Pushed by her sister, Olivia, to produce her mystery "boyfriend", Drucilla talked Jabot executive trainee and Stanford MBA graduate, Neil Winters, into playing the part. Neil played it so well, he ended up falling in love with Olivia himself. Olivia realized what was happening, and countered by moving up her wedding date, and Nathan and Olivia married with Dru as maid of honor. Dru and Neil commiserated, and ended up falling in love. It was obvious both couples were mismatched. The scholarly Olivia was married to the former criminal Nathan, and the former criminal Dru was with the sophisticated Neil Winters. Neil supported Dru in her rise to ballerina stardom. But when she turned down a chance to tour with the ballet for a modeling career, Neil thought it unforgivable, to be giving up art for self-gratification and big money, so they broke up. Nathan and Paul exposed photographer Vinnie Russo, and Dru's "modeling career" turned out to be a porn scam. Luckily, Dru got noticed by fashion photographer Blade, and she and Blade went to work for Jabot. Jabot executive Jill Abbott fought the idea of the unsophisticated Dru as their model. At the same time Dru was doing a nude centerfold for Sensuality Magazine. Jill caught her and destroyed the film.
Shortly after Nathan Jr. "Nate" was born to Liv and Nathan, Dru and Neil reconciled and became engaged. Then Dru's centerfold hit the newsstands. The magazine had published Dru's test shots. Dru was devastated, knowing what Neil's reaction would be, so she left town.
Dru returned some time later and she and Neil were married at the Chancellor Estate.
Neil's black sheep half-brother Malcolm suddenly showed up in Genoa City, intent on patching up his differences with Neil. Neil was convinced that Malcolm was only there to freeload, but Dru got Malcolm a job at Blade's photo studio which helped convince Neil he was wrong about him. One night Dru was over-medicated for a cold, and ended up making love with Malcolm, mistaking him for Neil in her stupor. Malcolm had secretly loved Dru, but never thought she gave him a second look. His secret desires got the best of him that night when he thought she really wanted him. Dru soon found herself pregnant, and not knowing which Winters brother was the father, she considered abortion. But when the doctor told Dru she had a condition that made her lucky she had conceived, and probably never would again, she reconsidered. Dru and Malcolm decided the baby would remain Neil's no matter what, and only they and her sister Olivia would ever know the incident had happened.
After the birth of her baby Lily, Dru signed a contract and returned to modeling, which took her away from home and infuriated Neil. Neil felt that unless a wife had a meaningful job (like being a doctor like Liv), her place was in the home. In his loneliness Neil turned to the recently widowed Liv, who agreed with his Neanderthal ideas. When Dru told a reporter that she owed her career to her wonderful understanding husband, Neil relented, and they reconciled. When Dru realized that Neil was actually determined to keep Dru pregnant and unable to model, she started taking birth control pills behind his back. Meanwhile, thanks mainly to Malcolm's bond with Nate since the death of his father, Malcolm (now a successful photographer) fell in love with Olivia and proposed. Neil discovered Dru's birth control pills and moved out, determined to stay out of his wife and daughter's lives. Time passed and Dru and Neil reunited and split again and again thanks to Neil's beliefs conflicting with Dru's dreams. Dru finally took off with Lily for the runways of Paris and filed for divorce.
Neil's life was consumed with being Victor Newman's right hand man. Neil finished working on a case meant to expose Newman's underhanded HMO Lawson Medical with the attractive female attorney, Alex Perez. Alex was romantically involved with his brother Malcolm. Just about the time that Neil was ready to confess his love to Alex, she agreed to marry Malcolm. Because she had committed to Malcolm, she spent months trying to keep her feelings for Neil from Malcolm, and she avoided Neil and further temptation. Since his best friend Ryan McNeil was murdered, Neil began hitting the bottle pretty hard. In drunken frustration he admitted his love for Alex to Malcolm. Alex swore it was one-sided and hurried along her relationship with Malcolm, wanting to get married right away.
Despite the fact that the two brothers couldn't stand to be in the same room together, Neil was sent to Kenya with Alex and Malcolm to supervise a special photo shoot that Ryan had planned before his death. Malcolm overheard Alex admit to Neil that she had feelings for Neil, so Malcolm concluded that Alex had not been dishonest with him. But Malcolm didn't stay long enough to hear her proclaim she had made her choice, that she loved and would marry Malcolm. Later after slugging Neil, a stunned Malcolm took off for a location visit with their location manager, Isaac. As their vehicle was crossing a bridge, an oncoming truck created too much weight for it, and the bridge collapsed. Malcolm survived and rescued Isaac, then swam off to find their driver. Isaac saw the bridge collapse on Malcolm. They searched for weeks, the driver's body was found, but not Malcolm's, so Alex and Neil reluctantly returned to Genoa City. They finally put the pieces together, with the help of Victoria, and realized that their conversation must have led Malcolm to his death. The guilt was too much for them both. Alex returned to Minneapolis, and Neil quit his job and turned to the bottle full-time. His continual drinking led to an altercation with Victor Newman, and Neil quit his job.
Hanging out at the Olive Branch bar, scruffy, unshaven and drunk, Neil met barmaid Serena. Serena, though appearing street smart and tough, felt sorry for Neil and took him home with her where they made love. Because there had been a drunk and a child in her past, Serena related to Neil, rescued him and gave him a place to stay without judgment instead of hounding him to shape up like Olivia had. Olivia banned her son Nate from seeing his uncle. That and his estrangement from his daughter Lily sent Neil deeper into the bottle.
Dru showed up at Neil's apartment in the summer of 2002 with the now 14 year old Lily in tow, claiming Lily needed her father to change her smart-mouth attitude. But Dru was surprised to find that Neil had quit his job, become an alcoholic, and was living with barmaid Serena in a seedy part of town. After hitting bottom, Neil, with the help of Serena, decided to dry out for his daughter's sake. But he ended up getting rolled by a guy named Juice, then Juice went on to loot his old apartment finding Dru, Lily, and Olivia who fended him off smartly. Neil was convinced to check into rehab, and taking one day at a time, got a lesser job at Newman. Serena saw the writing on the wall, cleaned herself up, and kissed Neil goodbye.
