Walter and Lillie Belle Barber had two daughters who were as different as night and day, and bitter rivals. Older sister Olivia could do no wrong. Younger sister Drucilla could do no right. Their mother, Lillie Belle, admitted many years later that Dru was an unwanted child, the result of husband Walter's drunken lust. It was no wonder that Dru ran away as a teenager and spent years on the streets racking up a criminal record.

Nathan Hastings, detective with the Paul Williams Detective Agency, caught a shoplifter while working security for Fenmore's Department Store, the same Drucilla Barber. Nathan ended up talking the judge into releasing Dru into his custody and took her in once he realized another thing they shared - Nathan was once illiterate too. Nathan taught Dru to read and be more ladylike, and eventually Dru fell in love with him. But lo and behold, who was Nathan's girlfriend? Dr. Olivia Barber, Drucilla's "perfect" sister. The sisters were reunited, but it was obvious no love was lost between them. Nathan explained that his heart was with Olivia. Dru plotted to win him away by seducing him, but that didn't work. Olivia informed their parents of Dru's presence in Genoa City. They came to see Dru, but were rebuffed, so returned home.

Pushed by Olivia to produce her mystery "boyfriend", Drucilla talked Jabot executive trainee and Stanford MBA graduate, Neil Winters, into playing the part. Neil ended up falling in love with Olivia himself. Olivia decided that Dru was setting them up, so moved up her wedding date. This was the year of the grand masquerade ball. Olivia had to work, so Nathan dressed as an Arabian and took Dru dressed as the Firebird ballerina. Nathan and Olivia married with Dru as reluctant 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 with the well-educated Neil Winters. Neil supported Dru in her rise to ballerina stardom. But 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.

A pregnant Olivia was found to have ovarian cancer, but refused to abort the baby to save her life. After the birth, Liv was to have a hysterectomy, but it and the cancer subject was dropped. But in later years they tried to have another baby. Nathan Jr. "Nate" was delivered early to save Liv's life.

Shortly after Dru and Neil were married at the Chancellor Estate, Lillie Belle left Walter and showed up in Genoa City. She stayed with Liv and Nathan, and drove a huge wedge between them with her bizarre behavior due to clinical depression. Dru tried to talk Lillie Belle into staying with them in hopes of giving Liv and Nathan space to repair their marriage. But as always, Dru's mother rebuffed her in favor of her chosen daughter Olivia. Walter ended up claiming his wife and returning home with Lillie Belle in tow.

Neil's black sheep half-brother Malcolm suddenly showed up in Genoa City, intent on patching up differences with Neil. Neil was convinced that Mal was only there to freeload, but Dru got Mal a job at Blade's photo studio which helped convince Neil he was wrong about Mal. One night Dru over-medicated her cold and ended up making love with Malcolm, mistaking him in her stupor for husband Neil. Mal had secretly been falling for 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, considered abortion. But when her doctor told Dru that her former life on the streets had left her with a condition that made it lucky she had conceived, let alone ever would again, she reconsidered. Dru and Mal decided the baby would remain Neil's no matter what, and only they and her sister Olivia would know the incident had ever happened.

Meanwhile Nathan and Olivia were still on the outs since Olivia took her mentally ill mother's side against Nathan. So Nathan began an affair with the beautiful Keesha Monroe. Olivia became suspicious, and both Dru and Neil tried to caution Nathan after they caught him with Keesha. Each time Nathan tried to end the affair, Olivia did something to drive Nathan back to Keesha's arms. Nathan finally ended the affair, and he and Liv began trying for another child. Just as Keesha was falling in love with Malcolm, he found out about the affair with Nathan and dumped her. Then Keesha began getting persistent calls from old boyfriend Stan, who later died of AIDS. Keesha went to Dr. Liv, turned out to be HIV positive, and had to tell Nathan. It was about this time that Dru decided to tell Olivia about Nathan's affair with Keesha. Liv was furious, not only that Nathan had betrayed her, but had also endangered her and Nate with HIV. She kicked Nathan out and forbade him to ever see their son again. All 3 of them were HIV negative, but Keesha was doomed now with full-blown AIDS. The compassionate Malcolm began seeing her again, helping her through the difficult times as she grew weaker and thinner, and would have otherwise been left all alone to die. Malcolm cared for her so, he brought her flowers and a veil and married her on her death bed so she could at least die happy. Nathan became desperate to see his son, and ended up kidnapping him. Life on the run was rough on Nate, so Nathan finally did the right thing, and was returning Nate to Olivia when he was struck by a car and killed.

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 he 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 caved in and they reconciled. When Dru realized that Neil was actually bent on keeping Dru pregnant and unable to model she started on the pill 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 deception 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.

