Found this comment on Reddit, helps explain to us layman:
CPA checking in...
This filing buys him the time he wants/needs to pay his debts. He's not "bankrupt" in the typical usage of the term.
He's filing chapter 11 bankruptcy; this is not bankruptcy as most citizens know it. The bankruptcy that most people know is Chapter 7 bankruptcy (or chapter 13 under certain conditions) and is a total reset where you are left with no assets and no debts.
Chapter 11 bankruptcy is typically known as a "restructuring" bankruptcy. Given the lawsuits they quote in the article, I would assume he does not have immediate access to the liquid assets necessary to pay his immediate debts. This filing is to protect his investments while his financial team develops the most appropriate plan to pay his lawsuit debts. Paying $20mm is not an emergency for someone worth $500mm; paying $20mm in the next 30 days for most people of significant wealth is an emergency--most of their wealth is in investments. Think Zuckerberg here... Net worth of ~40 billion. 24 billion of that is in Facebook stock. It's not easy to free up mass units of stock for their fair market value because selling off large units of stock tanks the stock value.
Yet the both have made more money than you could count to. If you are so much smarter, why aren't you richer? I bet Floyd and 50 have made more money selling socks and crappy bottled water than you will see in your lifetime.
Don't be fooled by Celebs filing Bankruptcy it is likely to get out of a bad deal or to avoid paying up for a Lawsuit he lost or a Lawsuit coming up that he knows he could lose. It likely has something to do with not paying SLEEK Audio $16-$17.2 Million for a Lawsuit he lost. On top of just losing a recent Lawsuit for $5 Million for leaking a Sextape. You file Bankruptcy to either get away with not paying them or you get them to settle to pay much less than you was originally suppose to pay.
Filing Bankruptcy can help protect assets you already have and other things.
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