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EDIT: I had no idea how long this was going to be when I begun writing it. I apologize if the length is obnoxious.
For those of you who haven't read the first volume of Hell's Vengeance, The Hellfire Compact, Cimri Staelish is a cruel, vicious, and manipulative young rogue who initiates the adventure's plot by convincing our would-be villains to partake in a tannery heist on behalf of her mysterious benefactor. Left to her own devices by her alcoholic parents, Cimri has had a rough life in her hometown of Longacre and mostly raised herself. She has acquired a number of different skills and makes her living as a local thief, thug, and smuggler. Cimri wields a kukri as her primary weapon in addition to her sap and daggers, but her main role in Hell's Vengeance is to facilitate the party coming together and to serve as their guide around Longacre.
However, I see a different role for this Neutral Evil cretin. Her backstory mentions her yearning to leave Longacre in seek of adventure and riches but not being able to commit for fear of ending up in a rut or biting off more than she can chew. What if she chose to travel to Kintargo? Cimri may wish to make a name for herself by serving House Thrune and helping crush the rebellious Silver City under the empire's heel.
This scenario assumes that Cimri has moved to Kintargo and enlisted with the infamous Chelish Citizen's Group. Her superiors recognize her talent and assign her to either leadership over a small squad or with low-level suppression, spying, and subterfuge operations.
Cimri would make an appearance early on, showing up at the protest in Aria Park that begins the adventure. Not being a native to Kintargo, few if any recognize her and those that do are unaware of her intentions. Seeing as how the protest is described as materializing slowly and drags on for several hours, it seems plausible to me that Cimri could be informed of the demonstration, briefed on the situation, given her orders and sent out to disrupt it within a reasonable timeframe.
Staelish is here as an agent provocateur to help undermine and break up the protest, possibly identifying insurgents and dissidents in the process. She can attempt to accomplish this in many ways. Here are a few of them:
A) Cimri identifies herself as a member of the Kintargan Libertine Movement and hands out parchment flyers to attending protestors. An opposed Sense Motive check against her +7 Bluff determines that her propaganda, slogans, and announcements sound rehearsed and insincere, but if called on this she simply claims that she is not a great public speaker and that she learned her slogans through rote memorization. The PCs can roll a Knowledge (Local) check to learn more about the Libertines. A result of 10 reveals that it is a small, radical Kintargan nationalist political movement calling for independence from House Thrune. A result of 15 reveals that the group has a reputation for fiery, radical rhetoric but has produced few meaningful results and that many of their members have been arrested and jailed by the authorities. A result of 20 or higher reveals that there are somewhat credible conspiracy theories that the group is in fact a "false flag" organization managed covertly by House Thrune and that it's true purpose is to lure rebels or would-be opponents of Thrune into captivity. If called out on any of this information, Cimri denies such rumors and accuses the PCs of peddling "Anti-Libertine propaganda".
B) Cimri's main reason for being at the protest is to incite violence and help weed out enemies of Barzillai Thrune. Perhaps, when the angry protestors toss manure at Barzillai Thrune after his spiteful announcement, he does not actually order Nox to "..run them off, arrest them, or kill them. I don’t care which!". The fact that Nox and her guards don't immediately advance upon receiving these orders always confused me anyway. Instead, Barzillai simply sneers and recedes back into the opera house, shutting the doors behind him. But not before he issues a sending spell to Cimri, issuing her the order to throw the dagger that, as written, wounds Nox and causes her to retreat into the opera house. Seeing as how Cimri's statblock contains a dagger as her ranged weapon option, this seems highly plausible.
In any case, her dagger toss serves as the signal for the Chelish Citizen's Group thugs in the crowd to reveal their weapons and begin attacking the protestors; triggering the first combat of the entire campaign. At this point, Cimri can take several different actions.
* She may simply flee the protest, her work having been done. The fact that none of the Dottari guards or Citizen's militia pursue her may seem immediately suspicious, but the PCs have a full-scale brawl with Thrune's minions on their hands and might not prioritize chasing her. Ideally, they won't. Emphasize the violence being inflicted on the protestors by the Thrune militia if you want to dissuade them.
If they choose to do so, prepare or improvise a chase scene using Paizo's chase mechanics as she weaves through the streets of Kintargo to avoid them. If cornered, she protests her innocence with a Bluff check. If the PCs can see through her lies and are unwilling to let her escape, she draws her Kukri and fights back.
