Trip Hawkins, a founder of EA and the CEO of social and mobile game maker Digital Chocolate apparently owes the Internal Revenue Service $20 million. According to a Forbes report, Hawkins tried to use a personal bankruptcy to nullify the debt but a judge rejected it. U.S. District Court judge Jeffrey S. White upheld a lower bankruptcy court ruling related to tax shelters Hawkins has used to hide the personal wealth he gained from founding Electronic Arts nearly three decades ago.
Judge White said in his ruling that Hawkins knew he was insolvent after the IRS disallowed his tax shelters but "continued to spend money extravagantly with knowledge of his (federal and state) tax liabilities." The judge added that "Hawkins planned to defeat his taxes via bankruptcy and continue living the lifestyle to which he had grown accustomed."
You can read a decent accounting of Hawkins’ case on VentureBeat. The short story is that, according to Forbes, Hawkins went out of his way to avoid paying his IRS debt and paid very little of it down while still living an extravagant lifestyle.