I'll handle Trinia and Pagrip's obstacles in reverse order now, as she's got initiative dominance now.
1d12 ⇒ 4 hidden shortcut, perception DC 15
1d12 ⇒ 6 narrow rooftop leap, acrobatics jump DC 15
Trinia slips out from under Pagrip's grasp and rushes off, leaping across to the next roof without breaking a sweat, then she suddenly changes angles and rushes towards the far side of the building. Roll skipped, auto-success
1d12 ⇒ 8 tightrope shortcut, acrobatics balance DC 20
1d12 ⇒ 12 wide rooftop leap, acrobatics jump DC 25
Pagrip sees Trinia's sudden change in direction and thinks he spots a way to head her off along an aging rope that stretches across; or possibly along an unlikely jump further along the roof.
Should Pagrip catch up with Trinia, he gets another grapple attempt.
Remember you can use your tarot cards for Dex-check re-rolls too. In fact, you can even re-roll your re-rolls with extra cards.
"Have you ever seen a dwarf tightrope walker? With a little more flare I am sure we could raise some money for the church with that little performance. Ooh. Um. You think we could make it under the dwarf to catch him? Maybe I could throw Reginald to break his fall." she says almost sarcastically.
To Trinia, Esme shouts "Catch you later!" and waves.
"How can you be so flippant, Darkbane?" Caulder snaps, rounding on her savagely. "We just failed our mission. I told those citizens that the authorities were taking the suspect into custody so they didn't have to take matters into their own hands, and now I've lied to the people! If that were Lamm escaping again, would you be laughing? Or do you only exercise yourself enough to give a damn about crimes that directly affect yourself?"
Just a side note regarding Harrow deck use: you still a ways from the end of part 1 - but the Harrow uses expire then; replaced with new Harrow uses and new options.
Pagrip finds himself on the middle of the tightrope, trying to keep steady - but the rope has begun swinging quite wildly back and forth as the dwarf tries to keep his balance shifted in the right way.
Further ahead Trinia is about to leap down from the edge of the roof; when suddenly she turns around and tries to sprint backward. Her eyes are wide in shock, which is explained moments later when a squadron of Sable Company marines riding on hippogriffs rise from below the edge that Trinia had wanted to use. It is a matter of moments before they catch-up to Trinia and have her arrested. The girl wails her innocence, while a general cheer from the streets below erupts at the proceedings.
Pagrip is still on the tightrope, he can complete the crossing forward or back at the same DC, or risks falling when failing by 5 or more.
"That's hardly fair, Cleric. This is nothing like Lamm. We all knew he was guilty. We have only hear-say that Trinia is even related to the crime. Don't use others as a release for your impotent rage!"
Esme gestures at the hippogriff riders.
"See? You didn't lie. An authority has taken her into custody. It just wasn't us. And at least we know where to find her now."
Pagrip teeters in the middle of the clothesline, worried that it will snap at any moment. He sees the Sable Company marines swoop in and take Trinia away, and he sighs. "You have got to be kidding me," he grumbles, and turns around to start making his way back. The clothesline holds and he bounds back onto solid ground. "We risk life and limb jumping through the Shingles and the bloody Sable Company could have done that the whole time?" He begins making his way back to the others.
"I don't care if she's guilty or not," Caulder snaps back at the paladin. "And you shouldn't either, Darkbane. We were ordered to bring her in; our personal opinions on who is or isn't guilty are irrelevant." He scowls after the Sable Company. "Looks like we were just the patsies to chase her out of hiding anyway. Should have known they wouldn't consider a crew half composed of civilian vigilantes qualified to handle a real high-profile case. I don't mind being the distraction, but I'd appreciate being let in on the plan. C'mon, Darkbane. We have to report back to the Field Marshal."
"Of course it matters. We are not unfeeling Hellknights. While it was our orders to bring her in, I don't feel particularly bad for failing to do so. Sable Company are allies of the city, last time I checked. And Trinia wasn't ripped apart by the mob. A good result, all told."
As the hippogriffs depart in direction of the palace the four make their way back to the Field Marshall. It doesn't take long, a prior appointment is ushered out of her office and she receives them quickly. Her face looks a bit grim and pained at hearing that the marines caught Trinia. "That is... unfortunate. I would have preferred to control the interrogation of the suspect. As is, the Sable Company has been commandeered under the direct order of the queen during martial law - and this state has not been lifted off the city yet." She sighs.
Sense Motive, DC 14:
Unspoken in the air is her concern that Trinia will not receive a fair hearing by the queen herself.
"Can't get them all. Please look after yourselves. The streets are not entirely safe tonight - with the remnants of the mobs still about." With that she dismisses the party.
Unless the PCs wish to raise some concerns with her :)
There is a long pause, before Cressida responds, "In better times certainly. The queen has prepared her interrogators and they are with Trinia first - irrespective of their findings, their verdicts are beyond contestation. Our hope was that we could get hold of her first."
