The ambitious Craig Montgomery fell for Betsy Stewart whom he met at Oakdale University. At the time, Betsy was hurting from a relationship with Steve Andropolous--a relationship Betsy ended because it caused Steve's brother (who wanted Steve to stay away from Betsy) to have a fatal heart attack. Realizing that Betsy was in still love with Steve, Craig tried to undermine Steve's position at McColl's Materials, where Craig worked as well, and fed on Betsy's guilt over Nick's heart death. Finally, it seemed as though there was only one way to get Betsy to forget about Steve--he had to die. To accomplish this, he arranged for Steve's truck to explode. Unfortunately, Betsy happened by instead of Steve and Craig rushed out to save her from the explosion. Soon after, a grateful Betsy accepted Craig's marriage proposal. Betsy and Craig's wedding kicked off 1983. When they returned from their honeymoon, Craig and Betsy put on a happy facade for their friends and relatives, but the truth was that Craig was impotent due to residual nerve damage from the truck explosion. An out-of-town doctor informed Craig that the impotence might be temporary, but the sterility was not. Craig didn't tell Betsy he was sterile; instead, he said his impotence was caused by the knowledge that she was in love with Steve. Betsy was appalled by the accusation and by Craig's jealous fits over Steve and took her stepmom, Kim, up on her offer to get away and stay with a friend in Ronda, Spain. Meanwhile, Diana McColl, the daughter of Craig's boss, Whit McColl, flew in from Paris. One look at this gorgeous blonde and Craig realized his potency was returning. Diana McColl insinuated herself further in this romantic quadrangle by coming on to Steve. When he snubbed her, she let it slip out to Craig that Steve had borrowed money for a plane ticket to Spain. Craig realized Betsy and Steve had been together and was crushed. One day, while Betsy was out, Craig took a call from her doctor and was stunned to learn that she was pregnant! Although Craig had regained his potency, he knew he was still sterile, which meant Betsy was carrying Steve's child!

The surprise birthday party for Whit provided the perfect setting for Craig to exact revenge on Steve. Craig contacted con man Ike Slattery, who, posing as Steve, stole some rare coins from Whit's collection while the party was in full swing and planted one in Steve's apartment. When Whit discovered his coins were missing, Craig convinced him that Steve was the culprit, and when the police searched Steve's apartment, they found one of the coins. Confronted by the cops, Steve bolted, and the police opened fire. Steve was hit in the leg but managed to escape. A grateful Whit promoted Craig to vice president at the factory. Meanwhile, Craig and Diana made plans to open a nightclub on the Stenbeck yacht, which Whit had bought as a present for Diana. The club was to be called the Anemone. Betsy wasn't pleased since they were already building a house in expensive Ruxton Hills, so where was all this money coming from? Meanwhile, unbeknownst to Craig, Betsy was helping Steve, who was on the run from the law. At one point, she told Craig that her doctor had recommended she take a cruise, and he believed her. Actually, Craig was relieved, because now he could spend more time with Diana. However, when Betsy told Craig that she was going to call her broker and sell some stocks to get money for the cruise, Craig panicked. He had made some bad investments and had lost all her money in the stock market!

The Montgomerys were broke, only Betsy didn't know it yet. Suddenly, Craig remembered the cash receipts from the Anemone. With them, he was able to give his broker the money he'd put up to cover him. He also found out that Ike Slattery had sold a coin to Vermeil (whom Betsy and Steve had already figured out was involved), and was headed for Bermuda. What a happy coincidence that Betsy was on the same boat! Craig made plans to join the ship in Nassau, with the intention of selling his own coin to Vermeil. Luckily, Steve and Betsy found out about Craig's arrival beforehand, and Betsy pretended to have a happy reunion with her husband. Being careful to conceal his identity, Craig met with Vermeil, who offered him a measly $10,000 for the coin. Craig tried to negotiate, but the crafty coin dealer held firm. When Steve got wind of Craig's attempted deal, he informed the captain there was a stolen coin on board and contacted the police in Bermuda. To avoid being caught, Vermeil was forced to throw the coins overboard. Seeing Betsy and Steve together, Craig made plans to return to Oakdale without Betsy. By this time, Vermeil knew Steve was on to him and was busily plotting his ruin. Unaware that Vermeil was on to him, Steve decided to infiltrate his organization in hopes of finding out who set him up. He was in luck when Ike Slattery, the man Craig hired for the job, showed up. As Steve and Betsy bid each other a sad goodbye in Bermuda, Craig was proposing to Diana in Oakdale. Diana, however, didn't love Craig -- she loved Steve. When she arrived home, Betsy told Craig that she was leaving him.

