Despite what seemed to be a very well-kept and diversified portfolio of stock investments, along with several year's worth of endorsements, Curtis 50 Cent Jackson has filed for chapter 11 bankruptcy.

According to The Wall Street Journal, Jackson filed the order to the U.S. Bankruptcy Court in Hartford, Conn. just days after he was ordered to pay $5 million in punitive damages to Lastonia Leviston for the unlawful release of a sex tape. The AP claims, "A jury ordered the rapper-actor Friday to pay $5 million to a woman who said he acquired a video she made with her boyfriend, added himself as a crude commentator and posted it online without her permission."

Assets and debts noted on the filing both range between $10 million to $50 million. For those who may be unfamiliar with the U.S.'s handling of Chapter 11 Bankruptcy, it's not actually a measure to indicate if the party filing is completely out of money. Rather, it's commonly used as a business practice to reorganize the method of which the party pays its creditors over a different period of time. Unlike Chapter 7 or 13 bankruptcy's, Chapter 11 is usually designated for very financially viable individuals or companies (think Donald Trump) and is given usually an allotted amount of time to think of a functional reorganization to re-pay said debts. A successful Chapter 11 plan can lead to the filing party back on its feet relatively quickly.

The news comes only a year after Jackson cracked the top five on Forbes' Wealthiest Rappers list, with a net worth of $140 million. He will also be appearing in Jake Gyllenhaal's upcoming boxing movie Southpaw.