As the world mourns the loss of pop music legend Michael Jackson, lawyers are burning the midnight oil trying to decipher the financial mess he left behind. What is coming to light is that,  despite the Jackson estate having hundreds of millions of dollars in assets and royalties, it also has hundreds of millions of dollars of debt.

Michael Jackson was a shrewd business negotiator. Back in 1985, he paid $47.5 million for ATV, which holds the publishing rights to some 4,000 songs, including about 200 Beatles songs. 20 years later, that catalog of songs, which is now co-owned by Sony, is worth $500 million.

There were also continuous sales of his 10 solo albums, including "Bad", "Dangerous", Off the Wall", "Invincible", and "HIStory". His best selling solo album, "Thriller", is currently in the Guinness Book of World Records for having sold the most copies ever, at a record 65 million copies. Additionally, there are the 16 albums that Michael produced while recording with his brothers.

Estimates of Michael’s total music and music-related revenues stand at $700 -$750 million. And yet, as recently as 2006, Michael was attempting to secure a loan of $300 million to pay off his debts.

Michael Jackson lived a lavish lifestyle marked by certain eccentricities. Neverland Ranch, a property which Michael purchased in 1987, was costing at least $4 million a year to maintain and staff. Michael also had a taste for rare antiques and art, as well as spur-of-the-moment privately chartered jet trips. On a yearly basis, Michael would spend as much as $30 million more than he earned.

All that debt was catching up with him. In 1995, Michael agreed to merge his ownership of ATV with Sony. However, in 2001, he again ran into financial trouble, and had to use his half of ATV to secure a $200 million loan from Bank of America. This loan had to later be refinanced to resolve the looming issue of insolvency.

In later years, Michael would face financial lawsuits and even the threatened foreclosure of his Neverland home. In order to stave off his creditors, Michael played a debt juggling act, paying off one debt by taking on another. Most notably, this occurred with Sheikh Abdulla bin Hamad al Khalifa, son of the King of Bahrain. The Sheikh claimed he had provided Michael with millions of dollars so that Michael could settle his debts. In return, Michael was expected to write an autobiography and record a new album.

As the debt continued to pile up, there were few options left to Michael. He could sell off his assets, including Neverland. He could declare bankruptcy. Or…he could attempt a glorious comeback, thus  generating some much needed cash.

Michael chose the comeback route. He signed on for what turned out to be a 50 run performance at the O2 Arena in London. Ticket sales started coming in, with at least 800,000 tickets sold. Stores geared up with extra solo albums and other memorabilia. The shows were to start this July 13th.

Michael, now 50 years of age, was practicing for the 50 run performance aptly named "This Is It". His schedule was grueling, but he was a perfectionist and wanted the shows to go off without a single mistake. It is anyone’s guess how long it had been since Michael had practiced with such rigor, since his last public performance had been 12 years ago.

There was another problem. Reports abound that Michael was taking daily injections of Demerol, which is a pain killer and a narcotic. Also, OxyContin, another pain killer, may have been used. These drugs are not meant to be taken constantly. If they are, they can lead to addiction, heart attacks, cardiac arrests, and other health problems.

Michael Jackson had originally signed on to do 10 performances at the O2 Arena. Somehow, that number kept expanding until it reached 50. Even for a man half his age, Michael would’ve been hard put to plan and execute so many performances. Appearing in ever more frail and ailing health, Michael’s backers even had him undergo rigorous health tests. He was declared healthy; the show would go on. After all, there were tickets already sold (to the tune of an estimated $75 million), many more tickets left to sell, and the millions to be made in comeback tour albums, singles discs, and coffee mugs. 

Well, we all know what happened. Michael evaded his creditors one last time. However, had he not had these creditors and his mounting debt to begin with, perhaps he’d still be alive today.