Malcolm and Olivia were married, and Nate was thrilled to have the exciting and fun-loving Malcolm as his new "daddy." But eventually Liv began spending too much time at the hospital and not enough time on her marriage. Malcolm and Nate's nanny Julia were raising Nate. Olivia suddenly began being suspicious of Malcolm over nothing. When Malcolm's old love, singer Callie Rogers, arrived in town, Liv was convinced they were resuming their romance. Liv obsessed over Malcolm so, she ended up driving him to Callie, who had never stopped loving him. Malcolm tried to patch things up with Liv and convince her she was wrong about him, but Liv suddenly decided she didn't know if she wanted Malcolm or not. Her mind was on Malcolm's brother Neil, the man to which she was always drawn and much more suited. Much to Nate's disappointment, Malcolm asked Liv for a divorce and moved out. Liv made a play for Neil, but Neil was shocked and rebuffed her. So then, of course, Liv wanted Malcolm back and refused to let him go. Malcolm asked Callie to move in with him, Liv accepted the end, and the divorce did happen. Callie kept putting off marriage to Malcolm because, as it turned out, she was secretly married to her mobster manager Trey. When Malcolm was beaten to a pulp by the mobsters for "messing with Trey's wife", he broke it off with Callie. Of course, Liv found out and accused Malcolm of putting little Nate in jeopardy.

Then the always work-obsessive Olivia started getting symptoms she refused to recognize and ended up on her deathbed with aplastic anemia. She further alienated Malcolm when she changed her will so that Neil would raise Nate should she die. Dru returned to Genoa City with Lily in tow and donated necessary bone marrow to save Olivia's life. Olivia's near-death changed her holier-than-thou attitude, but it was short-lived. Then Olivia decided that Mal was not a fit role model for her son, refused to let them see each other, and set her sights on Neil. Malcolm sued for visitation and won.

Malcolm was presumed dead from an accident on a photo shoot in Kenya, and since Neil was hitting the bottle heavily, Liv, forbade him to see her son Nate. Liv's best friend Ashley's husband Brad Carlton began playing father figure in Nate's life.

Olivia's best friend, Ashley, faced the biggest crisis of her life: the discovery that she had rapidly spreading breast cancer. She has finished undergoing radiation and chemotherapy treatments and has lost her hair. The stress involved affected her relationship with her husband Brad, and Ash drove him into Olivia's arms. Brad was wise enough to stop it at one kiss, but Liv had a hard time forgetting -- especially once she uncovered Ashley's secret -- that Ashley's daughter, Abby, was fathered by theft of Victor Newman's sperm. Liv and Dru coerced Ashley into telling Brad the truth - or they would. Ash did, Brad was furious and left. Only days later, he and Liv made love. Then Ashley discovered she was pregnant with Brad's child. They have now reunited, and Liv is left out in the cold. Liv turned to her sister's spurned boyfriend, Psychiatrist Wesley Carter, and they became engaged. But somewhere along the line, Wesley disappeared back to Paris, and the engagement was broken.

Three years after he was declared dead, Malcolm has shown up in Genoa City, very much alive, sporting cornrows and a bad attitude. Malcolm is out for revenge against the brother who he thinks stole his fiancé and left him for dead in Kenya. Malcolm explained that a family took him in and nursed him back to health, then he ended up having to take care of them. But now mostly he returned to see Nate again. Olivia is resentful that Malcolm didn't make himself known to Nate as soon as possible, sparing him the devastation of his death, and is making Malcolm wait to reveal himself until Nate returns from boarding school at the end of the semester. Until then, Olivia convinced him to stay in her extra bedroom. But both Malcolm and Liv left town before that ever occurred.

Olivia moved to Africa and took a position with "Doctors Without Borders" a humanitarian aid group. In April of 2007, Sharon told Drucilla she was being blackmailed by Phyllis over her affair with Brad Carlton. When Sharon and Phyllis began fighting on the edge of a cliff during a NVP photo shoot, Dru intervened. When all lost hold of the cell phone they were fighting over, they lost her 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 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. Olivia remembered what a precocious child Dru had been, and how she had showed her love for Liv when she donated needed bone marrow when Liv was once on her deathbed. Sharon remembered her brutal honesty and her one-of-kind hats. Devon recalled that before Dru came into his life, no one had ever believed in him, and how she forced him through her love to believe in himself. Lily said Dru was the kind of woman who did it all; career and family, and was her role model. Neil believed Dru was still alive and said he was not going to give up looking for her, called her loyal and passionate about life.

In October 2008, Lily went to visit Liv in New York City while she was lecturing there for Doctors Without Borders, and returned to Genoa City with her. Olivia mentioned that her son Nate was now attending Johns Hopkins University Medical School. She 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 and has given her a ring. Much as Olivia likes Karen, after meeting Tyra and seeing how much chemistry she and Neil have, she advised Neil that he was marrying the wrong woman. 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 New Year's Eve 2008 at Indigo with Victoria as Matron of Honor and Victor arriving last minute to be Neil's Best Man, with Olivia still hoping Tyra would interrupt the wedding by declaring her love for Neil. Neil and Karen went to court the next day and 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. Neil and Karen eventually divorced when she found out that Tyra and Neil had a one night stand.

