The Tribune Co, owners of the LA Times, are in tax court trying to defend an inherited 1998 Times-Mirror transaction that cleared about 2 billion dollars cash money, but on which they paid no income tax. One wonders if Times-Mirror used Irwin Schiff's theories of income tax avoidance, but no, it was all vetted by Gibson, Dunn & Crutcher. Surely no fools they.
Gory details are all here in the LA Tax Avoider, but what it seems to be is that Times-Mirror sold some properties for 2 billion dollars. But they didn't get the money for their shares, quite -- a new LLC was set up holding just the cash and they traded their shares for shares of the new LLC in a tax-free exchange. So they only completely controlled 2 billion dollars rather than owning 2 billion dollars. Neat stunt. The IRS is asking for $915 million in back tax and penalty.
Note: for anyone considering the same thing for your business, the IRS has issued a don't-ever-try-this-crap-again letter.