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I'll use a specific example for this question, just in case a it helps and the question might be too general on its own:

If a vampire in Las Vegas were to try assert themselves and establish their own criminal enterprise, with control over things such as a decent chunk of the city's drug trade, smuggling and prostitution: would them just taking it upon themselves to take such a potentially powerful role be tolerated by the Camarilla there?

If the vampire actively and frequently aids high enough up Camarilla members and proves to be an valuable to them with their resources, I feel that might help their case in keeping others off their back in a "Can't Kill You Still Need You" way, but...that still feels questionable and very, very precarious.

Especially if they started being referred to by others as a "Crime Baron" or "Kingpin", whether by humans figuring there to be one in the city, or actual vampires familiar with the existence of their operation.

The Prince of Las Vegas, Benedic, is referred to as not too strict:

Being prince for over 50 years now, Benedic has a laissez-faire attitude towards his princedom

But, a vampire taking on such grand titles still feels like it would be a potentially severe insult to the vampires with actual ones in their society, such as that Prince.

And then there's how while the scheme is very typical Ventrue in behaviour, in the modern day, the Ventrue as a whole are actually quite co-ordinated with things like "the Board" and assessing and image concerns and all that: So, perhaps someone doing the above sort of grab without asking permission - due to factors like highly necessary sneakiness and a very short opportunity window to gain such a role in the criminal underworld- might be an issue?

Especially as it may seem unearned - or even like a threat - and make someone look bad

Am I right in thinking all of that, or is there no real rule against such behaviour as long as Kingpin maintains the Masquerade?

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What you're describing is the state of being autarkis, which is something the Camarilla has a word for at least. An autark is a vampire who's powerful enough to be a political force by themselves — too dangerous to try to confront directly but, unlike enemies like the Sabbat or some kind of draugr, not an existential threat to the sect as a whole. In cases like that, it might well behoove the Camarilla to make some kind of "arrangement" with them, allowing them leave to operate in exchange for money, boons, or some other kind of token.

The line worth crossing, I suppose, is if this vampire starts getting other vampires to swear allegiance. At that point, what you've got is a rival powerbase, which can't be allowed to stand. The Kingpin would have to swear fealty to the Tower and the local Prince or face the might of the Camarilla as a whole.

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If there's a reason for the Camarilla to tolerate a vampire who ( i assume ) is not affiliated to their sect formally, they will.

If you're having troubles providing legitimacy for his position, adding some intrigue in the form of a potential plot-hook is never a bad idea, as it gives power to your players, and they won't feel railroaded.

Maybe this individual is at the moment of the campaign becoming a problem and your players are tasked to keep an eye on him.

Perhaps he is acting as some form of contractor, providing a much needed service to a struggling Camarilla.

The world of darkness is well suited for deeply rooted schemes and intrigues, with the evergoing Jyhad thumping in the back of vampires minds, so don't be afraid to experiment with power schemes

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In the "Chicago By Night" book - Vampire 2nd Edition I think (maybe Revised) people such as Al Capone are listed - and we all know he ran his own criminal empire - My guess would be that much like Jadasc said in the first answer as long as the Primogen of the city , (and/or maybe its Prince) are getting a cut of said Vampires resources be it money,information or other "trade-able" wares - he might even enjoy the protection of some of the "higher ups" even if he is not a "official" member.

Of course such a alliance would not allow said Vampire to run amok, either - he/she would have to follow the code of conduct they lay down to the best of his abilities, a death here and there might be overlooked, while laying waste to city block might bring his allies to use the "plausible deniability" clause.

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I can't see any reason why camarilla should not tolerate kingpin.

From that what I remember, vampires follows own laws, not a mortal laws. So as long as he follows and obeys camarilla rules, he should be fine. Of course that what he is doing might cause some issues with other vampires, but it will be purely on personal basis.

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