Soon after, Betsy gave birth to a healthy daughter. In remembrance of her father Dan, she named the child Danielle. Craig told his wife how much he loved her, and now that they had a child, he hoped things would be all right between them. The night, Vermeil ordered his security people to find Steve and kill him! Diana helped Steve escape by hiding him in her room, and he rushed back to Memorial just as Betsy took a brief turn for the worse. Craig spotted him, though, and had his rival arrested. However, Craig's sister, Margo, out-smarted him and got Ike Slattery to give her enough information to free Steve. After all was said and done, Betsy told Craig she still planned to leave him for Steve. Meanwhile, Whit figured out the only two people who knew the combination to his safe were Lisa and Craig. He confronted Craig, who was unable to lie out of it, and Whit fired him. Then there was the question of who had embezzled funds from the nightclub. When Diana didn't buy his excuses, Craig pleaded poverty. Diana said she wouldn't call the police if he handed over his half of the club to her. Craig told Betsy he had been fired because Whit said he spent too much time with the baby, and Betsy bought the story. Betsy was moved when she heard Craig talking to his sleeping daughter about his losses, and weakly told Steve she couldn't leave Craig just yet. At the end of 1983, Craig found the note Betsy had written to Steve telling him how much she loved him. He quickly tore it up and forged a new one saying Betsy loved Craig and regretted having to betray him. Ever the schemer, Craig found a new way to hold on to Betsy: He signed up for stunt school because he wanted to learn how to fall down stairs. When Betsy arrived to get the rest of her things, Craig picked a fight with her and "fell" down the stairs. Craig then cried "paralysis," getting Betsy to move back in with him. Certain that Craig was faking, Steve brought in his ex-cop cousin Frank Andropoulos to investigate the slippery Mr. Montgomery.

Meanwhile, a major storm ushered in the New Year. After it had passed, Betsy's boathouse was on shaky ground. Not about to give up on doing Steve in and, knowing that he was already scheduled to work on the boathouse, Craig loosened a support beam so that it would fall on Steve's head. Unfortunately, Steve and Betsy had decided to work together to salvage their special place, and the beam landed on Betsy instead. Luckily, Steve was able to save her from the wreckage. With the boathouse now destroyed, Craig knew he was sitting on valuable lakefront property. He located a Colonel Jameson, who eyed the property as a potential site for a chemical plant. Jameson shrewdly promised Craig a top level-job if he were able to talk Betsy into selling it. However, Betsy had other ideas. She surprised Craig by telling him she planned to build a home for abandoned children on the lot and call it the Refuge. Steve's construction company put in a bid. Diana heard about Steve's plans, got hold of the other bids and changed them, making Steve's the lowest. Steve and Tucker's company got the job. One night, when Betsy couldn't go through with a romantic evening, Craig left in disgust. Afterwards, Diana saw Steve and Betsy kissing and was quick to inform Craig. Diana was also suspicious that Craig was faking his paralysis. She threw a cup of tea in his lap, and when Craig jumped up, she knew he could really walk and threatened to tell Steve.

At the same time, Steve and Frank got Craig's address book and found the number of the stunt school. The instructor confirmed that Craig had come to the school to learn how to fall down a flight of stairs. Steve paid Craig a visit and implied that he had damaging evidence against him. Then he put an envelope on the mantel and left. Betsy arrived home and almost caught Craig getting out of his wheelchair to get the envelope. Craig accused Betsy of getting love letters from Steve and threw envelope in the fire. As gently as possible, Betsy told Craig their marriage was over. Then she went upstairs to pack and discovered that Danielle was gone! Craig said he couldn't let Betsy take her away, so he hid her. Craig threatened to leave town with Danielle if Betsy called the police, and if she went to Steve, she'd never see her daughter again. Up to this point, Craig's mom, Lyla, had sympathized with Craig. However, once Craig used his own child, Lyla realized how twisted her son was. Out of guilt, she traced Danielle to the home of Mrs. Hoffman, a maid whom Betsy had fired previously, and Danielle was returned to her mother. Meanwhile, Diana finally confessed to Steve that she knew Craig was faking his paralysis. It wasn't until Lyla lashed out at him, that he realized how sick he had become and he turned himself in to the police and was sentenced to 5 years in a halfway house. Craig was granted an early release when his family became concerned by the way his psychiatrist (who was brainwashing Craig) kept him isolated from everyone.

After his release, Craig was determined to make up for all the pain he caused and he forged a friendship with Betsy. At this point he started working for Lucinda Walsh. One of Craig's first duties at Walsh was to travel to Montega and rescue Lucinda's goddaughter, Sierra Estaban, from Montegan terrorists after Sierra's father, the country's ruler, Jacabo Estaban, was overthrown. In Montega, Craig soon met a boy named Carlos burying Estaban. Soon, the pair found them beset by a wave of bullets and escaped. That day, Carlos removed his hat and Craig was shocked to see that this wasn't a teenage boy, but a young woman--Sierra! After meeting up with Jacabo's former general, who gave Sierra an emerald earring which he said belonged to the mother she never knew. Craig and Sierra were able to escape to Oakdale. While Sierra was trying to get settled in Oakdale, Craig ended up being the hero when he saved Betsy from the obsessive, demented Russ Elliot. In the meantime, Craig found himself falling in love with Sierra and he decided to help her search for her long-lost mother. Certain that Lucinda knew something about Sierra's mother, since she was unusually soft toward the girl, Craig did some investigating and discovered a faded picture. Confronted, Lucinda told Craig and Sierra that Sierra's mother was her friend, Mary Ellen Walters, who died years ago of a sudden illness. Doing some more digging, Craig discovered that Lucinda herself was Mary Ellen! Craig confronted his boss and agreed to keep her secret.

