This is why regulation is rarely the answer. Corporate lawyers are ultimately more clever and better-paid than the congressional staffers that are writing the laws.
It's also much easier to find a loophole than it is to predict and avoid all loopholes, especially with all the compromise required to pass a law.
They don't have to be more clever. They just have to be faster to adapt, which is trivial given the glacial pace at which legislation is passed in the US.
They also have to make an example out of cases which they know they can win dead-to-rights. The chilling effect can be a societal good if used correctly.
Which also means that the regulatory agency most be structured to remain un-captured by the corporate interests it regulates, and empowered to react and adapt rapidly to the 'clever' legal hacks.
Correction: No lawyer is dumb enough to go on the record, or to leave a signature on something that could reasonably create the impression upon discovery that they knowingly want or facilitated the creation of, less safe commercial planes.
However, buying Boeing stock, with the current management in place, is synonymous with wanting less safe commercial planes.
This was glaringly obvious where I took a course on engineering law. So much boiled down to “don’t put bad stuff in writing” more than “don’t do bad stuff in the first place.” The press or made a point to distinguish the way engineers think can get them in legal trouble (eg, trying to be open and transparent about design flaws). It kinda bummed me out.
That's never the proposal but is often the outcome. Firing your engineers and outsourcing or eliminating large amounts of QA most would agree was likely to make Boeing planes less safe.
Yet no lawyer raised an objection. They lawyers also successfully argued that FAA testing was not needed and Boeing can and should be trusted to signoff internally.
It's also much easier to find a loophole than it is to predict and avoid all loopholes, especially with all the compromise required to pass a law.