Lily started experiencing pain and Devon rushed her to the hospital. Olivia diagnosed her as not pregnant, but instead a mass was found 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, and stashed him in Murphy's trailer home that Billy had just bought as a rendezvous for them. 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 to do a hysterectomy, but that luckily some eggs were saved. They were later used so Mac could be a surrogate mother of twins for Cane and Lily.

In April 2010 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 as each tried to be a doting father to Lily.

A sonogram confirmed that the twins Mac was carrying were boy and girl. Olivia told Lily, Cane, and Mac about a clinical trial that would take amniotic fluid from the babies to give Lily more immunity to fight off the cancer, but both Lily and Mac turned it down fearing it may harm the babies. Instead Lily left for France with Olivia to try another experimental procedure. Cane could not go with her as he would not be allowed back if he left the country. Cane then decided to sue Mac for the right to take the placenta fluid against their wishes. A copy of Lily's will arrived in the mail shortly after she left where she specified that in the event of Lily's death, she wanted Cane and Mac to have joint custody of the twins. Mac was not sure how to handle the news since she had been trying to distance herself from the babies she carried so as not to get too attached to them, and not so hard to give them up. After Lily's procedure failed, she returned and took part in the hearing, but when Cane saw her emotions and frailty on the witness stand, he dropped the lawsuit. The next day, Mac went into early labor, the twins Charlie and Matilda (Matty), were born two months premature, and their amniotic fluid was saved for Lily's treatment. Lily and the twins stayed in the hospital all growing stronger, as she got her treatments. Meanwhile Mac shared with J.T. her guilty regrets and missing the babies.

Lily was released from the hospital and welcomed home by the family who had unpacked all the baby gifts, and had their house all ready for them when they could come home. "Family" also included Sofia Dupre, a former sorority sister of Oliva's when they attended Seton Hall University, who was Malcolm's fiancé. Cane and Lily visited the babies often, as deportation loomed closer for Cane once she got well. But Sofia saved the day by convincing Tucker to approve Cane as liaison with their corporate partner where Cane grew up in Canberra, Australia. Because Cane was uniquely qualified he obtained an eight month work visa. Cane and Lily eventually brought the twins home, and Lily's health continued to improve. Lily asked Mac to be Godmother to the twins. When she turned her down explaining that she was getting too attached to them, Lily asked Traci, and she accepted in memory of Colleen. Devon felt honored to be the twin's Godfather.

In February 2011, Justin Barber welcomed his cousin, Olivia to Los Angeles. She happened to be in town and had gladly accepted his wedding invitation. Bill Spencer told her that she looked familiar, but Olivia had no recollection of them meeting. (An inside joke, as actor Don Diamont had played Brad Carlton, and Olivia's lover, on Y&R for many years. The bride, Donna Logan, played by actress Jennifer Gareis also played Grace Turner on Y&R for many years.) Bill commented on Olivia's beauty and joked that Olivia and Justin could not possibly be related to one another. When Bill teased that Justin had fallen for "the ball and chain," Olivia appeared angry and found no humor in Bill's teasing. Bill toasted the newlyweds and Olivia asked for a turn to toast thanking everyone for their hospitality.

Later that month, Olivia attended the funeral of her niece Lily's husband, Cane Ashby. Her son Nate joined her, who was also in town from Boston where he was a surgeon and rheumatology specialist.

Malcolm and Sofia were married, and Sofia discovered that she was pregnant on her honeymoon. Seeing Neil and Sofia together after the honeymoon, 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. Sofia spoke to her 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. The baby, named Moses, turned out to be Neil's so Malcolm divorced Sofia and left town.

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. But the marriage ended in divorce, and Sofia and Moses moved to New York City.

On April 23, 2019, Lily was released from prison, and Neil was there to welcome her. They traveled to Genoa City to attend the grand opening of Society, a new restaurant venture by Devon and Abby Newman, featuring head chef Lola Rosales. Neil felt exhausted and laid down for a nap upstairs at Devon's penthouse, promising to meet them there later. When Neil failed to show up, Devon went home to check on him. Devon came down his stairway in tears, having discovered that Neil had died of a stroke in his sleep. Everyone in Genoa City Neil whose life Neil had touched was saddened and shocked by the news of the death of their friend. Family and friends gathered for Neil's funeral in tears, where his foster daughter Ana sang "Amazing Grace". They shared remembrances and stories of how Neil had touched their lives and made them better. Olivia was unable to attend, but through her son Nate sent a message that Neil was with Dru again, united forever. Everyone then gathered at Devon's penthouse to celebrate Neil's life, reminiscing, honoring, and playing his favorite jazz. Malcolm took a group photo. He ended it with a toast; "to Neil Ellis Winters, music lover, businessman, philanthropist, humanitarian, best friend, father, grandfather, best brother you could ask for." Neil's will was read a month later by Michael Baldwin. Olivia was left a $100,000 donation to Doctors Without Borders and a sculpture.