"No, thank you for your efforts." The Field Marshall is about to dismiss the four when an out-of-breath runner raps on the doorframe to the office, then at Cressida's nod he enters and delivers a document "from the palace".
Cressida studies it quickly, her eyes scanning the lines with the practiced ease of those who are regularly exposed to legalese. She pales a little and shakes her head, almost imperceptibly. "They not wasting time, this is a proclamation that Trinia's been arrested and has confessed to the murder of the king. She'll be publicly hanged the day after tomorrow, at noon. Perhaps you owe it to her, to see her off. Thank you again, I hope for more success next time. Please see yourselves out."
Esme briskly walks out of Cressida's office with a grim expression " I'm going to speak with the Sable Company and maybe the Queen. The rest of you may accompany me, if you wish. I am sure you have better things to do with your time."
It's not your place, Darkbane," Caulder tells her sharply. "What are you going to do, march up to the Queen and tell her" (he affects a high voice) "'I'm a foot soldier from the lower echelons of the Bank of Abadar and not even here on their authority, but I think I'm more qualified to conduct an interrogation than your trained professionals?'" Returning to his normal timbre, he goes on, "Getting this over with quickly is the smartest thing they can do. She's demonstrated she's slippery; the longer they try to hold her, the more chance she has to escape, and then the city will really explode. We're already at a point where the agencies of the law, from the Sable Company to the Hellknights to the city guard, are starting to distrust and work against each other rather than together for the good of Korvosa. Be a smart girl, and let it lie, for the sake of the citizenry."
Pagrip shakes his head sadly when he hears the news. His eyes narrow at Caulder's words and he looks about to say something angrily, but he pauses, takes a deep breath, and says calmly, "You're right, Caulder. They've played this very well. Whether the girl is guilty or innocent, the people believe she's guilty, and they'll explode if she gets released or escapes. It doesn't change the fact, though, that was way too quick a verdict for a fair trial. Even if she is guilty, which she might be, justice has not been done this day."
He sighs. "I, for one, intend to be there at her execution. Not to revel in it like most will, but... I don't know what good it'll do as she won't likely see my presence as comforting, but I did promise her I'd do my best for her, and I don't know what else to do. Except get a drink. Who's with me?"
The following day proves to be one with rising expectations. Word of Trinia's capture and pending execution have spread like a wildfire. Korvosa is in a state of restless excitement: life goes on, but things are a bit directionless and agitated. As Field Marshall Cressida would note, the violence and lawlessness ceased. At least for now.
Esme eyes narrow as she looks at Caulder. "At least I am going to try." And she storms off.
Esme will attempt to try to see the prisoner for the rest of the day and well into the night generally making a nuisance of herself until either she gets to see the prisoner or the execution day arrives.
Diplomacy 1d20 + 8 ⇒ (12) + 8 = 20 for what its worth
Despite her best efforts, Esmerelda is turned down at the palace whenever she raises the desire to see the prisoner. She is told that the prisoner - guilty of high treason and regicide - is under maximum security and nobody is allowed to see her without appropriate clearance.
The day of the execution arrives ever so swiftly, and before long the sun is reaching for the peak of the day. Eodred's Plaza is filling up. In the course of the morning carpenters have swiftly erected a hangman's platform - easily 30 ft square - and even before the condemned arrives a contingent of hellknights surround the platform, halberds at the ready.
The crowd that has been drawn to this event is sizable, perhaps one in twenty in Korvosa is attending; making it a count of roughly a thousand. The presence of the hellknights and their aura of menace keeps the people relatively at bay.
Esme also makes her way to the front, standing a little closer than the crowds and giving those around her a little relief from the hellknights menacing aura. If she spots Pagrip she moves to stand near him.
I guess Caulder would be wherever the Bank sends him, whether that be looking out for the businesses on his usual beat in case burglars take advantage of the excitement elsewhere in the city to strike, or providing extra crowd control at the execution, although his Perception score makes him spectacularly unsuited for watching for pickpockets. He does have a day job, after all.
The crowd has swollen thick, an excited buzz is in the air - there is even a certain sense of relief, as if the city itself feels like it is about to close a chapter in its history.
A short squat man, dressed in subdued yet pompous clothes steps onto the stage of the hanging with the air of a man who knows his words will hold the crowd's ear. An expectant hush descends on the plaza as he makes to speak. He produces a rolled parchment which he ceremoniously unfurls and presents triumphantly to the masses.
"Hear ye all gathered! This day marks the execution by the rope of Trinia Sabor. Guilty of attempting to seduce a man in wed-lock, murder, and high treason to the crown of Korvosa! The words on here" - he holds up the parchment - "are the confession of the traitor herself who has admitted to her heinous acts!" The crowd angrily boos at crimes, but cheer as the man continuous: "Only by the bravery and self-less sacrifice of the Sable Company marines could this dangerous villainess be caught before her plots could sink Korvosa deeper into madness!"