Reuniting the family began to look good to Neil, so Dru and Lily moved in with Neil "for Lily's sake." At the same time Dru's psychiatrist boyfriend, Wesley Carter, who had followed her from Paris, proposed. Dru chose Neil and they became engaged. Never one to let an ex-boyfriend of Dru's go to waste, Olivia became engaged to Wes.
Dru went to work for Jabot. Newman Enterprises outbid Jabot to buy out Satine Cosmetics for Women of Color due to inside information that Dru let slip to Neil. Jabot decided to resurrect a similar shelved project of Ashley's which Dru ended up naming Tuvia to compete, and Dru became their spokes-model. Payback was had when Dru found out that Newman was trying to woo Satine creator, Damon Porter as their chemist for their newly named Safra line, and Dru stole him away to work for Jabot during Ashley's maternity leave. Jabot was still in financial trouble, but saw Tuvia as their savior, depending on their reputation and fine product to put them back in the black. But Victor could not let Jabot win the war, so he blackmailed Michael Baldwin into paying off large retailers to give them the prime shelf space normally held by Jabot. Neil tried to ignore the rumors of Victor's dirty tricks, while Dru worked hard to help make Tuvia a success at Jabot.
Now 15 years old, and still belligerent and mouthy, Lily spent most of her time on the Internet where she met Kevin Fisher in a chat room. Her friends Colleen and Sierra talked her into meeting him in person, but were aghast when he turned out to be 25 years old. Lily fell head over heals for the manipulating Kevin, but her friends were convinced he was bad news and even interrupted what was to be Lily's first sexual encounter at Kevin's apartment. Lily broke off their friendship. Kevin later talked Lily into sex to "prove their love," but her girlfriends told Neil and Dru about it to help save Lily. Neil stormed over to Kevin's apartment, and Lily escaped out a window and down the fire escape as Kevin let him in. Neil threatened the cowering Kevin that if he found out he was messing with his daughter he would be charged with statutory rape, and Neil would kill him if he touched her again. Kevin took revenge on Colleen by trapping her in the walk-in cooler at Gina's Restaurant and setting the restaurant on fire. Colleen survived, and Lily finally realized how dangerous Kevin was. Lily had to confess all to her parents, and though luckily not pregnant or HIV-positive, she was diagnosed with Chlamydia. At least it brought her close to her parents again and she lost her attitude. Kevin was never charged with statutory rape because the police advised there was not enough evidence since his VD had been cured prior to testing.
Dru and Neil were remarried in a lavish Japanese wedding on Ryukyu Islands, Japan, with Lily as maid of honor, Olivia as bridesmaid, and Jack Abbott as best man.
After Victor Newman was found guilty of corporate bribery, he temporarily stepped down as CEO of Newman Enterprises, and Neil was chosen Acting CEO. After using an untested synthetic hair straightener being developed by Jabot, Dru's hair fell out in clumps. Not long afterward, Dru quit her job at Jabot and went to work at Newman Enterprises for her husband Neil.
Lily met troubled teen Devon, who was belligerent and just hung around watching and resenting the rich kids helping the neighborhood kids fix up the new Market Street Recreation Center. Lily's attempts to befriend him were rebuffed at every turn as Devon did not trust anyone; especially an obviously rich kid. To get her off his back, he made up answers to her questions, telling her how he went to a school in the rich part of town and was part of a big happy family. Later when Lily realized he was lying, Devon told her how he'd been shuttled from one group home to another since he was taken from his crack-head mother, and that his father was dead. Devon was living in a foster home, but was about to be kicked out for his behavior. Just as the bubbly and sweet Lily was finally getting through to Devon, and he started helping out and treating everyone better, he was told by his social worker, Lorena Davis, that there was no group home available so he'd have to be sent to a Level 12 facility which sounded more like jail.
Drucilla got to know the boy and saw herself at that age. Remembering how she had gone down the wrong road until Nathan had rescued her and taught her to read, she wanted to give back by helping Devon in the same way. So Dru convinced Neil and Ms. Davis to allow them to be temporary foster parents. Devon blossomed once he knew someone cared, and he and Lily became very close. During this time, Devon told Lily he'd seen his father only once hanging out in front of a convenience store.
Devon became part of the family, learning table manners, reading books, and such. Neil was hesitant, but Dru plotted to make the arrangement permanent, and lied to Ms. Davis that Neil was on-board with permanent fostering of Devon. When it was discovered that Neil knew nothing about it, Devon was to be sent to a Level 12 facility, but he ran away with Lily instead. Devon was found and Victor Newman, whose probation officer was also Ms. Davis, volunteered to take him until a group home could be found. Victor and Devon bunked together at the Rec. Center in sleeping bags for a few weeks. The day Devon was to leave, Neil finally gave in and agreed to permanent foster care.
Three years after he had been declared dead, Malcolm showed up in Genoa City, very much alive, sporting cornrows and a bad attitude. Malcolm was out for revenge against the brother who he thought had stolen his fiancé and left him for dead in Kenya. Malcolm explained that a family had taken him in and nursed him back to health, then he ended up having to take care of them. But Malcolm had returned mostly to see his step son Nate again. Olivia was resentful that Malcolm hadn't made himself known to Nate as soon as possible, sparing him the devastation of his death, so made Malcolm wait until Nate returned from boarding school at the end of semester to reveal himself. (But both Malcolm and Liv left town before that ever occurred.) Until then, Malcolm took a job as a waiter, and later was named Manager at Crimson Lights, and Olivia convinced him to stay in her extra bedroom. Malcolm hadn't forgotten the possibility that Lily might be his daughter, so Dru had a paternity test done. Although Lily had known that Dru and her uncle Malcolm had once been an item and wondered, when it turned out that Malcolm really was Lily's father, they decided not to tell the truth to Malcolm, Lily, or Neil.
