An administrative law judge should rule on the technical matters and if the legislative representatives of We the People have not done their job and closed loopholes, then the perp could get off scott free.

  Even worse, if he knows his rights, he'll demand a jury trial by his peers, exercise his  administrative, civil and fundamental rights (pesky things like habeus corpus and such...) and convince one juror to hold out against criminal conviction in such a matter.  Maybe a civil jury rules against him, he appeals and wins on a technicality, all of which points out the ambiguity in such cases, whether this  character or his potential cell mate who claims a tax loophole. 

  Funny, but the number of "loopholes" that corporate America claims when billions are made and they have zero taxes to pay, causes you no outrage what-so-ever, as you run crying about a guy avoiding a few dollars in income tax.  Perspective is lost and credibility too when invalid comparisons such as this are made.