As we speak, the Attorneys for Manhattan and the State of New York are investigating a high net-worth individual for allegedly engaging in clever ways to avoid taxes and other regulations using activities that are legal when engaged by themselves in good faith, but when used in conjunction with each other in bad faith, may be criminal.

The problem with “gaming” any system involving state-level entities is that they always have the power to retroactively look at your behaviour and declare that there is a pattern that amounts to criminal behaviour, even if none of the actions taken in isolation would be considered criminal.