Michael Jackson "owed $500 million at the time of his death", according to court documents.
The King of Pop owed money to over 65 creditors when he died in 2009, according to paperwork filed on 21 June.
The legal documents include a petition from estate executors seeking back pay from 2018, which is related to the late singer's now $2 billion (£1.58 billion) estate.
The Thriller singer had "more than half a dozen lawsuits pending worldwide" and more than "65 creditors' claims" were filed in the Estate, showed the documents. This led to "additional lawsuits, of which several resulted in litigation."
Estate executors are now seeking reimbursement of "legal, negotiating and various other operating expenses" over the last six years.
"The Executors were able to renegotiate and restructure financing arrangements that existed at the time of Michael's death, at substantially reduced interest rates, enabling the Estate to avoid the loss of any assets to the lenders and ultimately to satisfy the encumbrances that existed at the time of Michael's death," the petition read. The paperwork states that the executors managing the estate must seek court approval every six months to receive 30% of their compensation, while they retain the remaining 70%.
Earlier this month, Michael Jackson's estate agreed to sell its remaining stake in a music catalogue to Sony Corp for $750 million. (£593 million). At the time of his death, the music catalogue was his most lucrative asset.
Michael died aged 50 of a cardiac arrest. This was ruled to be the result of a lethal combination of sedatives and anaesthetic propofol. In 2011, the singer's personal doctor, Conrad Murray, was found guilty of involuntary manslaughter.