However, later, Craig decided that he wanted to marry Sierra and felt that he couldn't do that unless he was honest with her. However, by the time Craig decided to be honest with Sierra, she had already learned the truth about Lucinda. Hurt that he kept it from her, Sierra ran off with another man, Tonio Reyes. Although he tried to find comfort with Iva Snyder, Craig just couldn't keep his mind off Sierra. At the same time, Sierra wasn't happy in her new marriage and when Craig informed her that Tonio was having an affair, she had an affair with Craig. Sierra then became pregnant and finally decided to divorce Tonio. When Sierra's son was born, she and Craig (who had had surgery to correct his sterility) were elated to learn that Bryant was Craig's son and they married in her hospital room.

Later, tragedy struck. When flying to Greece to help Betsy find Steve, Craig's plane went down and he was taken hostage by a Greek criminal. After almost a year, Craig was rescued by his family and returned to Oakdale only to learn that Sierra had disappeared in Montega and was presumed dead. Heartbroken, Craig tried to go on with life and began a relationship with Iva's younger sister, his employee, Ellie Snyder. However, Ellie had a rival in Emily Stewart, who wasted no time looking into Ellie's past and discovered that Ellie was no naďve farm girl; she had secretly gotten married and divorced in Chicago and then starting seeing a married man. Ellie found out however that Emily was looking into her seedy past and confessed the details to Craig. Craig understood and continued dating her. However, when he got a lead that Sierra was alive in Montega, he left town in the hopes of finding her. He was successful and, after the resistance was squashed, Craig and Sierra were able to reconcile and they moved to Miami so that Sierra could be close to Montega but their family would be safe from any terrorist attacks. Craig briefly returned in 1990 and helped clear Ellie, who was being held under suspicion of murdering Brock Lombard; because he had proof of Ellie's whereabouts at the time of Brock's murder. Apparently, on the date Brock was murdered, January 15, 1990, Ellie placed an overseas phone call to Craig to discuss her concerns about her involvement with the Lombard family. Later, in 1991, Sierra gave birth to another child, Lucinda "Lucy" Montgomery. Years later, Craig briefly returned to Oakdale after some marital problems with Sierra, and got involved with Lucinda's newly discovered sister, Samantha, and Emily again. However, in the end he realized he loved his wife and returned to his family.

Unfortunately, Craig eventually grew restless and left Sierra so that he could travel the world. On a business trip to Hong Kong, Craig met Carly Tenney who begged him to rescue her from her husband (and Craig's business associate) Winston Lowe. Having reverted back to his opportunistic ways, Craig refused to help her unless there was something in it for him, and when she agreed to retrieve a prototype from Lowe's office he agreed to help her. In the end, Lowe died of a heart attack. Afterwards, Craig returned to Oakdale to repair his relationship with his estranged son. However, connecting with Bryant wasn't Craig's only motive for returning to town. Apparently, his business dealings left him low on funds. After his business deal with Carly fell through, Craig "borrowed" from Bryant's trust fund to cover his debts. Unfortunately, Lucinda found out and confronted him. Knowing that she had no real proof, Craig kept Lucinda at bay by having her drugged to appear incompetent. Later, while reacquainting himself with Barbara Ryan Munson, Craig quickly saw her as his meal ticket and seduced her into marrying him. With Barbara's money, Craig was not only able to repay the money he took from Bryant's trust fund, but was also able get stock in Worldwide. Now financially secure Craig was on top of the world when suddenly Barbara was injured a bombing. Though not overly concerned for a woman he didn't love, he was surprised when he was arrested for the bombing. Craig maintained his innocence, yet all the evidence pointed to him. Only an investigation by Hal Munson and Emily kept him from going to jail.

A free man once again, Craig put his energies into wooing Carly away from Jack Snyder. Though Carly denied having any romantic feelings for him, it was clear to Craig that she was in fact very interested in him. Though Carly softened towards Craig after Bryant's tragic death in a car accident, she was still devoted to Jack Snyder. That was until Jack's ex-wife, Julia tried to murder her. Believing she'd be better off without Jack, Carly turned to Craig and the pair made love. Then around Christmas, Carly suddenly disappeared without a trace! Determined to find the woman he loved, Craig made a nuisance of himself with the Oakdale PD trying to find her. Though with his help, the police were able to figure out that Carly was shipped out of the country in a coffin, there still was no clue as to where the coffin went. Though he wanted to charge off and find Carly on his own once Rose returned from Belgium, he was persuaded by Lucy to remain in town. Though he'd hoped to be Carly's savior by rescuing her, the Oakdale PD didn't exactly appreciate his frequent visits to get information. Told repeatedly to leave police work to the police, Craig decided to work on James Stenbeck himself and, deducing that he was faking his coma, made a deal: he'd help James escape if he would release Carly and Emily.