Ten does not manage to spot the dwarf among the crowd - it is too busy a mass to easily find somebody that doesn't stand out heavily in a crowd.
Caulder's received instructions by the Bank who want a senior cleric experienced with the street present at the execution. Abadar's teachings highlight the potential risks at gatherings - and having a man of the cloth at hand to keep a cool head is protocol.
Chance does allow for Pagrip and Esmerelda to find each other in the crowd. Almost center-stage. The imposing and authoritative presence of the paladin ensures that her spot is uncontested by the throngs, and Pagrip benefits from this by association.
"Take a look at the face of a traitor!" The crier points to where a guard of four hellknights hold four chains that end in an iron collar around Trinia's neck. With brisk step Trinia is moved to the platform - she can barely keep up. Her eyes look haunted and sleepless, her body looks frail and smudged.
Perception DC 10:
It is apparent that Trinia's body deteriorated significantly in the last two days. Terrible things must have been done to her.
Sense Motive DC 15:
There's a barren look in her eyes that cannot be purely exhaustion and resignation. Possibly some other means have increased her compliance - whether that is torture, drugs or magic... who can say?
"Would it be a horrible thing to say that if she had gone with us quietly, she would not have been horribly tortured and put to the noose? I think it would be a horrible thing to say. Forget I said it." Esme mumbles to herself.
Pagrip fidgets uncomfortably, and stares forlornly at the execution stage. "Not nearly as horrible as what's about to happen," he responds to Esmerelda without looking away from the stage. "Honestly, I'm tempted to make a futile rescue attempt. It would just end in utter failure with me dead, along with Trinia and possibly a bunch of other people injured in the process, so there's no point. But the temptation's there."
Suddenly several thunderous bangs explode, along with several plumes of smoke that rise on or near the platform! In panic the crowd's shouts drown out rational actions and several pushes and shoves edge the crowd forward - to which the hellknights respond by brandishing their weapons right at the panicking crowd.
...just before things can get fully out of hand the smoke plumes clear - and on the stage stands a black-clad man. His hooded countenance reveals nothing, but his stance suggests a man incredibly comfortable with weapons and the graceful imbedding of them in his foes. Almost at once the mood in the crowd changes, almost in awe whispers flow to and fro, Blackjack! It's Blackjack!
When he speaks all present fall silent, his words echo in the minds and hearts of those who hear them: "No justice is in this execution! No peace can it bring to Korvosa! The only traitor to our city is the murderous queen and her plot to ruin our pride, devastate our homes, and bury our children!"
Knowledge (arcana) or Spellcraft DC 15:
Magic could create the display of thunder and smoke - though it would take competent casters that are exceptionally well coordinated; or a very high level illusionist.
Craft (alchemy) DC 15:
The thunder and smoke are likely the coordinated use of thunderstones and smokesticks.
Knowledge (local) DC 5:
The figure known as Blackjack serves the poor and downtrodden of the city, fighting against the injustices of cold-hearted nobles and dark-souled merchants. Although he has not appeared in more than a decade, people have no doubt he still lives somewhere in the city, waiting for the next great travesty of justice for a chance to come forward and render aid. He's a hero to the common man.
Knowledge (history) DC 10 (only if you made the knowledge local check):
As much a legend and rumor as a known man, the black-clad Blackjack has remained a fixture of Korvosan lore for more than two centuries.
Because he has existed for more than 200 years, nobody in the city believes him to be a single person. The most popular rumor surrounding Blackjack places him as a series of human men, with one training the next down through history. Another popular rumor claims he is an elf, ghaele eladrin, or some other member of a long-lived or immortal race who exists in secret among the short-lived humans of the city.
Both Perception and Sense Motive DC 17:
There is something... familiar about the black-clad figure. Even though it's impossible to put the finger on exactly what. The stance, his mannerism, the way his presence beckons to the crowd... something...
Esmerelda draws her greatsword and shouts at the hellknights "Turn around you fools, you are pointing your weapons in the wrong direction! Arrest Blackjack the vigilante!" while pointing her blade at the person in black on the stage.
To Pagrip Esme mumbles "Blackjack looks vaguely familiar don't you think?"
The black-clad Blackjack is either oblivious to, or purposefully ignores, the crossbow bolt that had so narrowly missed him. His words don't incite the crowd into violence - but they definitely harken to his words and grow quite lively. Most of the hellknights have their hands full trying to keep the press of the people at bay.
Blackjack speaks: "The usurper queen is not of this city! Her allegiance is to Cheliax, she does not understand Korvosa nor has she a love for its people! Look! Look at innocent Trinia Sabor, an artist! Not a murderer! Will you have the whore queen slay an innocent as a scapegoat for her own treachery?" The masses begin chanting "No!"
"Oh great," Pagrip mutters, "you put on a black suit and suddenly everybody starts listening to you. He's probably not even the original Blackjack. Blackjack hasn't been seen in something like ten years. Anybody can put on a black suit." He continues mumbling, something about wishing he'd thought of it first.