Devon's birthday came around, but no one remembered it. Disappointed, but unwilling to tell anyone but his friend Sierra, he skipped school and headed for the zoo. Later that night when he was discovered missing, Sierra tipped them to check the zoo. Dru, Neil, Lily and Malcolm found a terrified Devon marooned in the lion habitat, eye to eye with a lion. Malcolm climbed down into the pit and used skills apparently learned in Africa to distract the lion while Devon climbed out with the help of Neil, then was followed by Malcolm. Lily and Devon brought around the SUV to pick them up, but she lost control when it skidded on the ice and it struck Neil. Neil made up with Malcolm, asking him to take care of his family in case he didn't make it through surgery, then Neil relieved guilt for the accident from Devon and Lily, and said goodbye to Dru. In the waiting room, Lily blamed Devon, so when Ms. Davis arrived, he asked be put into a group home. Dru intervened and assured Devon that families were all about love and forgiveness. Neil needed blood, and Lily wanted to donate, but Malcolm insisted he be the one. Devon helped Lily see that Malcolm needed to give back to his brother to mend the relationship, but Malcolm was really more interested in the possibility that Neil was not Lily's father. Neil survived the surgery just fine.
Neil was disappointed when Victor named his son Nick CEO of Newman, and Neil became Chief Operating Officer and Right Hand to the CEO. When Nick let the power go to his head, cancelled Neil's pet projects and refused Neil's advice, Neil quit his job at Newman. But when Nick felt threatened by the possible return of his sister Victoria, he gave Dru Victoria’s position of Director of the Cosmetics Division with the stipulation that Neil would return and would mentor Dru in the job. Dru came up with a new project called "Seasons" which featured fragrances for each season of the year.
Devon found his mother, Yolanda, homeless and camping in the park. He tried to talk her into going into a free state rehab facility. Yolanda refused and claimed she was off the drugs. So Devon took her home to the Winters' apartment, let her clean up, and she stole Neil's expensive watch before she left. Yolanda used the watch to buy enough drugs to overdose, and Devon found her unconscious in the park. Yolanda recovered and went into rehab. After rehab, she went to live with the Winters family, got a nice job in the Jabot mailroom, but then blew it all by coming on to Neil. Neil shot her down, while Devon walked in on them. He turned down Yolanda’s offer to leave town with her, and she packed and left for her sister's in Seattle.
One day Lily overheard an argument between Phyllis and Dru and discovered the long kept secret of her paternity. She was very upset and emailed Daniel about it, but accidentally sent it to "Dad" instead of "Daniel". She discovered her error and tried to intercept the email, but in the end Lily ended up telling Neil the truth; that she was not his biological daughter, and that his brother Malcolm was her father. Neil blew up at Dru and never let her completely tell the story of how it had happened. Neil and Dru separated, and Dru began living with the also-separated Sharon Newman at the Newman Ranch. Neil began seeing co-worker Carmen Mesta who encouraged Neil's dream to own a jazz club. Carmen found him a space which he bought, renovated, and named Indigo. Devon began working part time as an intern at Newman Enterprises and attending GCU.
Dru began following Carmen and Neil on their "business meetings" and observed them hugging and kissing. She was so enraged she threatened Carmen and fought with Neil. When the time came for the NVP Retreats grand opening party, Dru showed up on the arm of a businessman named Edward and made a drunken scene from which Neil carried her out of the room. Dru ended up tricking the maid into letting her into Carmen's room and was discovered by Carmen and Neil cutting up Carmen's clothes. Carmen called the police and Dru went to jail. Dru was sentenced to 2 years probation, 60 hours of community service. 60 hours of counseling, no communication via phone, written, e-mail, nor could be within 500 feet of Carmen unless it was business related and a 3rd party present. Dru continually violated the restraining order by confronting Carmen, so Dru was fired from Newman, but was later reinstated.
In the middle of the Winter's marital problems, Devon went deaf after surviving meningitis. They reconciled, and the family bound together to support Devon by learning sign language and having their home equipped for the deaf. Devon was coping well even though he was a music major, but he began looking into having a cochlear implant. Devon felt he was being smothered by his over-protective foster parents, so he moved out to live with Lily and her boyfriend Daniel in a rented house near the GCU campus.
Neil gave Dru the job of decorating his jazz club Indigo and was hoping Devon would work there too. Indigo's successful grand opening featured Aaron Neville with a sign language interpreter just for Devon. But afterward, Carmen turned up bludgeoned to death in the alley behind the club. Dru, Neil, Devon and Lily all appeared before the Grand Jury to testify, and were among the murder suspects. But in a surprise turn of events, Devon was arrested for the murder of Carmen. While Devon was out on bail awaiting trial, his cochlear implant surgery was successful, and he was able to hear again. Neil and Dru took the opportunity to legally adopt Devon once they heard that his mother was back on drugs. After Jana Hawkes confessed to being was the real killer, Jana disappeared and both Dru and Devon were exonerated.
In April of 2007, Sharon and Phyllis began fighting on the edge of a cliff during a NVP photo shoot, and Dru intervened. They lost their balance and fell backward. Dru sailed off the cliff into the river below, and Sharon was left hanging onto the edge for her life. Phyllis tried to save her, but she lost her grip and Sharon also fell to the river below. Rescuers combed the area and found Sharon's lifeless body, but she was revived and lived. Dru was never found. Only the jacket she wore was found below the falls, so she was presumed dead. A prayer vigil was held at Indigo, where memories were shared by family and friends. But Neil believed that Dru was still alive, and declared that he would not give up looking for her. For a while Neil was turning back to the bottle in his despair over losing Dru, but he stopped for the sake of his children.
After Nick was presumed killed in a plane crash, Victor made Neil Co-CEO with Victoria at Newman Enterprises. New Co-CEO, Neil, gave his son Devon a big project of his own to oversee with Kline Outdoor signs, though Brad was not confident in his ability to handle it. But Devon not only got kudos from Kline, but also was given a high profile account of Brad's, and was becoming a serious up & coming businessman. Although after Nick was found alive and he resumed the Co-CEO position, Nick and his father had a huge falling out and he was fired, so Neil was again made Co-CEO with Victoria.
