The Playboy founder died on Wednesday at age 91. Madison became one of his live-in girlfriends at the Playboy Mansion in September 2001 and later became his main girlfriend while living with Kendra Wilkinson-Baskett and Bridget Marquardt, with whom she starred on the E! reality show The Girls Next Door. Madison and Hefner broke up in 2008. He wed for the third time in 2012 and ditched his multi-girlfriend lifestyle, while she herself got married a year later and had two kids.
On Thursday, she was photographed out and about her family in Los Angeles. She appeared expressionless while carrying a large beverage. On Friday, she was photographed receiving a Starbucks delivery at a Hollywood home, smiling widely while dressed comfortably in a purple Jack Skellington "Bone Daddy" T-shirt and black Harry Potter "Ravenclaw" sweatpants.
Madison did not leave the Playboy Mansion on good terms. She wrote about her and Hefner's relationship and breakup and her time at the house in her 2015 tell-all book Down the Rabbit Hole. She depicted him as manipulative, controlling and "a spoiled child in an old man's body."
Tiffany Rose/Getty Images
In her book, Madison also says that while she packing her things after their split, she came across a copy of his last will and testament, which had been placed on her side of the bed they once shared. She said the papers stated that she would receive $3 million after Hefner's death if she still lived at the Playboy Mansion after his passing. Hefner is estimated to be worth anywhere between $43 and $110 million and much of his fortune is expected to go to his four children.
After the memoir was published, he himself said in a statement, "Over the course of my life I've had more than my fair share of romantic relationships with wonderful women. Many moved on to live happy, healthy and productive lives, and I'm pleased to say remain dear friends today. Sadly, there are a few who have chosen to rewrite history in an attempt to stay in the spotlight. I guess, as the old saying goes: You can't win 'em all!"