I see no reason to assume what someone was or was not thinking in this case. Both parties had sufficient resources to do due diligence, and both parties engaged completely voluntarily under zero duress.
My heuristic is that whenever someone insists on emphasizing that something iS NoT iLlEgAl, then they're probably trying to obscure that something is wrong.
Only if you view rules as pointless adversaries to be beaten. But often rules exist for good reasons to keep people safe and keep interactions fair and trustworthy.
Bending rules isn't something that you should take inherent pride in, and personally, it always lowers my opinion of such people.
Self dealing is very much breaking the rules. Sure, maybe the powers that be let it slide, but it is not playing fair.
Edit: in fact, when the musical chairs stopped and the IPO failed, there were lawsuits about the self dealing. So long as people were making money the board were willing to look the other way.
This is a lazy take on morality. Neumann enriched himself from wealthy, supposedly sophisticated investors. So sad. He took (not stole, took) from the rich (which they willingly handed over), gave to himself, and walks around free with no criminal prosecution to speak of.
We might disagree on what constitutes “bad people.”