Unfortunately, James double-crossed Craig who was forced to stand by and watch Jack be Carly's rescuer. Later, Craig was shocked at the sight of the disfigured Carly who arrived in Oakdale. Repulsed by her appearance and disgusted at his reaction, Craig sought comfort in the arms of Carly's sister, Rosanna. Finding in Rosanna a kindred spirit, the two began a relationship. Complicating matters though was Craig's attraction to Carly (who had surgery to correct the disfigurement) as well as Rosanna's attraction to Mike Kasnoff. In addition to his complicated relationship with Carly and Rosanna, Craig also had to deal with Lucy's romance with Aaron Snyder. Still pining for an engaged Carly, Craig's friendship with Rosanna continued to grow until something surprising happened. His attraction to Carly changed into a deep friendship and his friendship with Rosanna blossomed into love.

Unfortunately, Craig and Rosanna's relationship was constantly under strain due to her insecurity about Carly. Knowing that a now-pregnant Carly was under orders to avoid stress, Rosanna hired Barbara to replace her at Monte Carlo, something that Craig was against. Complicating matters was Jack who was against Carly working during the pregnancy. Finally, to ensure that Carly was Monte Carlo's top designer, Craig masterminded a plan with Barbara's former victims to have her kidnapped until Carly could finish the designs. Unfortunately, Barbara escaped custody and turned up at Fairwinds just as Craig and Rosanna were finished saying their wedding vows! Despite this revelation, it was Craig who ended up leaving Rosanna when he found out she'd gone behind his back and let Aaron see Lucy. Though Craig later went back to Rosanna, this time it was she who felt betrayed and refused to help him when he was arrested for the kidnapping. Craig's salvation came in the form of Barbara who agreed to drop charges if Craig would sell Monte Carlo to her for $ 1.

Not one to stay down for long, Craig saw an opportunity to get back into business by buying Java Underground with Dusty Donovan as a partner. Though Rosanna initially refused to finance Craig's venture because of Dusty's less than stellar reputation, she later relented. At the same time, a barren Rosanna's maternal instincts were kicking in and she announced that she wanted a child. Wanting to make Rosanna happy, Craig agreed to adopt but told Margo that he really didn't want a child. Afraid of losing a child the way he lost Bryant, Craig decided to sabotage their chances at adoption. Knowing that agencies were reluctant to place a child with him due to his prior criminal record, when Craig learned that Dusty had been using their club in an illegal gambling operation, he anonymously called the police. Though his plan succeeded, Rosanna learned the truth and was ready to leave him. Desperate to hold on to his wife, Craig got a very speedy adoption and surprised Rosanna with their son, Cabot. It didn't take long, however, for Craig to suspect that something was wrong with the adoption, especially after the woman who arranged the adoption, Annabelle Fettle, failed to provide adequate medical history on the baby (in fact, the medical history was scribbled down on a piece of paper right in front of Craig). After being assured by Annabelle that Cabot's birth mother knowingly gave up the child, Craig turned a blind eye and kept quiet. However, the walls started closing in, weeks later, when Canadian authorities starting asking questions about the baby broker, Annabelle.

To Craig's horror, Annabelle went to Craig and demanded that he hide her from the authorities, or she'd spill that Cabot's adoption was illegal. While under enormous pressure to keep the police from finding Annabelle, Craig also had to deal with Rosanna's friendship with Paul Ryan. Very jealous, Craig saw Paul as a threat and wound up framing him for the murder of Rose D'Angelo, of which Paul was a suspect. Unfortunately, that event would lead to Craig's downfall. Needing help with Annabelle, Craig enlisted his partner, Molly McKinnon who was willing to help him for a price--he had to convince an angry Dusty to let Molly remain a partner at Metro. However, despite his promise, Craig knew the attempt was futile and didn't even try to talk Dusty out of kicking Molly out. Later, an angry Molly called Craig and argued about their deal, with Paul overhearing about the illegal adoption! When confronted, Molly spilled all to Paul, who in retaliation, alerted the police. In one swoop, the Canadian authorities arrested Annabelle, returned Cabot to his natural mother, and Rosanna left Craig and Oakdale.

Unfortunately for Craig, Rosanna wasn't the only one whose respect he lost. When Lucy found out about the illegal adoption, she moved out of Fairwinds despite Craig's many pleas for her to stay. Months later, Rosanna served Craig with divorce papers, letting him off easy by letting him keep his money and Metro. Although Craig wanted to fight the divorce, Rosanna warned him that if he fought it, she'd take everything away from him. Seeing no other choice, Craig signed the papers. Later, in a desperate attempt to get Rosanna back, Craig kidnapped Cabot away from the woman taking care of him in Las Vegas. Unfortunately for Craig, he was knocked out by the baby nurse. In the scuffle, the baby nurse was knocked out as well and a fire ensued, endangering Cabot! Luckily, Paul happened along and rescued Cabot, endearing himself to Rosanna. The same day, Rosanna married a stranger named Jordan Sinclair in an attempt to gain custody of Cabot, since a mysterious emissary was demanding it. In the fallout of Craig's kidnapping attempt, a furious Rosanna (who now had custody of Cabot) threw him out of Fairwinds! Left with nothing, Craig again turned to Lucy for support, but, like before, she turned away and this time made plans to go to Montega for the summer. Having lost everything, including Lucy's respect, Craig sunk into despair, living in back of his club "Metro" and drinking.

