How can one person spend $350 million? NYT tries to answer the question, by looking at Michael Jackson's financial history:
Just last month, Mr. Jackson — still swamped in debt, with his musical career in stasis and his personal life limned by scandal — agreed to that financial overhaul. It is likely to strip him of about half of his remaining stake in the catalog, which he has relied on as a financial lifeline for about a decade. According to executives involved in the restructuring talks, Mr. Jackson used the catalog, as well as copyrights to his own songs, as collateral for roughly $270 million in bank loans he took out to fund a spending spree that includes upkeep for his sprawling California ranch, Neverland, and other exotic luxuries.
Given how precarious Mr. Jackson's financial situation appears to be, it is unclear how long he will be able to retain his remaining stake in his prized music catalog. A reckoning appears near, and Mr. Jackson's ability to hold onto his fortune has proven to be as fleeting as stardom itself…
"I think that Michael never had any concept of fiscal responsibility, or logical fiscal responsibility. He was an individual that had been overindulged by those that represented him or worked for him for all of his life," said Alvin Malnik, a former financial adviser to Mr. Jackson and a former lawyer for Meyer Lansky, the late mob kingpin. "There was no planning in terms of allocations of how much he should spend. As a businessman, you can forecast your spending for the next six months to a year. For Michael, it was whatever he wanted at the time he wanted…
Others close to Mr. Jackson say that the performer's finances have not deteriorated simply because he is a big spender. They say that until the early 1990's, he paid relatively close attention to his accounting and kept an eye on the cash that flowed through his business and creative ventures. After that, they say, Mr. Jackson became overly enamored of something that ensnares wealthy people of all stripes: bad advice.
While Michael did spend a lot of money on art, property, and other expensive things for personal use, it is reported that he would put lavish amounts of money into his marketing schemes and video projects, in an attempt to revive his waning music career:
Mr. Jackson indulged in other pricey vanity projects, including what one adviser believes to be the most expensive — a 35-minute film called "Ghosts" that he co-wrote with the novelist Stephen King and shot in 1997 with Stan Winston, a special-effects whiz that cost well above $15 million. One person with direct knowledge of Mr. Jackson's spending said that the star paid a substantial portion of as much as $65 million on video projects in the mid-90's — outlays that contributed significantly to his financial problems.
And while he was spending millions on work projects, he was also as well as investing in questionable business ventures and borrowing cash for personal things:
Documents indicate that by late 1998, Mr. Jackson had already taken out and depleted a $90 million bank loan and Mr. Lee arranged a new, $140 million loan from Bank of America that was collateralized by the Beatles catalog and used to pay off earlier debts. Just several months later, the $140 million had evaporated and Mr. Jackson, fresh off of his divorce settlement with Lisa Marie Presley, obtained another $30 million line of credit from Bank of America. Mr. Lee said in court papers that in late 2000 he raised the original $140 million bank loan to $200 million, using part of that loan to pay down the $30 million credit line, which had been entirely tapped…
All the while, Mr. Jackson's spending ramped up. As described by several of Mr. Jackson's former associates, he routinely borrowed large sums of cash to pay for things he may not have been able to afford. Marc Schaffel, who formerly served as an adviser on Mr. Jackson's television projects, alleges in a lawsuit scheduled for trial next month that Mr. Jackson failed to reimburse him for outlays of more than $2.2 million, much of it in cash.
The rest of the article can be found here: