Born June 25, 2010
Announced he was 6 years old in 2016
Morphed into teenager May 24, 2017, said to be fourteen
Student at Walnut Grove Academy
Summer job as lifeguard at Genoa City Athletic Club pool
House at 1101 Lavetta Terrace
Lily Ashby (mother)
Mackenzie Browning Helstrom (surrogate mother, godmother)
Cane Ashby (father)
Matilda Ashby (twin sister)
Sam Ashby (half brother)
Drucilla Barber (grandmother; presumed dead)
Genevieve Atkinson (grandmother; presumed dead)
Malcolm Winters (grandfather)
Colin Atkinson (grandfather)
Samantha Atkinson (aunt; deceased)
Caleb Atkinson (uncle; deceased)
Devon Hamilton Winters (uncle by Neil's adoption of Devon, godfather)
Moses Winters (uncle, son of Neil)
Nathan Hastings Jr. (uncle, son of Olivia)
Olivia Barber (great-aunt)
Neil Winters (great-uncle)
Lillie Belle Barber (great-grandmother)
Walter Barber (great-grandfather)
Mamie Johnson (great-grandaunt)
Zoey (dated, kissed)
Lily Winters married the Australian Cane Ashby in 2009. He was 12 years older than Lily. Lily became a model for Jabot Cosmetics, and Cane was a bartender at her father's club Indigo. After one miscarriage, Lily was diagnosed with ovarian cancer and had a hysterectomy. But luckily she had the foresight to harvest some of her eggs. Lily's best friend Mackenzie volunteered to be surrogate and soon became pregnant with twins Matilda and Charlie, who were born two months premature. Lily asked Mackenzie to be godmother to the twins, and Lily's adopted brother Devon became their godfather. Cane and Lily broke up numerous times, divorced and remarried, mostly due to Cane's screw-ups and the lies he told to cover them up, usually aided by his father Colin, and some infidelity on both sides. Except for the time that Colin kidnapped the twins and Cane faked his death, they still managed to keep a family atmosphere for the twins to grow up in.
One year when Lily and Cane were split up, the annual Delia Halloween costume party benefit was held at Top of the Tower. A fire broke out on the floors just below, cutting them off from the floor where her children were having their own party. They were rescued from the roof by helicopter and Lily was reunited with the twins who had been led out the front door.
Cane agreed to come home for Christmas eve and morning with the twins, staying in the guest room. Neil and the kids planted some mistletoe, then got the Ashbys to kiss underneath it. Months later, they reconciled.
In late 2016, Neil was playing basketball with young boy grandson Charlie, but by May 2017, Charlie and Mattie had morphed into teenagers and were sophomores attending Walnut Grove Academy. Charlie was popular and confident, and Mattie was smart, shy, and spectacled. Charlie got a summer job as a lifeguard at the Genoa City Athletic Club rooftop pool. Charlie was very charming to the Athletic Club guests, especially one pretty bikini-clad woman named Juliet.
Earlier that year, Cane had gone to Japan where he and a coworker named Juliet had gotten drunk, and he'd gotten her pregnant; both were subsequently fired. Juliet filed a sexual harassment lawsuit against Cane, so the twins had to be told about their impending half-sibling. They were shocked and appalled. When Charlie realized who his favorite customer Juliet was, he told her that if she were drowning, he would pull her out because it was his job, but he wanted nothing to do with her or her kid. After Lily discovered that Cane had used most of the twins' tuition money to pay off a blackmailer, Lily threw Cane out. Feeling guilty and hoping to win Lily back, Cane sold his car and paid the Walnut Grove tuition for the twins.
Meanwhile, young singer/musician Reed Helstrom was dating a fan named Zoey. Reed caught her kissing Charlie Ashby, so Reed and Zoey split up. Reed then became intrigued with Mattie. They began hanging out together when she could, and she would go to see him perform at the Underground. Finding out that her twin brother was Charlie, the guy who had broken up Reed and Zoey, and that Reed was the son of Victoria, who had fired his father, caused the two young men to bicker every time they met. However, once Mattie and Charlie discovered the truth behind Cane's firing, Charlie and Reed called a truce. But when her parents found out, Mattie was forbidden to see Reed. They began meeting on the sly, had their first kiss, with Charlie often covering for her absence. Cane caught them, but after Lily decided to divorce Cane she and Victoria removed the restriction. The twins were devastated by the divorce news, but understood. Charlie was disappointed further when he was not chosen for the football team. But when her parents found out, Mattie was forbidden to see Reed. They began meeting on the sly, had their first kiss, with Charlie often covering for her absence. Cane caught them, but after Lily decided to divorce Cane she and Victoria removed the restriction. The twins were devastated by the divorce news, but understood.
On Halloween, Reed borrowed the key to The Underground from Noah and he, Mattie and Charlie brought their friends intending to have a party. But when they heard Nick arrive they sent their friends home and hid in the store room. Not long after Nick left they realized the place was on fire and they were trapped. Mattie called 911 while Reed called Billy for help, and Charlie left a voicemail for Cane. Billy got inside and rescued them, they got out, but when the building collapsed, Billy’s leg was pinned. Jack arrived, and emotionally insisted on going in. He talked to Billy about forgiveness, and they walked out together with Jack smiling and Billy limping. Lily was reminded why she shouldn’t have allowed Mattie and Reed to see each other again, and Mattie was grounded.
Juliet went into labor, her baby was born via c-section, but Juliet died in childbirth. Cane and Lily named the baby Sam in honor of Cane’s deceased sister Samantha. Sam had a serious heart problem, his medication no longer working, he required cardiothoracic surgery.
After Cane surprised Lily in Paris where she had gone on a business trip, they reunited and Cane moved back home with Sam. Charlie accepted it readily, but Mattie was hesitant to forgive him, and Lily had a hard time dealing with Sam being there, but both gave it their all for the sake of the innocent baby.