he'd have to come clean, Simon told Katie the sordid story of Monique. Apparently Simon married the wealthy Monique years ago just so he could bilk her out of some money. Unfortunately, Monique learned about his past and drunkenly confronted him, kicking him out of the house. The next morning Monique, an excellent sailor, went out on her boat and drowned. What he neglected to tell Katie was that he was the prime suspect in Monique's murder until the prosecutors realized they had no evidence. Though the Farrar family tried to contest her will (she hadn't had time to change it), they were unsuccessful and so the check was his inheritance.
Soon after, Simon learned that Katie's boss, Dahlia, was Monique's sister. Initially believing that Dahlia wanted to seduce him, he was shocked to learn that her true motivation was to get revenge for her sister's death. Not long after an argument with Simon, Dahlia disappeared and foul play was suspected with Simon as the prime suspect. In the course of the next several weeks events starting occurring that painted Simon as a murderer. A few attempts on Katie's life, the death of Dahlia's lawyer and even Simon himself conspired to poison Katie's mind against her husband. However, soon Katie realized that Simon could have killed her at any opportunity and her trust was restored. At this point, suddenly Dahlia showed up! Blaming Simon for her sister's death, Dahlia vowed to kill Simon but he startled her by grabbing the gun and when Katie walked in, she inadvertently shot Simon! Claiming that Simon was trying to rape her, Dahlia told Katie that she and Simon conspired to murder her for her money. Unfortunately, by now Katie's trust in Simon was restored and she refused to believe Dahlia's lies and wrestled with her to get the gun. Luckily Katie was able to get the gun and Dahlia was arrested. Later the Frasiers learned something unsettling: Dahlia murdered her sister!
Simon agreed to help locate Rose and Joe D'Angelo and Paul Ryan in the war-torn country of Avannya with Katie later following to look for him. Upon arriving, Simon was captured and held hostage by a man named Donovan Curry who had himself surgically altered to look like Simon. Fortunately, Donovan was caught before any harm came to Katie and everyone escaped from the island unharmed. Back in Oakdale, Simon opened a detective agency with Katie and Henry Coleman.
Simon was all set to make a happy life for himself when trouble came around in the form of his old "friend" from Australia, Bartleby. An unsavory character, Bartelby threatened to kill Katie unless Simon agreed to carry out a sting for him. Knowing that Bartleby was dangerous enough to carry out the threat, Simon agreed and set out to break Katie's heart so that she'd hate him and not follow him out of Oakdale. Distancing himself from Katie, Simon arranged for her to find him with another woman. Unfortunately, that didn't quite work and so Simon told her that he was suffocating in Oakdale and was going abroad to work on a con. Unfortunately, again Katie caught on and figured out that he was purposely pushing her away because Bartleby was threatening him. Though Simon was perfectly willing to go away with Bartleby to protect Katie, Katie got Bartleby angry by having him arrested. Seeing Bartleby outside the house ready to murder Katie, Simon struggled for the gun and murdered Bartleby in the process. Though now free of Bartleby, Simon remembered his threats that if anything should happen to him, his friends would go after the Frasiers. Afraid that Bartleby's goons would go after Katie, Simon left Oakdale with Henry's help.
Unfortunately, Katie finally learned the truth about Simon's disappearance. Despite pleas from Henry to not look for Simon since her life would be in danger, Katie decided to set out for Australia. Though she initially accepted Mike Kasnoff's offer to go with her, she changed her mind after realizing that he was developing romantic feelings toward her and tried to sneak out of Oakdale without him. However, due to a delay at the airport, she was unsuccessful and, despite her objections, Mike went with her. Unfortunately, upon arriving at the Frasier ranch, the pair was captured by Mordecai, Bartleby's brother, and held hostage. Mordecai, then told them his plan--he was using them as bait to lure Simon out of hiding so that he could get revenge for Simon killing his brother. Though they tried to escape, with Katie even trying to send a message to her sister, Margo, all their attempts were fruitless and finally Mordecai took Katie away to be rescued by Simon. Tied to a chair that had a bomb tied to it, Katie suddenly heard Simon's voice and tried to warn him that it was a trap. Then came Katie's rescuer--but this time, it wasn't Simon; it was Mike! Having freed himself from the basement where they had been held captive, Mike succeeded in untying Katie, but ended up engaging the bomb's timer. Though Katie insisted that they look for Simon, Mike knew they only had a few minutes left and dragged Katie out of the building seconds before the bomb went off! Soon after, Katie was told that the remains of a man were found in the rubble; the DNA was a match for Simon.
Months later, who else but Simon would return to Oakdale alive! Pleading his undying love for Katie, Simon tried to get her to leave with him, but, by now, Katie was engaged to another man: Mike. Telling Katie that he couldn't live without her, Simon warned her that his life was still in danger (a claim substantiated when some goons shot at him and Katie) and he wanted them to go on the run together. Though Katie was confused as to whether to stay in Oakdale or go on the run with Simon, Simon pressured her into giving him an immediate answer since time was of the essence. Having made her decision, Katie went to Mike to tell him she loved him and then set out to leave with Simon. Hiding out at the docks, before setting out to leave everything behind, Simon confessed that he set up the gunfire incident in order to prove that the danger was real. Even though Simon's feelings for Katie hadn't changed, it was clear that Katie wasn't the same person Simon left behind, yet she was determined to stick by her husband. Even thought Katie agreed to leave town with Simon, she was still confused and conflicted about leaving her life in Oakdale for life on the run with Simon.