To even the odds, she may attempt to seek out a Citizen's Group, Dottari, or Redator patrol and hold up her bronze Thrune pendant (which every Citizen's Group member possesses as per their stat-block), shooting out a finger at the PCs and yelling for them to destroy these "rebellious vermin". Roll a percentage dice with your desired parameters to see if she's lucky enough to find help.
* Cimri could instead remain at the protest and observe the fight between the PCs and Thrune forces, maybe partaking half-heartedly against them with non-lethal sap attacks to lend the impression that she is on the PC's side. If her inflicting non-lethal damage on the guards as they try to attack the PCs seems counter-intuitive to you, roll her attacks behind the screen and simply claim that she is missing repeatedly. Or perhaps the PCs may roll a Sense Motive check to notice her deliberate incompetence.
When Nox re-emerges from the opera house with her pet Hellhound in tow, Cimri follows the party's lead as they presumably flee the park. She stays with the party for as long as she deems necessary to gather information about them and report back to her superiors. Cimri participates or observes as the party battles Citizen's Group militia in order to save Rexus Victocora, and accompanies them to Crissali's Fine Tomes.
She might ask for their names or other information on them, under the guise of making an alliance or befriending the PCs. Before too long, Cimri tells the group that she must "Report back to her Libertine comrades" and plan for the oncoming rebellion. In actuality, she intends to report back to Barzillai, telling him the PC's names, likenesses, and any other relevant information.
Her deception can take numerous forms. Cimri might try to retrieve hair samples to enable scrying, inform them of an upcoming "underground Libertine meeting" that is actually an ambush, give them a "useful" item that has an Arcane Mark upon it, and other wicked plots. If she is informed of the PC's intentions to visit the Livery, they may find a squad of Dottari waiting their to greet them (possibly struggling with the strange, poltergeist-like phenomena inside), or they could blockade the exit as the PCs attempt to leave. At your discretion, she may try to prolong her infiltration of the party even further, accompanying them to the Long Roads Coffeehouse and Wasp's Nest. At this point, Cimri's ability to breach the PC's "operational security" is an existential threat and they may find the campaign coming to an early end as Nox Dimension Doors into their hideout to snuff out the rebellion before it can even begin.
In all likelihood, the chances of Cimri being successful to that extent are very remote. At +7, her Bluff is not so high as to be impervious and it is highly likely that the PCs will be able to see through her deceptions quickly. Give the PCs several opportunities to roll Sense Motive checks as she attempts to appear benign or helpful, the first being her rhetoric at the protest, the second being her behavior towards the Thrune units (and vice-versa), the third being her effort to secure the party's allegiance, and so on. Eventually, the PCs will see through her fog and mirrors and lose their patience with her.
When Cimri's true colors are revealed, she may attempt one last Bluff check or could simply attempt to flee. If she is unable to do so, she curses the PCs while drawing her Kukri and making a last stand. Hopefully, having the party gang up on the slimy, lying, disgraceful rogue and cutting down the fool right where she stands should prove amusing.
C) Or maybe she doesn't attempt any grand act of deception, instead serving as the squad leader of the Citizen's Group thugs that face the PCs when the protest turns into a riot. With AC 16 and 13 health points, the NE Rogue 1/Warrior 1 will last a little bit longer than the average thug and provide a tiny bit more challenge, being the first named minion of Barzillai the PCs kill.
In any of these cases, if Cimri escapes her first encounter with the PCs she stays in Kintargo and continues serving Barzillai's regime. She leads a gang of four to six Citizen's Group militia and could run into the heroes once again while on patrol, overseeing a doghousing, or engaging in some act of thuggery like looting the houses of accused rebel supporters. When she sees the party again, Cimri yells "You again! I won't be so easy on you this time, rebel maggots!" and engages them with her comrades.
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Lots of really good ideas!
Thanks!
I was supposed to be writing an essay when this idea popped into my head, so I ended up writing this essay instead. I tried to think of each possibility and outcome. I don't think this is a concept that would interest a lot of people; but if just one person integrates any of these ideas into their game than it wasn't wasted.
I like the idea of trying to redeem her, personally... but then, I like a challenge.
Nice write-up, thanks. Think I'll use this, I especially like the double-agent angle. I also like the idea that there's other rebel groups in Kintargo apart from the Silver Ravens (even though Cimri's group is a false flag one). I always try to convey, if possible, that there's a living, breathing world outside the doors of whatever inn the PC's are holed up in - regardless what the PC's do or don't do the wheels will keep turning.
I also think I'll cook up some more rebel gangs, thanks for the inspiration. Like a real hard-line one and a softer alternative. Maybe even a The People's Front of Judea schtick. Splitters! :)