Although Craig begged her to stay, Lucy refused to stay and watch her father self-destruct. Suddenly, the day she was scheduled to leave, Lucy was kidnapped! Although it was believed that she was kidnapped by Dusty, in reality, Dusty had kept her from being kidnapped. Hiding out with Lucy, who had been the victim of some near kidnappings just prior to this, Dusty investigated and learned that the man going after her was named Don Creel. After weeks of hiding out, Dusty was located by the police and told them his theory that someone in Lucy's family had tried to have her kidnapped. It turned out that Dusty was right. Upon learning Dusty's theory, Craig subtly cast suspicion on Sierra's new husband, Alan Drake, and then met with the men he had hired to kidnap Lucy. His entire plan derailed, the plan being that he "rescue" Lucy from the kidnappers, thus earning her love back, Craig alerted the would be kidnappers that the police were on to them and refused to give them their money. However, Creel wouldn't leave Craig alone and kept demanding his money. Finally, one day, Craig met with Creel, and, after a confrontation, he shot him! Although the dying man was almost able to implicate Craig, Craig again covered his tracks by implicating Alan. Not long after, Craig tried to arrange for Lucy to be kidnapped again, this time to keep her from Dusty.

Unfortunately, things went horribly wrong. Alan was set to give the kidnapper, Wade Carlson, the ransom money, but came armed. Just then, Craig happened upon the scene and Wade confessed that Craig arranged the kidnapping! Alan then held the gun on Craig, but he resisted, accidentally shooting Alan! In the meantime, Wade himself went ballistic and shot Craig! He then tried to take Lily Snyder (who had followed behind) hostage. Luckily, Craig was able to rescue her. Although Alan survived to make it to the hospital, and to whisper Craig's name to Sierra, he died before he was able to talk to the police. Immediately after, Sierra, who always refused to believe that Alan was guilty, realized that it was Craig who set up the kidnapping. Approaching Dusty with her theory, they both set out to get the evidence. Dusty got it and gave it to Lucy. However, to everyone's shock, Lucy, though disappointed in what her father had done, refused to give the evidence to the police. Despite this, Lucy was unwilling to forgive Craig for what he'd done and shunned any contact from him. Although Craig looked to Lucinda to help him get through to Lucy, Craig lost any shred of credibility that he might have had with her and she refused to help him.

In the meantime, to Craig's annoyance, Lucy was entering into a relationship with Dusty. Learning that Dusty was sponsoring a fight with a shady character named Dom, Craig tried getting information about the fight. Unfortunately, his questions only served to annoy Dom who warned Dusty to keep Craig quiet. Craig's chance to get Lucy away from Dusty came with the arrival of an old childhood friend of Lucy's, Rafi Ortega. Seeing that Lucy and Rafi still had a connection, Craig tried to push things along by giving Rafi a childhood photo of Rafi and Lucy (to show to Lucy) and telling Rafi that Dusty had a jealous streak. Finally, Craig got his chance to show Lucy what kind of man Dusty was when he discovered that the fight Dusty was helping to sponsor was fixed. Craig wasted no time telling Lucy who refused to believe him at first, until she and Craig were both held at gunpoint by thugs connected to Dom who was the mastermind behind the fight. Luckily, Craig and Lucy were able to escape and in the aftermath, Dom was arrested. A few weeks later, Craig was kidnapped and whisked away to a monastery! At the monastery, a monk named Brother Francis showed Craig photos and urged him to repent. He urged Craig to reflect on his past but just as he was about to, Craig saw a chance to escape and took it. Unfortunately, the attempt failed. When Craig tried to bargain with the monk, Brother Francis insisted that Craig would be released only when he proved that he had truly changed. He then left Craig with photographs of Cabot, Lucy, Bryant, and Sierra, and asked him to own up to the impact he'd had on their lives. Alone in his cell, Craig broke down and then discovered something startling--a camera; someone was watching him! Knowing this was all a set up, Craig feigned redemption for the camera yet vowed to get even with whoever had him locked away. A few weeks later Craig was rescued by Margo. Although he discovered that Sierra was his kidnapper, he kept mum and attempted to reign in his destructive tendencies. His efforts didn't go unnoticed by Sierra and she rewarded him by offering him a job at Worldwide, as owner of Jennifer Munson's company "Street Jeans."

