TL;DR: What are options for a Prince to punish undead rule breakers and which of these could lead to interesting subplots or character development on the side of the rule breaker?

So, there is this city, a few million inhabitants, melting pot for both mortals and supernaturals, and you are a somewhat anarchy Prince trying to keep order and freedom in an unstable balance. The primogen is, miraculously, behind you (you went through a lot together) and everyone plays their role in maintaining that balance. Behave like a sensible person and you can live your unlife in peace and freedom. Theoretically, it's the traditions. Practically, it's "do what you want, as long as you don't cause us trouble".

Now, you are a gentle spirit and value personal freedom very highly. But rather sooner than later, somebody does what they want and causes you trouble. Pesky neonates start a fight in the Elysium, a newcomer leaves bodies in the Ventrues' domain, the local undead starlet could not care less about the Masquerade, some monster killed all of the friendly neighbourhood Nosferatu's childer because they, well, looked like goblins or something.

Somebody has to be punished, and everyone is looking at you.

As a Prince, you have total control over what happens to the perpetrator (assume they have been caught and secured). What are your options? And, to make it more interesting, try to find options that could, in a meta sort of way, be a fun opportunity for the punished to have some character development or enjoy a subplot (because, of course, it is the PCs who cause all the trouble).

Here are some ideas to get you started.

• Final Death. Too final for most deeds, at least by your ethics. Also bad for PCs.
• Exile. Works, but needs to be maintained for potentially forever and your city is complex to begin with. Might also derail the plot.
• Stake 'em, drain 'em, hold 'em. Imprisonment for the undead. Good idea, unless time is critical concerning plot, which it is, at the moment, sorry.
• Torture. Again, ethics (you are not sacrificing your Humanity for that perp), as well as the fact that your impenitent victim might become an enemy over the years.
• Blood Bond. If it's good enough for Clan Tremere ... this might actually work out alright, given they don't realise the next Sabbat city is only a few miles away and turn on you completely to actually get the "freedom" you promised.
• Delegate the matter to your Sheriff, or the injured party. Great, that takes you out of the picture as Prince but the GM will still have to come with something. Also, you actually do feel it is your job as the one who "makes" the rules to adminster (and execute) justice.
• Make them fix their mistake. This could be great in some cases, but realistically, you'd rather have your trusty Scourge patch up the Masquerade before sending some neonates to make it worse - and whatever are they going to do about the dead goblins?

What are meaningful ways to punish a PC for their crime that could turn out to be opportunities for the player?

TL;DR: What are options for a Prince to punish undead rule breakers and which of these could lead to interesting subplots or character development on the side of the rule breaker?

So, there is this city, a few million inhabitants, melting pot for both mortals and supernaturals, and you are a somewhat anarchy Prince trying to keep order and freedom in an unstable balance. The primogen is, miraculously, behind you (you went through a lot together) and everyone plays their role in maintaining that balance. Behave like a sensible person and you can live your unlife in peace and freedom. Theoretically, it's the traditions. Practically, it's "do what you want, as long as you don't cause us trouble".

Now, you are a gentle spirit and value personal freedom very highly. But rather sooner than later, somebody does what they want and causes you trouble. Pesky neonates start a fight in the Elysium, a newcomer leaves bodies in the Ventrues' domain, the local undead starlet could not care less about the Masquerade, some monster killed all of the friendly neighbourhood Nosferatu's childer because they, well, looked like goblins or something.

Somebody has to be punished, and everyone is looking at you.

As a Prince, you have total control over what happens to the perpetrator (assume they have been caught and secured). What are your options? And, to make it more interesting, try to find options that could, in a meta sort of way, be a fun opportunity for the punished to have some character development or enjoy a subplot (because, of course, it is the PCs who cause all the trouble).

Here are some ideas to get you started.

• Final Death. Too final for most deeds, at least by your ethics. Also bad for PCs.
• Exile. Works, but needs to be maintained for potentially forever and your city is complex to begin with. Might also derail the plot.
• Stake 'em, drain 'em, hold 'em. Imprisonment for the undead. Good idea, unless time is critical concerning plot, which it is, at the moment, sorry.
• Torture. Again, ethics (you are not sacrificing your Humanity for that perp), as well as the fact that your impenitent victim might become an enemy over the years.
• Blood Bond. If it's good enough for Clan Tremere ... this might actually work out alright, given they don't realise the next Sabbat city is only a few miles away and turn on you completely to actually get the "freedom" you promised.
• Delegate the matter to your Sheriff, or the injured party. Great, that takes you out of the picture as Prince but the GM will still have to come with something. Also, you actually do feel it is your job as the one who "makes" the rules to administer (and execute) justice.
• Make them fix their mistake. This could be great in some cases, but realistically, you'd rather have your trusty Scourge patch up the Masquerade before sending some neonates to make it worse - and whatever are they going to do about the dead goblins?

What are meaningful ways to punish a PC for their crime that could turn out to be opportunities for the player?