Finally, after a spending the night in the train car talking with Simon and making love to her husband, Katie was convinced that she had made the right choice even after Simon's contact, who was suppose to get them out of the country, was killed. Meanwhile, Katie thought she had convinced Mike to help get them out of the country, but instead he plotted behind her back and convinced Simon to leave Katie behind in Oakdale for her own protection. Once Katie realized she'd been duped, she followed Simon to the dock where they shared a tearful goodbye through the locked fence before he disappeared into the fog. Months later, Simon returned to rescue Katie from a mental hospital, after seeing Henry's ad in "Soldiers of Fortune" magazine. After successfully rescuing Katie (who'd been committed following an "attack" on Pilar Domingo), Simon informed her that he'd turned informant in Australia and was no longer in danger. He then asked her to go away with him and settle down for a new life in Australia. However, unbeknownst to others, Simon had a connection to another Oakdale citizen--Pilar Domingo!
It was Simon who found Mike’s old lover in Spain and paid her to lure Mike away from Katie. Unfortunately, the plan didn't go as expected since Katie suspected that Pilar was shady from day one. While Simon (who never suspected that Pilar would go after Katie) was getting what he wanted, Pilar was left in the lurch since Mike no longer trusted her and wanted nothing to do with her. Angry that Katie ruined everything for him, a truly demented Pilar decided to get even by murdering her. Although Henry insisted that the police be called, Simon was against it since he figured Pilar would panic. Luckily, Henry called Mike who called Pilar's cell phone. Pilar answered and overconfidently gave a clue to her location--it was near Mike's house. Mike's arrival was all the distraction Katie needed to wrap Pilar in a fisherman's net as a means to get away. Unfortunately for Pilar, Katie's efforts caused her to fall on her own knife. The ordeal over, Simon surprised Katie by announcing that there was no rush to go to Australia. Confused by Simon's sudden change of heart, which coincidentally occurred after Pilar's death, Katie, remembering Pilar's taunting about Simon at the boathouse, asked him if there was indeed a connection. Although he tried to deny it, when Katie found a note to Simon from Pilar (written just before she kidnapped Katie), Simon was forced to confess that he met Pilar in Spain and hired to keep Mike away from Katie. Upset that Simon introduced Pilar into her life, Katie told him that their marriage was over since she could no longer trust him. After a heartbreaking goodbye, Simon left Oakdale without Katie.
A few years later, while Simon was on a cruise with a wealthy woman named Vienna Hyatt, none other than Mike and Katie would end up in the cabin next door. Upon seeing Katie, Simon ducked out and later secretly approached her by pretending to be her masseuse. When he revealed himself, Katie accused him of following her but he explained that his presence was just a coincidence. Katie wasn't quite sure if she believed that and warned Simon to stay away from her and Mike, who were on their honeymoon. Unfortunately, Simon didn't listen and approached Mike and Katie at dinner, earning a punch from Mike in the process. That same night, alone in a bar with Katie, Simon tried to soften Katie up by apologizing and telling her that he never got over her. Unfortunately, Katie remained cold and told Simon she was in love with Mike. Later, while the waters were rocky, Simon and Katie met up again on the deck. Simon's flirtations rankled Katie and she insisted that he leave her alone. Then she tumbled overboard! Simon rushed to save her and they both drifted to shore on a life preserver. The next day, the pair found themselves alone on a deserted island, just like the old days. It didn't take long, though for Simon to learn that the island wasn't so deserted--there was a golf resort on the other side. However, Simon was hoping to rekindle old feelings and kept this a secret. Unfortunately, about a day later, Mike rescued the paired and exposed Simon's deception. Mike and Katie returned to Oakdale, and with nothing better to do, Simon followed. Though Katie was certain he was there to either break up her marriage or con some woman out of her money, Simon denied it. He also surprised her by stating that he struck oil in Australia and was now a very wealthy man. Soon after, Simon decided to set up roots by purchasing an old hotel. Hoping to have it renovated, Simon overheard fledgling interior decorator Carly Tenney trying to secure a loan. When she was rejected, Simon approached her about working for him. Although she was wary, since Simon’s reputation had preceded him, Carly decided that she needed the money and took him up on his offer.
Unfortunately, Simon's funding fell through and he was forced to go to a loan shark for money. When the loan shark put pressure on Simon to pay, he and Carly decided to pull an elaborate jewel heist on Vienna. Though they were successful, Katie (with whom Simon had a one-night stand) became suspicious and blew the whistle on the pair. Carly and Simon then went on the run to evade the police. Months later, Carly returned while Simon remained on the lam. At Carly's request, he sent the jewels back to their rightful owner so that the charges against her would be dropped.
Years later, Simon returned to Oakdale after Jack and Carly unexpectedly foiled an art heist that Simon was planning in New York. Simon got a job at Al's and declined to run a scam with Clarissa when, on a date with the newly widowed Katie, he remembered that being poor with Katie had been fun. Henry convinced Clarissa that he could substitute for Simon in her real estate scam. However, Barbara inadvertently foiled the scheme, and Katie and Simon, pretending to be undercover officers, "arrested" Henry and Clarissa to save them from real jail time. Katie decided that she needed to start her life over in New York, and she asked Simon to go with her. Unfortunately, Katie had a baby to think about and quickly realized that she couldn't raise her son as a drifter. Realizing that Simon wouldn't truly be happy with a normal life in Oakdale, Katie asked Simon to leave.