Though Craig and Jennifer clashed, the pair impulsively fell into bed together. A horrified Jennifer just wanted to forget the entire incident, but Craig didn't make it easy by blackmailing her—he would only keep quiet about her affair if she stayed at Street Jeans. Jennifer, though, countered by revealing the truth anyway. Weeks later, Craig accidentally learned from Katie that Jen was pregnant. Because of the time of conception, he knew he had to be the father. Craig was determined to be a part of this child's life and made that fact perfectly clear to Jennifer, despite her protests. Unwilling to let a man such as Craig be in her child's life, others (including Margo) came up with a plan to run him out of town by framing him for drug possession. As expected, Craig left the country and ended up in Bangkok where he met up with a familiar face--Rosanna. Rosanna revealed to him that the presumed-dead Cabot (whom she gotten back) was alive and that James made her his prisoner when he caught her trying to escape from marrying him. Craig promised to help her get her baby back. However, Rosanna quickly discovered it was hopeless to protect Cabot from James herself and gave the child away so he'd be safe. Soon after, Craig found out there was no warrant out for his arrest and returned to Oakdale. Meanwhile, Craig met with attorney Jessica Griffin to find out what he needed to do to get partial custody of the baby. Jessica pointed out that Craig needed to show that he was a responsible adult and Craig realized that he should get married. After getting Margo to write a letter of recommendation stating that he'd be a good father, Craig convinced Rosanna to marry him so they could get custody of his baby. Unfortunately, that decision would lead to tragedy.

Shortly after, Rosanna met a high school student named Gwen Norbeck who was pregnant and looking to give her baby up for adoption. Touched by the girl's plight, and wanting a family, Rosanna arranged to adopt the child when it was born, against Craig's wishes since he was more concerned about his own baby. Later, in a strange turn of events, both Jennifer and Gwen went into premature labor at the same time! After hours of fighting for their lives, Jennifer's baby apparently died. However, to Rosanna's confusion, Craig was showing no grief over the loss of his own baby. Although she tried to talk to him about the loss of his child, he refused to give a suitable explanation, simply stating that he was willing to give his heart to his adoptive baby. Rosanna became even more confused when Craig started taking such an interest in the baby, calling him "his" baby. Considering that Craig had been against the adoption, his attachment to the child so soon didn't make any sense. Remembering that Craig had been hanging around the hospital near both babies, Rosanna came to a startling conclusion—Craig must have switched the babies!

To see if her hypothesis was correct, Rosanna got the baby's footprint records and matched them up with the baby's foot-—they didn't match. Horrified, she confronted Craig who confirmed that he did indeed switch the babies—only because he wanted to be able to raise his own child. Although Craig tried to make excuses for what he'd done, a sickened Rosanna refused to listen and ran out, with the intent of going to the police. Craig followed her, intent on stopping her. Desperate to get Rosanna to stop and listen to him, Craig hit her car continually from the side. Tragically, that caused Rosanna's car to crash. Although she awoke just enough to tell Paul "wrong foot", Rosanna slipped into a coma and never woke up. In the aftermath, Craig was sent to jail for attempted murder and the baby was placed in Carly's custody. Four months later, after a bitter custody battle between Carly and Gwen, as well as Jen's drug addiction, the truth would finally be revealed.

Fresh from having had his conviction overturned, a year later, Craig returned, hell bent on getting custody of his son. At the same time, he became a thorn in Paul's side again—by offering to make Emily full partner in the paper (thus ensuring her loyalty to him) and by flirting with Paul's fiancée, Meg. Meanwhile, with help from his attorney, Tom, it seemed as if Craig might have a shot when he was awarded visitation rights. Dusty's only hope was for Craig to be in jail again. To accomplish this, Dusty asked Lucy to bring Craig up on kidnapping charges. Though Craig begged her not to turn against him, Lucy knew that Craig was not fit to raise a child and was determined to testify about his kidnapping of her years earlier. Unfortunately, Craig got to Lucy when Dusty's brakes failed. Though it couldn't be proven, everyone suspected that Craig had tampered with them. The day of the trial, Craig played on Lucy's fears that if she were to testify, something awful might happen to Dusty. Fearing for Dusty's life, Lucy stated in court that she could not be absolutely certain that it was Craig who kidnapped her. Determined to get Craig away from Johnny, Dusty was decided to do whatever it took to get him out of Johnny's life and showed Lucy his gun. After telling Emily, Lucy warned Craig to back off but he refused.

During the conversation, Dusty called Craig to meet with him. Knowing what was being planned, Lucy rushed out to stop him. Although she was able to knock Dusty down, Craig was shot anyway. While Dusty was in jail for attempted murder, Craig recovered and told Lucy of his plans to get custody of his son, Craig Jr. and keep him away from his family. Realizing that the fighting would never end, Lucy decided the only way to protect Johnny and let him have a happy life was to spirit him away from Oakdale. Soon after, Craig manipulated Lily in order to get an "in" at Worldwide. Drawing on their long friendship, Craig offered to help Lily with a business deal with a baby food company she was negotiating. He not only helped to seal the deal, but also helped settle a potentially nasty court battle when the baby food was contaminated. Since Lily was out to prove her worth to her mother, which Craig capitalized on, all this was done in secret and Craig got Lily to sign over WorldWide to him.

