• Michael Jackson was more than $500 million in debt at the time of his death in 2009, according to court documents filed this month

• The King of Pop's estate has filed a petition to be reimbursed for legal, negotiating and various other operating expenses from 2018

• Jackson owed money to more than 65 creditors when he died, according to the new filing

When Michael Jackson died on June 25, 2009 of apparent cardiac arrest in Los Angeles at age 50, he was over $500 million in debt, according to court documents filed on Friday, June 21 and obtained by PEOPLE.

The night before his death, the King of Pop ran through a six-hour dress rehearsal at the Staples Center in Los Angeles for his extended This Is It residency at the 02 Arena in London. As part of his comeback plan, he had written new songs and gone through many hours of grueling rehearsals to perfect the shows, which were scheduled to run from July 2009 to March 2010.

However, given Jackson's exorbitant spending habits, he desperately needed money to pay off his accruing debt of $30 million a year, according to the Los Angeles Times. The publication reported that certified public accountant William R. Ackerman, testifying as a defense witness on behalf of AEG Live in the wrongful-death trial in August 2013, offered a detailed look at the singer's finances, telling jurors that Jackson spent money on donations to charity, gifts, travel, art and furniture.

"He spent a lot of money on jewelry," Ackerman added in the downtown Los Angeles courtroom at the time. "He was tapped out."

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Michael Jackson onstage in Brunei in July 1996

As early as 1993, Jackson had accrued mounting debt, and by 1998, he owed $140 million, according to the publication. From June 2001 through June 2009, it was noted that Jackson's debt increased by about $170 million. Ackerman testified that interest on Jackson's loans also grew over the years, ranging from a little less than 7% to 16.8% annually.

According to The New York Times, Jackson used his stake in a song catalog that included the Beatles hits as part of collateral for about $270 million in loans from Bank of America. (The bank sold the loans in 2005 to Fortress Investment Group, a company that buys distressed debt.)

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Michael Jackson in Los Angeles in 1983

"He wanted people to see his work and not just talk about his lifestyle," Randy Phillips, the former CEO of AEG Live, told Rolling Stone in 2009. "Michael was a very smart marketing person. People say he was feeble and manipulated, but he was powerful and a manipulator. He was ready," Phillips told the publication. "He wanted to clean up his finances. He was ready to stop living like a vagabond and settle down and earn money again."