When Michael Jackson wrote his will in 2002 and named Diana Ross as the secondary caregiver to his three children, he was likely thinking about their longstanding relationship and the way she raised her own five children, not her erratic behavior, including two arrests, in recent years.
In his will, which was filed in court Wednesday, Jackson specified that if his mother, Katherine Jackson, his first choice to become guardian for his three young children, died before he did, Ross was to take custody of the kids. Omitted from the will was Jackson's ex-wife, Debbie Rowe, the mother of his two older children.
Jackson's three children, Michael Joseph Jr., 12; Paris-Michael Katherine Jackson, 11; and Prince Michael Jackson II, 7, known as Blanket, have been staying with their grandmother Katherine at the family compound in Encino, Calif., since Jackson's death last Thursday.
"Raising children was the most important role Michael Jackson believed he had, and to put down that Diana Ross would replace his mom, you can't have any greater honor," said Stacy Phillips, a family attorney not working for the Jacksons.
But Jackson biographer Stacy Brown said he was surprised by Jackson's choice, in part because of Ross' arrests for DUI and allegedly assaulting an airport worker.
"She's not the best of choices," Brown told ABCNews.com. "But if one of Michael's criteria was to have someone who wouldn't do it for the money, I think it's safe to say he firmly knew there was no way she would exploit his children," he added.
"Plus, Diana Ross raised all her children, Katherine raised all of hers," Brown continued. "Michael didn't want anyone who had small children. He wanted his children to get all the attention. You can't fault him for that. Michael Jackson loved his children. He was their best friend, they were his best friend."
While Ross's track record with her own children has been good -- "They came out pretty well. You can't argue that," Brown said -- her judgment in recent years hasn't been.
In September 1999, Ross was detained by British police after allegedly assaulting a female security officer at London's Heathrow airport. When Ross activated the airport metal detector, the guard tried to frisk her. Offended, Ross tried to return the favor, by patting the officer and reportedly saying, "This is how it feels to be fondled."
British police removed Ross from the airplane and detained her for five hours before allowing her to board another flight back to New York.
Later, she told interviewer Larry King, "I was angry. I am not excusing my behavior, but I guess we all react in different ways for different things."
Not long after that, Ross again stirred controversy when she was photographed touching the half-naked breast of rap star Lil' Kim at the MTV Awards.
"I was acting like a mother, to say, 'Why are you doing this?'" she explained to King.
But in December 2002, Ross was acting nothing like a mom when she was caught driving while drunk.
Tucson, Ariz., police had received a call of a white Pontiac traveling on the wrong side of the road. When Ross, driving a white Pontiac, pulled into a parking lot of a closed Blockbuster video store, a police officer approached her.
According to the police report, she failed to write out the alphabet correctly. She also fell before the count of seven when standing on one leg, then laughed about it. "Ha, ha, ha great," she said, according to the report.