A man sat at a bar in Esgaroth, a shot glass of whiskey on the counter before him. From behind there is little to see but a black hooded cloak and a head of brown hair worn in a short ponytail, but these belong to the man known only as The Highroller, second-in-command of the Guild of which this bar was one of the secret hideouts for. If observed for a time, his behavior would make it seem as though he is waiting on someone, which he was.
A second figure clad in a black robe enters the tavern, wearing a mask over most of their face. The robe was large, and when combined with the mask, even concealed any semblance of gender. Their head was down, but if you looked into the hood, all you could see was a mask and long black hair, which may make one presume that this was a woman; correctly, in fact, but that was not the whole story. For this woman was The Raven, the legendary spymaster of the Guild, and while some whispered her name at night, none knew who she truly was. She took a seat in front of the Highroller, and he got a better look at her mask. It appeared to be shaped like the skull of a bird, the beak curved down covering the mouth, and yet, there was a hole for the woman to speak, eat, and drink through. The eyes of the mask were deep, and through them, you could barely make out bright blue eyes, like pinpricks of frost hiding among the shadows. In the poor light, it was hard to make out any details about The Raven, and it almost seemed as if her figure itself was blurred, blending into the background.
"So, Highroller. You wished to see me?" She said in a charismatic and commanding tone, giving the man an unnerving stare.
"Raven." A curt greeting from the Highroller, but not rude. "I thought you were the intelligence master. If you cannot guess why I have called you here, then perhaps we should look into finding a replacement."
"If it was not clear, the whole bar needn't know of our purpose. In their eyes, we are just two..." A short pause, making it unclear if the masked woman was thinking, or if she simply desired to create an effect. "old friends. And they wouldn't be wrong. Isn't that right, young one?"
She opened her cloak, and a strong odor of flowers overwhelmed the area. The aroma was almost enough to make one cough and tear up, as if it was a deliberate weapon, or a hint of one. As she opened the cloak, the other hand reached inside, momentarily feeling something that appeared rough, bumped, and didn't shine whatsoever. It was hard to make out what it was. She pulled out a few papers, and handed them to the man underneath the counter. The papers carried the same scent that bombarded the senses of all nearby, although not quite as strongly as the woman did. It seemed they had simply been keeping them in there just a little too long. "So... what do you think? A carriage to Rohan carrying a shipment of arms and gold. A trading caravan to the dwarves. And the shifts of every guard in Dale" She almost whispered, her voice smooth and flowing like honey, sounding not quite natural, but as if she had extensively trained it to be that way.
The Highroller took the papers from the woman, beginning to scan them with his eyes. He paused for a moment, looking at The Raven. "Speaking of keeping our purpose to ourselves, you’re not exactly doing a great job of that. Besides, do you really think anyone in here tonight was allowed in without my express permission?" He takes a few more seconds to finish scanning the papers, holding a hand up to keep the Raven from speaking until he finished. "Very good work. So good that I'll let that 'young one' comment slide... for now." He chuckled dryly and waved to the bartender, ordering a shot of whiskey for the Raven, who took and downed it remarkably quickly, seeming to not be bothered by it.
"I've always liked strong liquor, you know. I'll have another one. A whole glass this time" she said as she put a few coins down on the table to pay. "And really... The young one comment... Do you even know how old I am? You have good potential. But brute force and knives can't get you everywhere in life. Sometimes, you have to look your enemy in the face and talk to them like they're your best friend to be able to defeat them" She chuckled a bit, downing the glass of whiskey just as quickly as the first shot.
The Highroller turned away from The Raven before he pulled off his mask to down his shot. When he turned back, his mask was back on his face. "When you face an opponent, give them time to learn about you, that's when you get hurt the worst." He reached up to run his fingers over his scar. "Strike first, never let them get the chance to hurt you. I'll agree that there are times that a brute force approach is... ineffective. However, speaking to someone you want dead is never a wise idea."
The Raven chuckled, an unnerving sound, and coupled with the perfume, it sent involuntary shivers down the Highroller’s spine. "Who says you have to tell the truth? I wear this mask for a reason. When you are someone like me, you have to, and do, take every precaution against every possible danger. Even if you need someone dead, if their guard comes down before yours, you have won. If you make them trust you, if you befriend them, they will never suspect your betrayal. They will tell you things you need to know, accidentally give you openings, and before they know it, they wake up with a slit throat, never even knowing why." The Raven paused, tapping her fingers on the table a bit, muffled slightly by fine black cloth gloves. "I know you may take some... satisfaction from personally executing your foes, but I need no such pleasure. It is far more entertaining to simply be the one pulling the strings. If someone needs killing, I have people for it. Being the one at the scene only leads to a greater possibility of being caught. And I take no such risks.”
The Highroller gave a dry chuckle. "That's why I never act directly against someone we want to die quietly. I only go in when we need to send a message. I'm sure you heard about the tragic death of that ship captain? The one who died from eating some bad fish?"
The Raven looked at the Highroller, and a little gleam of what may have been pride was visible in her eyes. "That must be an excellent story. You did well with that one. You have great potential, you know. You just need to work on it for... a few more decades. Then you'll be closer to a master. It's a shame that you never really live that long, you know." The sheen left her eyes, and they glazed over a bit before she quickly looked forward again. "Just do your best, and you will die without regrets." she says almost coldly, as if put off, which earned a chuckle from the Highroller.
"I'd die without regrets anyway. We can't afford regrets in our line of work, and I'd take every life I've ever taken again if I had to."
The Raven brightened up a bit again. "Excellent. That is as it should be. Without regrets, you are more willing to do what you must, and have less to hold you back."
The Highroller smiled at The Raven, but his mask hid the gesture. "I'm glad to see we agree on something. I knew there was a reason the boss kept you where you are. Keep up the good work, and I'll be in touch through the dead-drops to request the next intel packet." With that, he abruptly stood up and walked out the door, followed by two men, likely his goons, who had been sitting nearby the exit.
