Arguably, the penalties aren't really punitive enough, otherwise we wouldn't still have an industry of bleeding-edge tax dodges. I know -- professionally and no

Arguably, the penalties aren't really punitive enough, otherwise we wouldn't still have an industry of bleeding-edge tax dodges. I know -- professionally and not closely -- one guy who specializes in complex tax mitigation for the ultra-rich. His more outre schemes may get shut down by the IRS but, if you're a client of his, you're essentially gambling tens of millions of dollars that you can avoid paying hundreds of millions in top-level taxes. At the wealth level they're at, it's a perfectly reasonable roll of the dice.