The last time I looked which was a couple of years ago there was nothing in the ARIN TOS that said "you can only control one entity that applies for resources".
Joe Schmoe Enterprises, Inc, Joe Schmoe, LLC, Joe Shmoe Fishing Services, Inc are different legal entities even if Joe Schmoe, Jr owns all of them.
I presume the specific problem will have been when Joe Schmoe lied on the paperwork for IPv4 delegation to Joe Shmoe Fishing Services not mentioning that Joe Schmoe, LLC already has also applied, as has Joe Schmoe Enterprises, Inc. I'm not in ARIN's region, so I haven't seen their paperwork, but analogous paperwork in RIPE for example asks you about Related Entities because you're not entitled to duplicate resources just by asking more than once.
Except if you're a magician, of course!
The goal is to create a scenario in which the audience knows they were tricked but can't figure out how. So you don't lie and say this is a random audience member when it's actually an employee "stooge". But when you're giving the genuinely random audience member a "free choice" of cards you don't need to explicitly tell the audience that, duh, as a magician you're not giving anybody a truly "free choice" of anything actually and you knew immediately which card they picked even without seeing it. That sort of thing.
Are there grey areas? Sure. In particular there's a passive sort of deceit in which you let people assume things that you know aren't true, to your benefit. Mostly the law holds that it's their mistake for not asking, and anyway they'd usually be far too embarrassed to make a fuss if they realise their error.
I don't see that here, the plan was explicitly to trick the RIR into giving them resources they were otherwise not entitled to. Those resources were for everybody to share, they're stealing from you and it's appropriate to prosecute for fraud.