Lily became interested in 31 year old Cane Ashby. He returned her feelings, though he tried to deny it, due to her being only 19 and Neil's disapproval, so they agreed to remain just friends. Meanwhile on election day, Neil met Karen Taylor, Nikki's campaign manager, and helped her when she locked her keys in her car, and they began dating. After the campaign was over and Jack won the Senate seat, Neil asked Karen to take his deceased wife Dru's job at Newman Enterprises. They clashed when Karen changed Dru's marketing plan and Victor supported her. Neil apologized, realizing he was overly sensitive to anything that concerned Dru including when Karen turned up with one of Dru's hats they had donated, liking the same movies that Dru had, etc. When Newman got involved in the Clear Springs Development Project, Karen was in charge of public relations.
Devon and Lily had a hard time getting past Neil’s "disrespect for Dru" but came to accept Karen when they celebrated Thanksgiving together and realized she was a great person with family traditions too, like her chicken adobo. By Christmas, they happily invited her themselves. Neil caught Karen singing at the piano at Indigo, told her how good she was, and encouraged her to sing at the club. Karen had terrible stage fright, but Neil lovingly got Pat Benatar to help her overcome it. Pat taught Karen a trick, then Karen sang fearlessly at the club. After her debut, Neil told Karen that he loved her and asked her to marry him. She said she didn’t think they were ready, but agreed to move in with him, and realized she had been right when she found herself surrounded with Neil's memories and all of Dru's things.
Lily won the Fresh Face of Jabot contest which Cane was in charge of, and began learning to model. But hard as they tried to remain just friends, Lily and Cane ended up consummating their relationship on Valentine's Day. Caught by Neil leaving their room at the Athletic Club, still bathed in afterglow, Cane set the record straight as he told Neil that he was in love with Lily and promised not to hurt her. Lily got involved with her modeling career and flunked out of college, then discovered that she was pregnant by Cane. After much indecision, Lily told Cane and her father that she was pregnant. Lily went to her mother's old ballet studio to feel close to her mother, and decided to have the baby. Later Cane staged a lovely marriage proposal at the same studio, but Lily was hesitant to say yes, afraid he wanted to marry her for all the wrong reasons.
Meanwhile Neil was making plans to raise Lily's baby with Karen, without consulting Lily, Cane, nor Karen beforehand; causing Karen to feel disrespected and move out. Karen quit her job at Newman and prepared to move to New York to work for a romance novel publisher. But when Cane & Lily went for the first ultrasound, it was discovered that there was no more baby. It had dissolved on its own due to imperfection. Cane and Lily were devastated, and Karen was great consoling Lily. After a bit of soul-searching, Lily decided to go back to college and model only as a part time job.
After a time Neil regretted his treatment of Karen, called her, then showed up at her apartment in New York. He asked her to return and to marry him, but she turned him down, and Neil returned to Genoa City alone. Though not long afterward, Karen showed up in Genoa City. Karen had to beg Adam, who was now in charge at Newman, to get her job back, then Karen and Neil resumed dating.
Karen became good friends with both Lily and Victoria through their troubled pregnancies and admitted that she would have loved to have about 5 kids, but couldn't. Karen had lost her mother to ovarian cancer when she was 12, was taken from her family to live with an aunt and uncle in another town, then took care of her ailing father, and went through a long relationship that went nowhere, so never did have children. Later she had a hysterectomy to prevent inheriting the same cancer, and because she knew how much Neil loved kids, she wasn't sure how to tell him.
During a surprise 21st birthday party for Lily, Devon's Aunt Tyra and the precocious and talented 12 year old Ana arrived from Seattle. Cane realized that they didn't have money for a hotel, so he paid for one. But Neil was highly suspicious of their motives for coming to town, especially after they found out Tyra had lost her job as manager the Pembroke Inn in Seattle, and had been evicted. But Tyra was honest about her circumstances and Neil wanted his son Devonto get to know his real family, so soft-hearted Neil invited them to live with him and Karen until they got back on their feet. As weeks went on, Karen was not pleased with the arrangement, and asked Tyra to look for her own place, but Neil nixed the idea. Ana had a beautiful singing voice, but was afraid to sing in public. Thanks to Karen relating her mutual stage fright, Ana began singing for the family at Indigo and then with Devon at the annual charity gala which prompted Kay Chancellor to offer her the annual scholarship for gifted students to a Music School in New Hampshire. Tyra was reluctant to accept because Ana was not really her daughter, but the daughter of her crack-head sister Yolanda, so she was afraid her deception all these years would be exposed. Neil was supportive, and Kay paved the way for Ana to get into the school regardless. Even Devon was unaware that he had a sister. Tyra explained that when Devon was a child living with his grandmother, Yolanda came home pregnant from one of her many disappearances and Tyra, who was only 15 and living with her father (Devon's grandfather), raised Yolanda's baby who was Ana. Devon and Ana got along wonderfully as they were both interested in music, writing and singing together.
When Victor was declared dead when the fishing boat he was on was caught in a storm in Mexico, the will was read leaving his youngest son Adam in charge of Newman. Adam fired Neil and hired Brad as CEO of Newman, naming himself as Chairman of the Board. But Victor was discovered to be alive and Adam was fired. J.T. had the pleasure of ushering Adam out of Newman Towers. To avoid paying Brad's hefty severance package, Neil and J.T. talked Brad into voluntarily resigning, or else the fact that he took company secrets from Newman to Jabot would be exposed.
When Neil was unfairly fired from Newman Enterprises by Adam, Devon quit as well in solidarity. But when Neil was later made CEO of Newman again by Victor, Devon declined to return because he had decided to concentrate on his music.
A few months after Ana and Tyra had left, Katherine got word that Ana had left her school. Neil and Devon tried to contact them and found that Tyra had given up their apartment. They both arrived in Genoa City again by train on the way back to Seattle. Tyra told Neil that things just didn't work out in New Hampshire, the rent was too high and the pay too low. Neil pointed out that she had nothing to return to in Seattle. When Devon offered to share his house with them so they didn't have to impose on Neil and Karen, Tyra agreed to stay and take back the manager job at Indigo.
