We want a world where people "deserve" the things they have/can-do; but I don't think we will ever get close to that (we sure can try tho)

It happens the same way in an individual level; the "wolf of wall street" (Jordan Belfortm) did a lot of illegal things; but despite being found guilty and forced to pay fines he is still better off for having done them (~10M offshore money and book/movie money among others).

Heck, it even happens in social interactions, for example kissing a random woman in the street without asking can give someone jail time (sexual harassment and what not) but if he is lucky she may fall for that; they may even get married later on.

I don't think the kiss example is a good comparison because if you go to jail you gain nothing, whereas banksters do.

I lead a department at a medium sized global business. I recently approached our internal counsel and external specialists about day to day legal issues my team encounters. I wanted to know: Can, Can't, Should, Shouldn't. All I got was a statistical probability of getting in trouble and a summary that stated do whatever, the chances of getting caught and the chances of that even mattering are nil. Better off doing what makes you most effective, even if that entails breaking the law.

When you look at it clinically it makes sense. Quite the slippery slope.

Everyone does the same thing in their personal lives.

"% chance of getting in trouble if I punch this asshole in the face?"

"% chance of getting a speeding ticket if I go 15 above?"

Is it really so much that the current environment rewards companies that take regulatory risks, or that regulatory risks are so pervasive you can't do business without them?

There is some risk of harm of bad dealing at almost every level, but we try to pay attention to the people with the most financial power because they have the greatest ability to do harm. And of course the more incentive there is to subvert the laws. Probably any simple view of this issue is wrong.