The prosecution also tried to undermine earlier testimony from one of their own witnesses — Jackson's ex-wife Deborah Rowe — by calling an investigator who said Rowe told him last year Jackson was a "sociopath."
The testimony on Tuesday came as the prosecution neared the end of its case.
Jackson, 46, is accused of molesting a 13-year-old boy at his Neverland ranch in February or March 2003, giving him alcohol and conspiring to hold the accuser's family captive to get them to rebut a damaging documentary about the pop star.
The detailed analysis of Jackson's multimillion-dollar empire was brought into the trial over vehement objections from defense attorneys who said it was irrelevant to the case and was based on hearsay statements contained in memos from various financial advisers.
CBS News Correspondent Steve Futterman reports that Jackson may be the king of pop, but he seems to not be able to keep a reign on his own finances.
There have been rumors about Jackson's dire financial condition for years, but this was the first time so many details were laid out in court, Futterman reports. A forensic accountant testified that as of 2002 and 2003 Jackson had massive debts.
Judge Rodney S. Melville instructed jurors they were not to consider the accounting figures "for the truth of the matter" but merely to show how the expert reached his conclusions.
Under questioning by Deputy District Attorney Gordon Auchincloss, forensic accountant John Duross O'Bryan traced Jackson's assets and liabilities from 1999 to 2004.
The witness said he obtained only one balance sheet, from June 30, 2002, and it showed Jackson with a net worth of negative $285 million. He said this included assets of $130 million and liabilities of $415 million.
He said the balance sheet was prepared on a tax basis and assets listed might actually have higher values.
"There was an ongoing cash crisis, not enough cash to pay bills," Duross O'Bryan testified.
He said he formed his opinions by reading through boxes of memos exchanged by Jackson's financial managers over the years, and he told of a warning to Jackson that if his overspending continued he might be forced to sell off his two greatest assets, the catalogue of his own songs and the Sony-ATV catalogue which contains rights to the works of numerous other artists including the Beatles.
The witness said even selling the catalogues would be problematic because that would incur a huge tax liability.
Defense attorney Thomas Mesereau Jr. said the catalogue was worth $1 billion in 2003, and there have been estimates it's now worth between $4 billion and $5 billion.