There are many criticisms of the approach, but those are mostly about crimes committed by individuals, not corporations. When you're talking about HugeCo abusing customers, I think seriously punitive fines can work. But you need to make them painful enough that at least the board, and preferably the shareholders, want to ask questions about how exactly they know this won't happen again.
> I think the endgame from such a punishment regime is companies will reorganize their corporate structure to section everything off from such liabilities.
Of course they will. Any time a corporate entity can construct legal structures to capture more, shed externalities or shift risk, it will. Why wouldn't it? "We have a legal obligation to maximize profit..."
But that's not the "endgame of such a regime", that's normal business.
Deterrence is the goal.
On the other hand, a corporation rarely if ever does anything for reasons other than "revenue > costs"; in fact, it usually employs people making sure that ideas violating that rule don't get executed. So calculating a punishment in a way that erases all profits from the infraction and then some is a very good strategy when dealing with big companies.
If you’re basing the punishment on profits from the infraction, you still have to take into account the percentage of those infractions that are punished. If the fine is 5x what the company would make from that behavior, but there’s only a 5% chance they get caught, they may very well choose to do it anyway.
Also, corporations are made of people. An emotional punishment may sway someone high up at the company who has the power to reform it.
Companies will keep doing illegal things if they can make money doing so.