50 Cent, or Curtis James Jackson III, is thought of as one of the smartest entrepreneurs in the music industry. Following his rise to fame he decided to take his hard earned cash and invest in multiple business projects. From Vitamin Water to Ecko clothing, it seemed like the rapper knew what he was doing.

Now Jackson is making headlines for a different reason. After posting a sex tape of Lastonia Leviston online, Jackson was court ordered to pay $2 million in damages. In response, the rapper has filed for bankruptcy, claiming that his lavish lifestyle portrayed on the media is just an illusion. But, new documents seem to paint a different picture.

So how did one of Hip Hop’s smartest businessmen go bankrupt?

The newest bankruptcy documents filed this week showed that his monthly expenses amounted to nearly $108,000. And, with a monthly income of $76,000, of course he has been falling short. His expenses include; $72,000 a month for his house, $5,000 for gardening, $3,000 for wardrobe, $1,000 for personal grooming, and another $14,600 for child-support and to care for his grandfather.

He listed his assets at around $24.8 million, but his liabilities were over $32.5 million. Of his assets $500,000 were made up of cars alone, including a Rolls Royce. He did imply that he had to trade in two other cars for his Phantom. Small sacrifice.

50’s next hearing will be on Wednesday. And, for now, the fate of the “Get Rich or Die Tryin’” rapper lies in the hand of the bankruptcy court.