Since he rushed Lily, she had no idea what she signed until it was too late. Craig then offered to return the company to Lucinda in exchange for Lucy and Johnny's whereabouts but Lucinda steadfastly refused. Later, Paul claimed to have visions of Johnny and said that he'd reveal his whereabouts if Craig returned Worldwide. Craig didn't take the bait. At the same time, Paul's engagement to Meg apparently unraveled. Meg ran to warn Craig that Paul was unhinged. Her relationship with Paul over, Meg spent more and more time with Craig. Craig seemed to soften around her and finally kissed her. Meanwhile, Craig was shocked to see a picture of Rosanna smashed in his house and wondered if Rosanna was there. His call to the clinic confirmed that she had disappeared. Suddenly, Craig began having vague visions of Rosanna and started hearing her voice. Finally, he received a phone call from her. However, it didn't take long to realize that the person on the other line was not Rosanna. Apparently, he'd been set up by Paul and Lucinda.

Later, Craig collapsed after being poisoned. Luckily, Meg found him and took him to Memorial. Though he knew Lucinda must have done it, Craig told everyone it was an accidental overdose since he wanted to exact his own revenge. In the meantime, Craig was getting closer and closer to Meg and he offered to return WorldWide if she married him. After a quick but lavish wedding, Craig whisked Meg off to a honeymoon in Vancouver. There, he confronted her with his knowledge that she never broke things off with Paul. He quickly realized that she'd been plotting with Paul the whole time. After drugging Meg, Craig sent a text message to Paul (as Meg) asking to meet him at the cliff. When Paul arrived, Craig confronted him with a gun. Suddenly, Paul lunged at him and, in the scuffle, Paul slipped off the cliff. Craig tried to save him but lost his grip and Paul seemingly fell to his death.

Seeing Meg's devastation, Craig paid for a search but Paul was nowhere to be found. Afterwards, Craig gave Worldwide to Meg and told her she could do whatever she wanted. He also agreed to her request for an annulment. Finally, Meg decided that maybe Lucinda wasn't the best choice to head the company after all and decided to head it herself hoping that she could make some good out of it. As Craig showed Meg the ropes about running the business, Meg started seeing a softer side to him and decided to stay with him. Later, Craig confessed to Meg that he loved her and wanted to build a life with her. Soon after, Paul returned to town with none other than Rosanna. Hurt that Meg seemed to be enjoying her cushy life with Craig, Paul rejected her. Craig assured Meg that although Paul may not want her, he did and, later, the pair finally made love. At the same time, Craig realized that Rosanna had no memory of the crash or the baby switch. Eventually, Rosanna's entire memory came back and she told Craig that she would reveal his part in the baby switch. However, Craig warned her that with him in jail, Meg and Paul (who had just asked Rosanna to marry him) would surely reunite. Not wanting to lose Paul, Rosanna lied on the stand that she had no memory of what happened. Later, Rosanna urged Craig to get Meg pregnant to solidify their marriage. Soon, Meg became pregnant. Weeks later, Meg's doctor informed her that her baby had inherited a genetic disease from his parents. Confused since this specific diseased had never shown up before on tests, Craig looked into the matter and got a doctor to admit that not only had Meg ordered a paternity test for her baby---Rosanna had altered it. That meant that Paul, not Craig, was the father of Meg's baby.

A furious Craig went to Rosanna who confirmed the truth—Paul was the father. Craig vowed revenge on Paul but Rosanna convinced him that the best revenge would be raising Paul's son in secret. Though he agreed, Craig could not get the horrible thought that this child belonged to his worst enemy out of his head. Craig became cold and almost seemed repulsed by the child Meg was carrying. Finally, he decided to take extreme action and purchased a drug that would induce a miscarriage. Craig went as far as to put the drug in Meg's glass and proposed a toast. However, at the last second, he knocked the glass out of her hand before she could take a sip. As the days went by, Craig began acting more and more erratically. Finally, after making a scene at the Lakeview lounge, Craig revealed to Meg that her DNA test had been altered. He made it clear that he wasn't responsible but Paul was indeed the baby's father. Meg left to tell Paul and later realized that Rosanna was the one who altered the tests. At the same time, Meg remembered Craig knocking the glass out of her hand. Since that hand became infected, she realized that he tried to drug her. Craig admitted it but pointed out that he couldn't go through with it. Craig begged Meg to stay with him and let him raise her child. Repulsed by what he almost cost her, Meg ordered him out of her life and decided not to let Paul know what Craig did for fear of what he would do. Unfortunately, in the heat of anger, Rosanna let the truth slop out. As Meg feared, Paul left to confront Craig. The pair got in a vicious fight and, when she tried to break it up, Paul shoved Meg which caused Meg to fall and lose her baby.

Afterwards, Craig tried to convince Meg that he loved her but she refused to go back with him. Later, she told him he could keep Worldwide since she wanted nothing to do with it. However, a few weeks later, Meg changed her mind and returned the Company to Lucinda who unexpectedly handed it over to Paul. At the same time, Meg continued to make it perfectly clear to Craig that it was over between them. Having lost everything to Paul, Craig decided to get his final revenge on his rival by rigging his car to explode. After saying goodbye to Margo and hinting at what he was about to do, Craig departed Oakdale on a plane headed for the Cayman Islands.

