This strategy would also, if developed further, make legislative bodies impotent. If everyone could smooth out their risk profiles by betting on negative outcomes, then the only effect of any proposed legislation on people's behavior would be a transfer of wealth reflecting individuals' indifference curves (i.e. the outcome sets they are indifferent between). New laws would lose most of their ability to change behavior.
(Btw, why "User:Kevin"?)
This strategy would also, if developed further, make legislative bodies impotent.
How so? If someone recieves money when their current business becomes illegal, this doesn't mean that they'll carry on in the business, ignoring the change in law. In fact, it makes it easier for them to cease their current business immediately.
I may be missing some major point, so if so clarify, but it seems to me that this would in no way decrease the effectiveness of legislation at discouraging actions after it was enforced: all it would do is decrease the effect of THREATENED legislation (that has not yet been passed).