In October 2008, Lily went to visit her Aunt Olivia in New York City while she was lecturing there for Doctors Without Borders, and returned to Genoa City with her. Olivia was surprised to learn that Neil's current flame Karen was a former patient of hers in New York City. Neil asked Karen to marry him but before she would accept, Karen explained about her inability to have children. Neil said he understood, and they became engaged. Much as Olivia liked Karen, after meeting Tyra and seeing how much chemistry she and Neil had, she advised Neil that he was marrying the wrong woman. Tyra may have gotten over her attraction to Neil when she started dating Detective Gil Wallace. But Gil spotted Ana on a missing person's bulletin put out by Yolanda, and had to confront them to take Ana to a foster home until her custody could be straightened out. Billy Abbott got his young attorney friend, Rafe Torres, to take the case, but Yolanda further complicated things by disappearing. Meanwhile Neil renewed his foster care license and he and Karen decided to marry earlier than planned to help them get custody of Ana. Their wedding was held on New Year's Eve 2008 at Indigo with Victoria as Matron of Honor and Victor arriving at the last minute to be Neil's Best Man, while Olivia was disappointed that Tyra did not interrupt the wedding and declare her love for Neil. Neil and Karen went to court the next day and got custody of Ana, but with the restriction that Tyra could only see her during supervised visits. Ana was thrilled to be back with family, but Tyra was crushed.
Karen became so attached to Ana that she wanted to legally adopt her, much to Tyra's opposition. Rafe got the courts to terminate Yolanda's legal rights to Ana, and Tyra celebrated by telling Neil how much she cared for him and kissed him, which Karen secretly witnessed. In retaliation, the next day Karen told Tyra that their adoption of Ana was in the works with Neil's blessing, so Tyra took Ana and attempted to flee Genoa City. Neil found them, thanks to Ana's tipping him by cell phone. When the police arrived, Neil told them that they were there with his permission. When Neil confronted Karen about provoking Tyra to run away, she confronted him about his kiss with Tyra. Karen told him it was time for him to get his priorities straight if he still wanted her in his life, and that meant firing Tyra. Neil agreed, but his telling Tyra ended up in a sexual encounter in the middle of the empty Indigo. Devon walked in and saw them and later confronted Neil, asking why he was risking his marriage and family. Neil later admitted his sexual encounter with Tyra to Karen who forgave him, afraid that it would hurt their adoption of Ana. But in court Neil convinced the judge to give sole custody of Ana to Tyra because she deserved her after raising Ana so well all these years. Karen was so devastated that she accused Neil of using her to get over Dru, and left him, leaving her wedding ring behind. A week or so later, Tyra ran into Neil at Kay Chancellor's wedding, and they admitted their attraction, but decided to wait to act on it. Karen showed up again at Indigo during the pre-wedding party for Lily and Cane with divorce papers for Neil to sign, and caught him dancing with Tyra. He reluctantly signed.
Neil finally realized that not being a Newman he would never get any further, so he quit his job as CEO of Newman Enterprises, and was hired by Katherine as CEO of Chancellor Industries.
Devon found out that Tyra was not really related to him when his Aunt Virginia told him how his grandmother had taken her in when her parents died. Devon confronted Tyra, and Tyra explained to Neil who walked in on them arguing. Devon left, and said that he was through with the both of them and their lies.
Cane and Lily married, but after Cane was proven to be a fraud and not the real Phillip Chancellor III, Neil made Lily come live with him and smothered her with fatherly protection from him. Cane sold the bar to Mackenzie and decided to leave town. Thinking that she was pregnant and Cane needed to know, Lily asked him to stop by and see her. Hearing Cane say how sorry he was that he messed up her life, that he was leaving town, and that luckily she was not pregnant, Lily decided not to tell him. Olivia diagnosed Lily as not pregnant, but instead she had a mass on her ovary which was cancerous. Lily asked for Cane, Devon and Liv thought it would help, but Neil forbade it. Mackenzie tracked down Cane, persuaded him not to leave town. Lily slipped out of the hospital convinced that harvesting her eggs for future children was more important than her scheduled surgery, but Cane was able to convince Lily to return. After surgery, Olivia delivered the news that they had had to do a hysterectomy, but that luckily some eggs were saved. It wasn't long before Lily and Cane reconciled and she moved back in with him. As they fought her cancer together, Neil came to realize how much Cane loved his daughter and grew to accept him.
Devon was having sexual fantasies about Tyra yet whenever they were around each other he would attack her for breaking up Karen and Neil. In the middle of an argument, Devon and Tyra fell into each other's arms and had sex on the couch at their place. Devon’s girlfriend, Roxanne, walked in on them, and later returned with Devon's things from her place and broke it off. Devon, feeling guilty, admitted to his father what happened between him and Tyra. Neil was livid when Tyra later arrived to apologize, and she left promising that Ana would still visit her family.
In December 2009, Malcolm showed up out of the blue in Lily's hospital room as she was fighting another infection caused by her cancer treatments. He explained that he had been on photo shoots in foreign lands, but had received her letter telling him she had married Cane, was aware and heartbroken over Dru's death, and had met Olivia at Heathrow Airport and found out about Lily's cancer. Neil took him to task outside Lily's room for his not keeping in touch, especially with Lily. But they since decided to bury the past for Lily's sake, and Malcolm accepted the photographer position with Restless Style and intended to stay in Genoa City. Lily’s Aunt Olivia finally arrived from Haiti where she was working with Doctors Without Borders and began helping Lily decide on her options to fight the cancer. Shocked to see Malcolm the first time in years, it was realized that Malcolm had not met Liv at Heathrow like he claimed. Neil and Malcolm became at odds again as Neil pressured him for more information, and each tried to be a doting father to Lily. Devon finally graduated with a degree in Music and was offered a good job in business. Neil was upset when he turned it down to work for Malcolm as his photography assistant for an income to support his music career. Neil felt that Devon should pursue a real career more befitting a college graduate.
