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.
As it turned out, Ross, who had been staying at Tuscon's ritzy Canyon Ranch, had a blood alcohol level that was nearly triple the state limit of .08. In February 2003, she was convicted of driving under the influence and sentenced to two days in jail, a year of probation and fines in excess of $800.
By all accounts, Ross was a good mother to her five children. She has three daughters with first husband and music business manager Robert Silberstein -- Rhonda, Tracee and Chudney Silberstein -- and two sons, Ross and Evan Naess, by second husband Arne Naess, a Norwegian multimillionaire.
Rhonda, however, did not learn until the age of 13, that her birth father is actually Berry Gordy, Ross' Motown boss.
The aspiring jazz singer told the New York Post in 1994 that she was shocked to learn the news. Gordy had always been a friend of the family and kept in touch with her.
"I've known him forever as a friend of the family. But we always did have a special relationship -- even before I knew he was my dad," she told the Post.
Jackson and Ross also had a special relationship, one of the most important in his life. Jackson idolized Ross, and some have said he even tried to emulate her.
Over the years, Jackson has had his obsessions with "it girls," including Elizabeth Taylor, Brooke Shields and Princess Diana. But Ross was always his idol. The two became close after Jackson signed on with Motown as a child.
When Jackson made his solo debut in 1971, he did it on one of Ross' TV specials.
In a 1981 Diana Ross TV special, Ross brought out Jackson's shy demeanor, teasing him about being "very sexy."
"You are embarrassing me," he replied, laughing.
They were so close, in fact, that some have even speculated that Jackson's plastic surgeries were done to make him look like Ross.
"Whether that was purposeful on his part has never been explained by M.J. when he was alive or anyone close to him. Certainly the parallel in their appearance was marked," said J.D. Heyman, assistant managing editor of People magazine.
Ross has yet to speak publicly on the death of her good friend, but she issued a statement shortly after he died.
"I can't stop crying, this is too sudden and shocking. I am unable to imagine this," she said. "My heart is hurting. I am in prayer for his kids and the family."
Jackson's infatuation with Ross began when they first met at Motown. She was the glamorous star of the Supremes, he was a 9-year-old performing prodigy.
Though it's been said that she discovered Jackson and his brothers, the Jackson 5, it was actually Gladys Knight and the Pips, another Motown act, who first saw them perform at the Regal Theater in Chicago and tried to get them an audition with Motown founder Berry Gordy. Motown artist Bobby Taylor got them the audition. But when the press release announcing the hot new group came out in 1969, it said Ross, the label's biggest star, had discovered the group while on tour.
Jackson played along with it. In an interview at the age of 10, he said, "I thought I was going to be an old man before being discovered, but along came Miss Diana Ross to save my career."
Jackson idolized Ross, according to biographer J. Randy Taraborrelli, who has written books about both superstars.
In his book, "Call Me Miss Ross," he wrote that Ross said, "I was older. He kind of idolized me and wanted to sing like me."
Some would say he even wanted to be her.
Taraborrelli wrote about one instance in 1986, when Jackson visited Ross backstage at Caesar's Palace in Las Vegas. When she returned to her dressing room, Jackson was putting on her makeup, transforming himself into Ross.
The writer also said Jackson once demanded that a chauffeur driving him around Beverly Hills that he address him as "Miss Ross."
In his autobiography "Moonwalk," Jackson called Ross "my mother, my lover and my sister all rolled into one."
Taraborrelli has said there was no sexual relationship between the two.
Nonetheless, in "Call Me Miss Ross," Taraborrelli wrote that Jackson was heartbroken when Ross got married for the second time to Naess. Jackson did not attend the wedding, telling Taraborrelli, "I was jealous, because I've always loved Diana Ross and always will."
Ross may have felt more motherly toward him. When Jackson moved to Los Angeles at the age of 9 to continue his recording career with Motown, he lived with Ross for a time.
The two stars shared a lot in common. Both started at Motown and became worldwide pop stars. Both earned diva reputations for their outsized lifestyles. And both were accused of selling out and turning their backs on their black heritage.
When Jackson collapsed during a rehearsal for a cable TV concert in 1995, Ross rushed to his bedside at a hospital in New York.
Biographer Brown said he wasn't aware that Ross and Jackson were close in recent years, but the fact that he included her in the will, he said, "just reiterates that she was his idol."