He lost a lot of money fighting the molestation cases. He also lost income because of all the negative publicity following a nasty trial. He also spent money on his bizarre physical transformation, which was always under scrutiny from the tabloids and the media. Sponsors who had at one point been clamoring for Jackson were now turned off by his private life.
Companies like Pepsi and sneaker brand LA Gear backed out of agreements with him. He was losing control over his finances. A divorce settlement with Lisa Marie Presley helped push Jackson to use his earnings as collateral for loans increasingly. Also, Jackson spent his money faster than he was earning it. He spent millions of dollars maintaining his park at Neverland Ranch in California, which was complete with a zoo, movie theater, and fairground.