Over the years, the IRS has tried to crack down on such deals. In 2006, the agency declared that including a share loan meant these types of transactions were sales, triggering an immediate income tax obligation. In McCombs's case, his lawyers contended that the share loan was separate from the first part of the transaction, and thus didn't transfer the so-called "benefits and burdens" of owning the stock. He settled his case for $23 million in back taxes plus interest.
In 2010, a U.S. Tax Court judge found Philip Anschutz, the entertainment, oil and media investor, owed $94 million in taxes after he used transactions similar to the ones used by McCombs. Anschutz, identified by Forbes as the 39th richest man in the U.S., is appealing the decision.
'More Hostile'
"The IRS shifted its view and threatened a legitimate business practice and that will have a dampening effect on investment," said a spokesman for Anschutz.
The IRS has "gotten more hostile toward these transactions over the years," through its various technical pronouncements and litigation, said Willens, the accounting analyst. Since 2006, such transactions haven't included the interim loan of shares to the investment bank, he said.
"It's still desirable to defer the tax and wind up with an interest free loan from the government," he said. "Chances are you don't get audited and if it does get challenged the odds are good you'll have a settlement for some fraction of the amount you saved. Who wouldn't want that?"