One person who can shed light on many of these topics is J. Randy Taraborrelli, a CBS News consultant and Michael Jackson biographer.
Michael Jackson had planned to kick off a 50-concert tour in part to bolster his finances. How badly did he need the money? Is that what was driving this tour?
"I'll have to say he needed the money badly, but Michael Jackson never did anything for monetary purposes," Taraborrelli told Dave Price on Friday in Los Angeles.
"He wasn't the kind of person to take a look at a bad financial situation and make a decision to do something about it. That's how he got into the bad financial situation. He was doing these concerts really because he wanted his kids to see him perform," Taraborrelli said.
"But the cold hard facts were some people say he was upwards of $400 million in debt. Was he that disconnected from reality? What was his existence like?" Price asked.
"You know, the difference between a couple million here and a couple hundred million dollars there for Michael Jackson didn't make much a difference. He lived a very extravagant lifestyle. He lived like a king. He was used to living like a king, and there was always enough money for Michael Jackson to do what he wanted to do with it. He never had concerns about finances. His advisers, of course, the people that were actually responsible for doing these figures, were always concerned. They tried to reason with Michael and tried to tell him that 'You're in trouble,' but it didn't really make an impact on him. He didn't really have those kinds of financial worries, especially after the trial," Taraborrelli explained.
"Now, Randy, we've heard so many different things from different commentators. Some have said this is an absolute shock. I'm stunned. A lot of people, though, have said, you know what, I expected this would be the end. Where do you fit? You know him perhaps better than most other people as a lifetime biographer," Price remarked.
"I think this is a shock. You know, obviously, he was in poor health for many years. I'm happy when I think about the last four years of his life, since the trial in Santa Maria that we covered, the molestation trial because I think he found a sense of peace in the last four years. He reprioritized his life so that his concerns weren't about his career and weren't about money but were mostly about his family and his children. So he had that time in the last four years to really devote himself to his kids. I'm happy to see that that became his focus in recent years," Taraborrelli said.
But Taraborrelli doesn't know if Jackson's legacy will always be marked with an asterisk. "I don't know. Time will tell. As the pages of history turn, whether we will think of Michael Jackson the way that he would want us to think of him, as the King of Pop, or whether he will have the asterisk that you talk about having to do with child molestation and all the scandal. I personally think that the music will prevail."
Looking at Jackson's eccentricities and lifestyle, where there parallels to other rock legends who died early, like Elvis Presley?
"It's interesting because we're standing here in front of Michael's home in Encino, and Michael Jackson still owns this home. I remember many times in the 1980s coming here and talking to Michael Jackson about Elvis Presley, and he'd always say that he felt that he wanted to be able to achieve the heights that Elvis had achieved, and he wanted the King. Of course, Elvis was the King. So Michael came up with the King of Pop. That's how that sort of evolved," Taraborrelli said.
"And there were a lot of similarities in the sense that they were surrounded by people, often maybe not the best people who often took advantage of them, but others who tried to help them as well. And both Elvis and Michael were the kinds of guys who didn't often listen to advice. They were very self-reliant and independent of people who, artists who did things their own way," he added.
What about the stranger aspects of Jackson's life, like the hyperbaric chambers, or buying the elephant man's bones?
"Well, you know, most of that wasn't even true. Most of that was publicity that Michael put forth himself in order to create this sort of sensational image in the media at a time in the 1980s that he felt that he wanted to be thought of as controversial and eccentric. Of course, then eventually the media began creating its own stories about him and it snowballed. But back in the beginning, the hyperbaric chamber and the elephant man's bones and the shrine to Elizabeth Taylor and all the things we know so well, those were fictions that came from Michael Jackson," Taraborrelli said.
What next for Jackson's children and his music, once the mourning ends?
"You know, Dave, it's anybody's guess at this point. I mean, no one expected this to happen. I hope that all of that is worked out in different insurance policies and in Michael's will. But I think that what we're going to see, just based on Michael Kackson's history, is a lot of controversy in the months and years to come about who gets what and where the children will be raised," Taraborrelli predicted.
"And if he was disconnected in reality, planning for the future, it may be a very sloppy process to get to the bottom of all this," Price remarked.
"I think that's likely, yes," Taraborrelli said.