By 1993 Neil Winters had married Drucilla Barber (Victoria Rowell), after she’d stolen him from her sister Olivia and the two fell in love (via Soaps in Depth). A year later, Dru was pregnant with her first child — there was just one little problem. Neil’s half-brother Malcom Winters (then Shemar Moore before he left the show) had come to Genoa City earlier that year and Dru had slept with him. She wasn’t sure which brother was the father of her baby girl, but she and Malcolm agreed that they would keep their affair a secret and have Neil raise the child regardless of the paternity.
Not long after Lily’s birth, Dru and Neil’s marriage hit the rocks. She wanted to work as a model and Neil preferred her to be a stay-at-home mom. The couple ended up divorcing and Drucilla moved away to Paris with their daughter.
In 2002, Drucilla returned to town with a 14-year-old Lily (Christel Khalil) in hopes that Neil could help her reign in their rebellious teenager. Dru and Neil reconciled romantically and were remarried by 2003. Lily and her mother had a strained relationship and it only grew worse when the truth about Lily’s paternity was revealed in 2006. The revelation led to Dru and Neil’s second divorce, though thankfully Lily was able to reconcile with her mother before Drucilla’s unexpected death in 2007.
Neil disapproved when Lily began dating Cane Ashby (Daniel Goddard) when she was 19 and he was 31 years old (via Soap Central). Though the couple would go through many ups and downs over the years, including two divorces of their own, the relationship produced two beloved grandchildren for Neil, twins Matilda and Charlie Ashby.