Several months later, Craig returned to Oakdale at the precise moment that Katie's husband, Brad, was arrested for murder. Craig told Katie he could fix Brad's problems if Katie would be his alibi for the night Paul's car had been bombed. Katie agreed. The charges against Brad were dropped when Margo and Dani Andropoous found the "murder victim" alive and well in Chicago. His plan executed flawlessy, Craig celebrated with his accomplice—Dani. With Katie as his alibi; Margo was forced to drop the charges against Craig.

Weeks later, Craig was shocked to learn that Lucy and Johnny were hiding out in Oakdale. Though Craig tried to convince Lucy that he'd be a good father to Johnny, Lucy could not forgive Craig for his previous crimes. When Craig overheard Lucy arranging to return Johnny to Dusty, he promptly had his daughter arrested for kidnapping and sought legal custody of Johnny. In the meantime, Craig had resumed his friendship with Carly who convinced him to drop the charges against Lucy. In the end, the judge awarded Craig custody of Johnny. Undeterred, Dusty used Lucy to give him access to Johnny, which upset Craig. Though Johnny liked having both Craig and Dusty in his life, after several weeks, he stopped talking because of the confusion over his two dads. .After, Lucy lectured Dusty about the harm he was doing to Johnny's emotional health, Dusty decided to stay out of Johnny's life.

At the same time, Craig convinced Carly to go into business with him. At this point, Carly was experiencing some drama in her life—namely from Parker who ran off to get married in an attempt to seize his trust fund. When the judge allowed the underage teens to marry, Craig stepped in and offered to act as trustee of the fund so that Parker wouldn't spend it irresponsibly. Meanwhile, Craig's feelings for Carly had grown. In an attempt to provide her with some stability, Craig proposed marriage. At the same time, a healthy Rosanna returned to Oakdale! Though Craig tried to convince Rosanna that he was a changed man, she was skeptical. While staying at Carly's, Rosanna found several bottles of vodka hidden in the house. Already suspicious of Carly's behavior, Rosanna confronted Carly about her drinking problem and agreed not to say anything to Craig until after the wedding. However, on the day of the wedding, Carly had a change of heart and decided that she needed to get help for her addiction. While Carly was gone, Rosanna found themselves falling for each other. Rossana's feelings for Craig greatly troubled her, not only because of Carly but also because of Craig's actions years earlier. When Carly returned from rehab, she realized the truth and blasted both Craig and Rosanna for their betrayal. Fortunately, it didn't take Carly long to realize that she never loved Craig anyway and she forgave her sister. Though Rosanna agreed to marry Craig, when it came time to say her vows, Rosanna couldn't go through with it. After a heart-to-heart with Craig about Carly and the car accident, Rosanna gained closure, and she decided to move to Germany alone. As for Craig and Carly, they broke off their engagement and remained business partners. However, instead of the vodka business, they decided to reopen Monte Carlo.

Unfortunately, Craig didn't have the money needed to rebuild the company and liquidated Parker's trust fund to finance Monte Carlo. Later, Carly figured out that Monte Carlo didn't have an outside investor, and Craig lied that he was personally financing the venture. Suspicious, Carly hired an employee named Gabriel Carras, whom Craig had previously fired, to keep an eye on Craig. Unfortunately for Craig, Gabriel found proof that Craig had stolen from Parker's trust fund and blackmailed him. Unfortunately, the money situation at Monte Carlo only got worse with Craig's shady financial advisor leaving town. Desperate to recoup his losses, Craig set fire to the Monte Carlo offices in order to collect the insurance money with Gabriel almost getting killed when he, unbeknownst to Craig, entered the building. The day of the fire, Lily shocked Craig with the news that Gabriel was his son--the product of an affair Craig had with a maid while he was married to Sierra. The boy's mother, Lydia, asked that Craig not be told, and Sierra kept the secret telling no one but Lucinda and Lily. Bitter, an angry Craig railed at Lily and Lucinda for their duplicity.

Meanwhile, thanks to Carly, Craig was arrested for embezzling from Parker's trust fund. Unfortunately, he was also charged with assaulting Gabriel when it was learned that someone assaulted Gabriel and left him unconscious prior to the fire. When it was discovered that Parker was the one who fought with Gabriel on the day of the fire, Craig got the charges dropped. Ultimately, Carly and Craig agreed to blame the fire on faulty electrical wiring, and the insurance company paid out over $20 million dollars. Craig, however, only gave Carly $5 million, which he claimed was half the settlement. Craig talked Lily into going into the perfume business with Carly, who could never know that Craig was financing the venture. Craig ended up working with an investor who was actually working with Lucinda on a plan to financially ruin Craig by having him purchase a nonexistent factory. Luckily, Craig caught on and informed Lily of her mother's scam. Craig offered to prove himself to Lily by helping her rebound from the Carlisle scam; however, he said she'd have to put up her own money that time. Later, at Carly and Jack's wedding, Craig was disappointed to learn that Gabriel was moving back to Montega. However, he was pleased to learn from Rosanna that she was staying in town.

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