The reason executives commonly avoid such penalties is because they avoid being found personally liable by claiming they didn't known, did misunderstood the situation, where deceived by others etc.
Through it should be noted that this case is a bit unusual and complicated. The tax dispute itself isn't as simple as Amazone directly having avoided paying their own taxes. And the case of missing taxes has already been settled. This new current investigations are criminal investigation (i.e. the failure of paying taxes is assumed to have been intentional instead of a booking error) and seem to be more targeting executives for having committed crimes (instead of targeting Amazone the company).
Or in other words, Italian prosecutors are feed up US companies not caring for EU law and no one being hold liable.
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(1): Without option to have it replaced with long time parole.
That’s ok for the big players with deep pockets. For the little guy this is a much bigger problem. As it should. It would just be nice if law breaking would be a bigger problem for the bigger companies too.
I misfiled stuff a few times and got fined, it's annoying but it's not something that will break your bank.
The behaviour of the tax office varies quite a lot from country to country tho.
But don't trust me, ask your lawyer.
New Zealand. The Accident Compensation Corporation, a compulsory insurance scheme, is absolutely feral. Will crush you "because rules" without a thought.
Each time I got a piece of mail asking my to call the IRS to clear it up, and every time the agent was nice and very helpful clearing it up, and not fined.
Businesses who get into trouble because of taxes are doing it intentionally. Or somebody in the company does it intentionally.