In 2003, Jackson was arrested on charges that he molested another 13-year-old boy. The 2005 trial, which ultimately ended in an acquittal, brought to light more details of Jackson's strained finances.
One forensic accountant testified that the singer had an "ongoing cash crisis" and was spending $20 million to $30 million more per year than he earned.
In March of last year, the singer faced foreclosure on Neverland. He also repeatedly failed to make mortgage payments on a house in Los Angeles that had been used for years by his family.
In addition, Jackson was forced to defend himself against a slew of lawsuits in recent years, including a $7 million claim from Sheik Abdulla bin Hamad Al Khalifa, the second son of the king of Bahrain.
Memorabilia auctions were frequently announced but became the subject of legal wrangling and were often canceled.
Time and again, however, Jackson found a way to wring cash out of high-value assets, borrowing tens of millions at a time or leaning on wealthy friends for advice, if not for money.
Al Khalifa, 33, took Jackson under his wing after his acquittal, moving him to the small Gulf estate and showering him with money.
In his lawsuit, Al Khalifa claimed he gave Jackson millions of dollars to help shore up his finances, cut an album, write an autobiography and subsidize his lifestyle -- including more than $300,000 for a "motivational guru." The lawsuit was settled last year for an undisclosed amount. Neither the album nor book was ever produced.
Another wealthy benefactor came to Jackson's aid last year as he faced the prospect of losing Neverland in a public auction.