Lily’s friend Mackenzie agreed to be a surrogate using the eggs that were harvested during Lily’s hysterectomy, which turned out to be twins, a boy and girl. Olivia approached Lily with an experimental procedure using stem cells from the babies’ placentas that could save her life, but both Lily and Mac turned it down fearing it may harm the babies. But when Mac went into early labor, the twins Charlie and Matilda (Matty), were born two months prematurely, and their amniotic fluid was saved for Lily’s treatment which saved her life.
Neil and Ashley Abbott began dating and became lovers. But Ashley and Tucker McCall got closer and ended up making love. Afterward, Ashley felt guilty, and once back in Genoa City, considered admitting it to Neil. But before she could, Neil suddenly sold Indigo to Jeff and Gloria, and told Ashley he felt he should spend more time with his family, and they should just remain friends.
In July 2010, Sofia Dupre arrived in Genoa City from Europe and revealed that she was Tucker McCall’s “right hand.” Neil took an instant dislike to her, only to find out that she was his brother Malcolm’s mystery fiancé. Sofia did her best to be part of the Winters family, always there at special occasions, and willing to help out when needed. Even Neil finally came around to respecting her and even liking her personally.
Just before the twin’s Christening, Immigration demanded that Cane appear for deportation because Lily had gotten well. Deportation loomed closer for Cane, but Sofia saved the day by convincing Tucker to approve Cane as liaison with their corporate partner located where Cane grew up in Canberra, Australia. Because Cane was uniquely qualified, he was granted an eight month work visa, and Cane, Lily, Neil, and Michael arrived in time for the Christening. Later at the reception, Phillip returned from Australia and warned Cane that he was still in danger there, and he dared not go back.
Needing money to pay off Blake Joseph, one of the cattle rustlers who had been after Cane in Australia, Cane checked the Internet for how to take on a new identity. Cane located the name of a dead person named James Collier and ordered a copy of his birth certificate. Cane presented Sofia with a resume for James Collier and convinced her to hire him sight unseen, intending to do Collier’s work himself, and using Collier’s paycheck to pay the blackmail. Tucker became suspicious of Collier, and requested Cane deliver some files to Collier to present a report on them, along with a face-to-face meeting with Tucker, due the following day. Cane stayed up all night working on the report. As Cane was making excuses for Collier’s absence to Tucker, Blake showed up claiming to be Collier. To make things easier, Blake told Tucker that he went by the name Blake rather than James. After they both had left, Tucker confided in Neil that he still did not trust Collier, and woe to Cane if Collier was not what he claimed to be.
The time came when Blake was assigned a project that Cane was not expert enough to handle, and Sofia and Neil were ready to fire Blake. But Sofia got Cane to admit that Blake was a fraud, and after hearing the story behind it, she agreed to help him get the blackmailers paid off to protect his family from harm. Colin put more pressure on Cane by asking Jill to marry him, and she accepted. Tucker discovered that Blake was a fraud. He called in Sofia, and when she tried to explain, he fired her and Cane. Sofia confessed her part in the hoax to Malcolm, then Neil, saying that she only wanted to help Cane who was a good man in a rough place. Both men were mad at Sofia, and left her behind while they went to help Lily pick up the pieces.
Sofia got Tucker to listen to her explanation of why she helped Cane. She reminded Tucker how he saved her father’s job as an economics professor, and that she felt she had been “paying it forward” by helping Cane. Tucker told Sofia that he expected her to cooperate with the police or face embezzlement charges with the rest of them. The mob boss, Colin, ordered Blake to go home to Brisbane, but asked him for one last favor before he left; to keep Cane from interrupting his wedding to Jill. Before Blake left for the church, he got a text message from someone called “Rippley” tipping him that Colin was not to be trusted and was setting him up if he returned to Australia.
Cane went home to tell Lily the truth about him and that Colin was his father, but she was at the church waiting for him, ready to forgive him. So Cane wrote a note for Lily and made a video for the kids, just in case he never saw them again. As Jill and Colin said their vows, Cane walked up the steps of the church, followed by Blake. Lily walked out the front door and saw them fighting. Blake turned the gun on Lily to stop Cane, but Cane jumped Blake to protect his family. The gun went off shooting Cane in the chest, and Blake fell down the steps, breaking his neck and died as he landed. Lily slipped on the ice, and the twin’s carriage went careening down the steps, but Neil arrived in time to catch it and save the twins. Cane lay on the steps bleeding as Jill and Colin walked out of the church married. Lily and Jill cradled Cane’s body and begged him to hold on as Neil called 9-1-1. Colin looked dazed as he watched his son dying. Lily told Cane she forgave him and loved him, and Cane breathed his last breath telling Lily that he loved her. The paramedics arrived, but they could not revive Cane.
Malcolm and Sofia arrived and took the babies home, and when they walked into the house, a gust of wind blew Cane’s note behind the counter. Neil took a sobbing Lily into the church to talk. Jill and Colin went home to the Chancellor estate covered in blood, and told Kay, Murphy, and Billy that Cane was dead. Billy went to console Lily, and promised her that he would write an article on Cane’s heroism. While Kay and Jill hugged and commiserated their loss, Colin went to the morgue to identify the body. He apologized to his son, saying that because of him, both his son and his daughter had been gunned down in the street. Colin promised Cane that his children would be spared from his destructive life. Lily arrived at the morgue with Neil to say her final goodbye to Cane.
Malcolm told Sofia that you don't lie to people you love and leave them out of important decisions, reminding her of the lies about Lily's paternity which caused him not to trust anyone. Then Malcolm and Sofia canceled their wedding. Sofia apologized to Neil for causing Cane's death, saying that Cane might still be alive if she had gone to Neil with what she had known. Neil told Sofia that she was not responsible, that what she did had been out of compassion for Cane and their family, and with the type of people who were after Cane, he could have died anyway, and Neil hugged her.
