Rapper 50 Cent has filed for bankruptcy protection just three days after he was ordered to pay $5 million in damages to a woman whose sex tape he posted online in 2009. (Reuters)

The news that rapper 50 Cent (whose real name is Curtis Jackson) filed for Chapter 11 bankruptcy Monday has us scratching our heads.

In May, Forbes reported that Fiddy was worth an estimated $155 million. He has multiple income streams; his music, partnership with Effen Vodka, SMS headphones and stake in Frigo underwear all help him rake in money. He’s also an actor and executive producer in the Starz series “Power.”

Friday, a jury ordered Jackson to pay Lastonia Leviston a $5 million settlement after he narrated her sex tape as a character named Pimpin’ Curly. The video was circulated on the Internet. Jackson denied uploading it himself, despite the fact that it appeared on his thisis50.com Web site. Leviston, who has a daughter with rapper Rick Ross, appears on the tape with a (now former) boyfriend who is not Ross. It seems she was a pawn in a dispute between Ross and Jackson. “At the time the video surfaced, Ross and 50 Cent were trading barbs via video, lyrics and interviews,” the Associated Press reported.

The timing of Jackson’s bankruptcy application is fueling speculation that he filed for bankruptcy to avoid paying the judgment.

[Behind the scenes of 50 Cent vs. Rick Ross: How a lucrative rap beef may end up costing Fiddy]

At any rate, the court documents, obtained and shared by the Wall Street Journal left us with more questions than answers about Mr. Cent’s financial situation.

Is he broke-broke? Or is he rich-people broke? Like Donald Trump-filing-for-bankruptcy-four-times broke?

It would appear Fiddy is rich-people broke. That is to say, he’s not liquidating all of his assets, which is what would likely happen if he filed for chapter 7 bankruptcy protection. Chapter 11 is a little more complicated.

In a statement to Billboard, his attorney William A. Brewer III wrote that “the filing allows Mr. Jackson to reorganize his financial affairs, as he addresses various professional liabilities and takes steps to position the future of his various business interests. Mr. Jackson’s business interests will continue unaffected in the ordinary course during the pendency of the chapter 11 case.”

“This filing for personal bankruptcy protection permits Mr. Jackson to continue his involvement with various business interests and continue his work as an entertainer, while he pursues an orderly reorganization of his financial affairs,” Brewer said.

Michael G. Kessler is a certified forensic accountant based in New York who has testified in multiple court cases as an expert witness. He reviewed the court documents, shared by the Wall Street Journal, from Jackson’s filing. The first thing he noticed was that there were only five pages.

“Normally you file an application and it has a tremendous amount of information in it, including who the debtors are and what the value of the debt is, what your sources of income are,” Kessler said. “It’s really good for investigative purposes to see these because it tells you the whole background on the individual.”

Searches on legal databases that would normally house the full documents did not return results for Jackson’s filing Monday.

But Kessler noticed other oddities, too.

“Even if they did a $5 million judgment against him, you would think that they would appeal that case so he doesn’t have to file for bankruptcy,” Kessler continued. “Right? When it’s on appeal, you can’t collect. So there’s a lot of things that don’t make sense to me as an investigator.”

What happened to all that Vitaminwater money?

Most of Jackson’s wealth came not from rapping, but from his stake in Glacéau Vitaminwater, which he sold to Coca-Cola in 2007 for $100 million. So what happened to all that money? Did it suddenly dry up like the state of California? Have 50’s pockets turned into the pecuniary equivalent of the Mojave Desert? Did he just blow all of it during a bad weekend in Vegas?

[How 50 Cent scored a half-billion]

We don’t know. In the documents provided by the Journal, Jackson states that he has between $10,000,001 and $50 million in assets, and between $10,000,001 and $50 million in liabilities. Clear as mud, right?

Here’s what we do know: Jackson has apparently been trying to offload his 19-bedroom, 52,000-square-foot mansion in Farmington, Conn. since 2007, when he listed it with an $18.5 million asking price. He bought it from Mike Tyson’s ex-wife Monica Turner in 2003 for $4.1 million, and reportedly put in somewhere between $3.5- to $6-million in improvements. In 2012, Curbed deemed it the “tackiest mansion listed for sale in New England.” Jackson slashed the price to $10.9 million in 2009, but apparently he’s still stuck with it because it’s listed as his home address in his bankruptcy application.

How is he going to feed one billion African children by 2016?

The one entity that won’t be directly affected by Jackson’s bankruptcy filing is the hungry children he pledged to feed after flying to Somalia and Kenya with the United Nations World Food Program.

It seems he actually wanted us to feed the children by purchasing his Street King energy drink. Every purchase of the beverage was supposed to provide a meal through the World Food program. In February 2012, Jackson told the AP he’d provided at least 3.5 million meals.

So how will he help the other roughly 996.5 million kids? The short answer: with other people’s money, obviously.