????Was the King of Pop smart, lucky, or a little off about how he conducted his finances? Turns out, he managed to be all at the same time.

????By Richard Siklos, editor at large

????NEW YORK (Fortune) -- We all know that Michael Jackson was one of the greatest entertainers who ever lived. But when it came to how he conducted his business and financial affairs, was he smart, lucky, or mad? As depicted in the Fight Over Michael's Millions , he managed to be all at the same time.

????Repeatedly, people who worked with Jackson told me that although he had a shrewd sense of business, he had no appreciation of -- or concern about -- the value of money. He came into an unfathomable amount of it during the 1980s at the apex of his success, and he hit a double-home run when he parlayed $47.5 million into his half-interest in what is today Sony/ATV Publishing, which is now worth more than 10 times that.

????It's interesting that despite leaving his famed Neverland Ranch nearly five years ago and vowing never to return, Jackson never bought another home. My impression is that is because he only believed in doing things on an ever grander scale and he was biding his time till he could come back bigger than ever.

????This explains the apparent lunacy of Jackson, despite the crippling loans he carried, this year planning to buy a house in Las Vegas for close to $50 million and even having a $15 million advance for the house built into his contract with AEG, the promoter of his comeback concerts.

????According to Jackson's recent manager Tohme Tohme, Jackson's largesse extended to people he cared for -- he says Jackson agreed to buy a $600,000 motor home for his mother Katherine and asked that a $400,000 bracelet that he liked be bought and sent to one of his celebrity pals -- both in the past couple of years when he was on the brink of financial ruin.

????Yet, Jackson understood that he needed to make money to get out of hock. One of the many ironies in Jackson's tragedy is that he was poised to sell a warehouse full of his vast possessions at an auction in Los Angeles this past April. He called that off at the last minute and now, given the interest in Jackson since his death, his stuff is undoubtedly worth far more.

????Plus, some pieces are now about to start earning his estate money as part of a touring exhibition of his memorabilia slated to begin in London next week. (Go here if you want to see the catalogue from the aborted auction.) Whether the Jackson provenance is a plus or minus for the real estate value of Neverland when it is eventually sold remains to be seen.

????When it came to negotiating deals (which he often reneged on), Jackson could be sly. He understood that he had assets people coveted -- including proximity to himself -- and that he could find ways to moonwalk around financial disaster.

????Sony/ATV was a calling card that separated him from being a mere musical megastar. By following Paul McCartney's advice and buying up music catalogues, Jackson bet wisely on a segment of the music business that has actually grown over the past few years, as music gets licensed for new uses, like ring tones and advertising and TV shows like "American Idol" and video games like Rock Band.

????And whether he intended to or not, Jackson picked a business that did just fine -- if not better -- without him involved day to day. During the years Jackson was in the figurative wilderness, he was also an absentee partner at Sony/ATV. Until Sony secured more control over business decisions when it helped Jackson hold onto his stake in the company in 2006, it was apparently impossible to track down Jackson and get him to agree to things.

????With a freer hand, Sony was more easily able to make more than $500 million of acquisitions and bring in Martin Bandier, a music industry veteran, to build and run the Sony/ATV in early 2007. Last year, the company made around $65 million in operating profit on revenue of close to $500 million, insiders claim, and the business won an internal award at Sony (SNE) for its rich margins.

????Jackson cherished his association with the business and appreciated how Sony had helped him in his pinch, but he was also mistrustful of the Japanese conglomerate after falling out with his record label there a few years ago. It probably didn't help that the partners didn't hold a single board meeting between 2002 and 2007, and Jackson never bothered to meet Bandier in person.

????When he agreed to the comeback shows in London, Jackson wanted it known that he was going back to work for the benefit of his three children -- he and his youngest son, Prince Michael II (also known as "Blanket") even showed up in matching black suits when he went to meet Phillip Anschutz, the tycoon whose company, AEG, was to stage the concerts.

????Jackson explained that, more than the money, he wanted to show his kids what he had done in his heyday. But at the same time, his advisors say, he mused about a future when he would somehow buy back the other half of Sony/ATV and live off publishing riches in his big mansion in Las Vegas while making movies and doing other things.

????It was an impossible dream.