Tucker admitted to Malcolm how much he missed Sofia and that the bio-fuel project would probably end up being scrapped without her. Tucker and Malcolm agreed that maybe they had been a little rough on her. Yet when Neil repeated it to Malcolm, Malcolm replied that Sofia deserved to be fired. Neil and Sofia commiserated and ended up having sex on Neil's sofa. Malcolm showed up afterward, ready to forgive Sofia for lying to him. Neil went to Tucker and persuaded him to rehire Sofia. Meanwhile Malcolm and Sofia made up, and the engagement was back on.
Because Adam had made a deal with Victor to claim that Adam had forged his children's trust agreements to avoid losing their breach of trust lawsuit, Neil felt obligated to tell the truth. Neil testified at the arbitration hearing that when Adam was in charge at Newman, Neil had kept Adam from accessing anything that would have made the forgery possible. The judge awarded Abby, Victoria, and Nick five hundred million dollars each, and ordered Adam arrested for perjury. Victor left with Michael, demanding that he find a way to overrule the judge's decision. The Newman children left to celebrate, but found it difficult when they realized and felt guilty that the verdict had come down on their father's birthday. Neil also felt guilty for turning on his former boss and friend, Victor. Afterward he ended up picking up Attorney Leslie and taking her home for sex, but aborted it because he kept thinking about Sofia instead.
Malcolm and Sofia were married in the same church where Cane was murdered, which was rough on Lily, Jill and Colin. Lily was matron of honor, Neil best man, and Tucker gave Sofia away. In attendance were Nate with his mother Olivia, Devon with Roxie, Ashley was there with Tucker, Leslie with Neil, Jill with Colin, and Daniel with Lily.
While on their honeymoon, Malcolm found a pregnancy test kit in Sofia's bag. He pushed her to take the test, the results were positive, and Malcolm phoned Neil to tell him the big news. Neil couldn't help but wonder if Sofia was pregnant by him, rather than by his brother. Seeing them together, hands touching and in deep discussion, Olivia guessed that Neil could be the father. Olivia confronted Sofia, who told her that as far as she was concerned the baby was Malcolm's. So they plotted to tell Neil an earlier due date to convince him that he could not be the father. Sofia was discovered to be Rh-negative after a pregnancy incident put her in the hospital. Because Neil was Rh-positive and Malcolm Rh-negative, there was a fifty-percent risk for her baby. So Sofia told Malcolm the truth -- that the baby might be Neil's. Malcolm moved to a room at the athletic club. Sofia spoke to her doctor, Olivia, about methods of finding out the paternity of her baby without risk to its life. Testing for Rh-factor symptoms showed none, so with the paternity still in question, they decided to wait until after the baby was born to test. But a sonogram showed that the baby would be a boy.
At the family birthday party for Lily, she noticed that Malcolm and Sofia appeared not be getting along. Sofia admitted that they were separated, and Neil confirmed that he might be the father of her baby. Lily, Daniel, and Devon were shocked considering how Lily herself was conceived.
Several months following the death of Cane, it was revealed that the hit was planned by Colin, but Cane's evil twin had taken his place that day, and it was Celeb who was killed. Cane posed as Caleb during this time and attempted to find justice for his brother and sister Samantha with his mother Genevieve. Neil was instrumental in finding the note that Cane had left for Lily the night of his "death" which admitted that Colin was his father and that he had a twin named Caleb. When Cane revealed to Lily that he was alive, she felt betrayed and refused to forgive Cane.
Sofia went into labor and Malcolm took her to the hospital where she delivered a baby boy whom she named Moses, after Sofia's father. The long-awaited paternity test revealed that Neil finally had a son of his own. Later Malcolm presented Sofia with divorce papers, which she regretfully signed. Malcolm said goodbye to only Phyllis, and boarded a plane for Guam. Neil brought Sophia and their son, Moses, home to live with him the next morning.
Moses Dupre Winters was christened with Tucker and Olivia as godparents. Afterward, Neil asked Sofia to marry him. She thought it was a bad idea since she knew it was for convenience, not love, but later after discussing it with Olivia, Sofia changed her mind since she loved Neil. Devon, Lily, and Cane with the twins spent Thanksgiving at Neil's, where he and Sofia announced their engagement.
A week before Christmas, Reverend Fulton called to say goodbye to Sofia and Neil because he was leaving their parish, which caused an impromptu wedding. Neil insisted that Devon attend his conflicting meeting with a big record executive. As Cane and Lily stood up for Neil and Sofia, they both wistfully reflected back to their own wedding. Afterward Neil strangely disappeared without a word, and showed up at Devon's studio, leaving Sofia alone to welcome Devon and Tucker who arrived late.
Katherine asked Neil to return as CEO of Chancellor, and he began to consider it. Then Genevieve Atkinson asked Neil to become the COO of her newly-acquired company, Beauty of Nature, but Neil later turned her down.
After Devon confided in Harmony that he was having some trouble hearing the finer parts of the tracks in editing Angelina's song, Harmony suggested to Tucker that he look further into some Cochlear implant research that his company was already funding to help Devon. Devon initially refused help from Tucker when he found out, but Harmony and Neil talked him into giving Tucker a chance to help his son. Devon was scheduled for surgery, and Tucker let Devon use his private jet to go to Dallas. Devon asked Neil and Harmony to accompany him.
Cane and Lily decided to remarry in a small family wedding. Malcolm sent flowers, and Devon and Neil gave their blessings. Traci gave Lily Colleen's bracelet, and Olivia gave her Dru's comb which Lily had worn in her hair at their first wedding. But the day before, Katherine surprised them by moving the wedding to a friend's villa in Provence, France, and flying friends and family there in her private jet. Katherine stayed home for Delia's birthday party. The wedding was held on the beautiful grounds of the villa with Abby as maid of honor, Devon as best man, and Neil giving away the bride. The vows were spoken informally about second chances, and they exchanged both their old and new rings. Afterward, a reception was held in the garden.
