Documents filed in Connecticut Bankruptcy Court showed Jackson’s listed assets and debts to be in the range of $10 million to $50 million.
Jackson’s attorney was not immediately available to comment on the timing of the filing.
A sale of the rapper’s stake in VitaminWater netted him about $100 million after taxes when Coca-Cola purchased the beverage brand in 2007.
In a more recent venture, Jackson closed a $78 million deal at the end of 2014 with FRIGO Revolution Wear to promote men’s underwear.
But filing for bankruptcy doesn’t necessarily mean the Grammy award-winning rapper is out of money, according to Leon Bayer, a bankruptcy attorney at Bayer Wishman & Leotta.
“Chapter 11 is the drug of choice for celebrity debt problems,” he said. “You don’t have to be broke to file for chapter 11, but it could mean you don’t have good cash flow.”
Whether or not that is the case will be made more clear sometime in the 14 days Jackson has to file his debt payment plan or “schedules,” which could reveal intimate financial details.
“When he files schedules it’s going to show all the details of his debts, assets, even whether or not he paid his gardener on time,” Bayer said.
Intentionally or not, Jackson’s bankruptcy will also put a roadblock between the $5 million he was ordered to pay and the woman winning her sex tape case was set to receive.
“It tells them they aren’t going to get a check anytime soon, so why not sit back down at the negotiating table,” he said.
Jackson’s spending and business activity—including any salary drawn for himself—could be subject to the scrutiny and approval of bankruptcy court pending the review of Jackson’s filing.