Reuters, Odds Favor IRS in Supreme Court Tax Cases: Study, by Lynnley Browning:

The odds are stacked against corporations whose disputes with the tax-collecting IRS go all the way to the Supreme Court, a new study found.  [Joshua Blank (NYU) & Nancy Staudt (USC)), Corporate Shams, 87 N.Y.U. L. Rev. __ (2012).] …

The government won 61% of the 137 cases heard by the Supreme Court from 1909 through 2011 that involved allegations by the federal government of abusive tax-motivated transactions by corporations. …

The government’s chances of prevailing in cases of alleged abuse increase when there are discrepancies between a corporation’s internal books and its returns filed to the IRS, and in instances when a corporation claims it is owed a refund but has not been audited or challenged by the IRS.

The presence of one of two factors appears to give corporations the upper hand: the presence of third parties, such as partnerships, that are directly involved in the economics of the disputed transactions; or complex transactions that contain multiple financial steps.