The evening before Devon's surgery, while at a restaurant in Dallas, Tucker toasted Devon saying he had "such great respect the man who happens to be my son." But seeing how wound up Harmony was, and how she and Neil were enjoying each other, Tucker warned her not to get involved with Neil, and that he was looking out for Sofia, his oldest friend. Harmony claimed that she was not high nor after Neil. Devon had a transducer successfully implanted in each middle ear, but came out of surgery temporarily deaf, as expected. Devon went home to heal for a few weeks before the devices were to be turned on.
Katherine begged Neil to forgive her and return as CEO of Chancellor. Neil agreed, saying that he realized after what Katherine had done for Anna and for Harmony that she wasn't selfish like he had thought.
When the implant devices were finally turned on, the whole family was there to rejoice when Devon could hear clearly again. His first request was to hear Angelina's new song, and he was amazed that thanks to Tucker it sounded the way he had heard it in his head.
Tucker and Sofia staged a fight in Victoria's presence, and Sofia was fired. Sofia then asked Victoria for a job with Beauty of Nature but was turned down. When Neil offered Sofia a job at Chancellor, she admitted that it was all part of a plot to get inside information to help Tucker buy Beauty of Nature from Genevieve. Sofia still worked for Tucker, and deception and underhandedness had always been part of her job. Neil became disenchanted with Sofia's integrity, and spent the evening with Lily, Cane, and Harmony. Their fooling around together at Devon's recording studio and cheering him up caused Neil and Harmony to get even closer when they slow-danced and kissed. Neil and Harmony admitted that they were drawn to each other, but would try to avoid each other for everyone's sake. But later Neil admitted to Sofia that he had feelings for Harmony, and Sofia was heartbroken. After Harmony and Tucker were caught in bed together by his wife Ashley, Sofia told Harmony she hadn't changed a bit, and to stay away from Neil. It wasn't long before Sofia realized that Neil would never love her, so she filed for divorce. Neil tried to get her to buy a condo apartment in his building that was up for sale, but she moved to an apartment somewhere else in Genoa City instead.
The theme of the 2012 annual Chancellor 4th of July pool party/barbeque turned out to be forgiveness. While Murphy tended the grill, Devon forgave Katherine and Tucker, with Roxanne and Ana beaming their approval. Ashley had forgiven Tucker so they attended together, and Sofia told Neil that if he wanted Harmony he needed to pursue her. Harmony tried to reconcile with Ashley, but she refused to forgive her. Devon gave Harmony and Neil his blessing if they wanted to be together. Devon gave Harmony and Neil his blessing if they wanted to be together, and they began dating.
Sofia was offered her dream job in New York City, but after Neil warned her that she would not be taking their son or face a custody battle, she declined.
Harmony suddenly tracked down Neil to tell him that although she loved Katherine, that she and Devon were in a good place again and she cared a lot about Neil, she was leaving town. Harmony explained that Ana was having trouble in school and needed her mother "out east", kissed him goodbye, and left.
After gaining Adam's share support and teaming up with Tucker, Jack took the opportunity for a hostile takeover of Newman Enterprises. He offered Neil the job of CEO of Jabot. After discussing it with Katherine, and realizing that Katherine actually wanted to come out of retirement and run Chancellor again, Neil accepted. After accepting, Neil made Lily head of the Jabot marketing team, made Cane his right hand man, and hired Devon as a marketing intern. He then asked Leslie to become Jabot's chief legal advisor. She initially turned down the position due to their prior romantic relationship, but after assuring each other that it would be strictly business, Leslie accepted the position. Devon and Lily began promoting their romantic relationship again to help loosen Neil up.
Leslie's younger brother, Tyler, a successful graphic designer who wanted a job at Jabot, made a pitch to Neil and Jack, including graffiti on walls of only a single eye, then eventually announcing a new eye shadow line. Hoping to show that Jabot is not just for boring old ladies, Tyler intended it to bring in new demographic. Jack said no, and Neil, feeling micro-managed, quit. But both changed their minds, and Tyler was hired to work for Cane in marketing. But Cane became jealous because Tyler kept flirting with Lily.
Concerned that Jack was addicted to pain killers, and he would lose the only parent he had left, Kyle got Phyllis, Billy, and former alcoholic Neil to help stage an intervention. But Jack claimed they had insulted him, fired them all, and threw them out of his house. Jack made Cane acting CEO of Jabot. His first task was to fire Tyler, but Lily later convinced Cane to give Tyler another chance. Leslie guessed and admired Neil for overcoming his alcoholic past, and now that they were no longer working for the same company, fulfilled their sexual desire for each other. Lily and Cane were pleasantly surprised to find Neil and Leslie together in his apartment the next morning. Cane let Neil know that as CEO of Jabot, he was putting Neil in charge without the title for the sake of Jabot. Once Neil and Leslie were working together again, Leslie tried to call things off, but found it difficult to resist. Neil wanted to get serious, and gave her a necklace for Valentine's Day, but he began to see that she and Tyler had some secrets they were hiding.
Neil had no more than taken up the reigns of Jabot again when Jack realized that his heart was with Jabot, not Newman, and left Newman in Adam's hands. When putting together his team to run Jabot, Jack hired Billy and Kyle, and Neil was made head of the new fashion division with Cane and Lily under him.
Leslie eventually broke down and admitted the truth to Neil about her past, that her father, Gus, was in prison for killing her mother, and that she and Tyler had changed their names as teenagers when they went to California to live with an aunt. Neil later stopped Leslie from leaving town after receiving a call on her cell phone from Gus, and talked her into going to see Gus in prison. Gus was eventually cleared and released from prison, but having nowhere to go, Leslie allowed Gus to live with her at her apartment. But it was not long before Gus died from a heart attack.
After Neil's apartment was ransacked and only a flash drive containing sensitive Jabot files was missing, a story about Leslie hiding her secret past hit the Internet on the GC Buzz page. Later another story about Lily and Cane appeared which had come from Neil's stolen journal. Neil was shocked when Kevin discovered that GC Buzz was a domain owned by Neil's own corporation NEWbiz Inc.
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