Arrogance is not a trait isolated to a specific age group. The oldest wizard can be just as arrogant as the youngest warrior. There's no distinction between the two or some special characteristic that shields one in a cloak of wisdom. Only experience and humility can help with that, but there are just some people who never learn.
Of the two women I met in Vilpamolan the day of the kestrel theft, Shiloh was clearly the adult. Her irritation was understandable, but she managed it well. Brownie points were in her favor because of the fact that she decided not to attack me, and I admired her above average patience when compared to most other individuals who were both in her field and looked as young as she did.
'You'll make a good thief yet,' I thought while listening to her question about the singing. The detonation hadn't occurred just yet, so I was able to address her concern calmly. "You'll find out, soon enough. I recommend stuffing the kestrel into a pillow when the time comes, as that will mute it more than your sack." In truth, a pillow would be an effective countermeasure to the singing, especially one with above average stuffing inside. The pillow wouldn't completely mute the statuette, but any sound coming from it would be quiet enough that someone could transport it without notifying the entire district.
Whether I would have had time to explain that is all rather moot in hindsight, because the fire from earlier nicked some liquor barrels at that exact moment. Lightning ball and fireball spells – as I later discovered to have been used at the docks that day – are normally incapable of causing an explosion loud enough to be heard over long distances, let alone one powerful enough to destroy anything bigger than a skiff on their own. However, they can still start fires that are dangerous around highly flammable substances.
The person using the boats that had been torched by these spells had also been smuggling some high proof alcohol that day. As soon as the flames hit the barrels containing this merchandise, they ignited and shattered the boats into thousands of splinters. Pirates all over the district noticed that, as did Shiloh and I. Now everyone knew an intruder was running amok, and my masked acquaintance didn't appreciate that one bit.
I watched Ms. Kyrie as she harshly regarded Vinsue for her actions, not making any effort to stop their argument. I didn't blame her one bit for refusing partnership before running off. In fact, I probably would have done the same in her position.
After she left, though, I got my own taste of the trait I mentioned earlier. Vinsue, who introduced herself as Silvertail that day, proclaimed her reign of chaos was far from over. She made the ludicrous claim that she had freed nearly every slave in Vilpamolan by herself, when there were still several dozen, ongoing slave trades in the city that day. So confident in her own accomplishments was she that she couldn't appreciate how small her contribution had ultimately been. That was arrogance in its purest form.
If not even the kingdoms of the world or the deities could permanently purge Vilpamolan of slaves, this Silvertail certainly couldn't. Anyone that tried would already be marked for death by the slave traffickers that actually knew what they were doing. Not even purging the city would work toward that goal, because the slave owners would just find different ports to operate in. That is the sickness of man.
Yet because of my desire to remain uninvolved with this troublesome dragon, I didn't bother stating these facts just to point out her faulty reasoning. Exasperated, I just sighed, and gave her some brief chastisement before disappearing with the wind.
"Correction: you've freed most slaves from the novice owners you could find. This is Vilpamolan: the slavery capital of the world and not some pet project that a lone person – who doesn't even know the definition of subtlety – can fix. With your current tactics, you're likely to cause the deaths of more slaves than you save." With that, I vanished. Wind meld carried me across the rooftops faster than normal running ever could, all while invisibility covered my tracks. Eventually, I slipped into a mouse-sized hole in a nearby building, quickly finding myself in a room long abandoned.
The chamber had a wide view of the area, and was just close enough to my favored thief to allow me to help her without revealing my presence to anyone else. The door was barred by a rusted lock, while a skeleton hung from the rafters. He had likely been some poor bastard who owed too much money and decided to disappear, but the fact that he had been undisturbed for so long except by scavengers meant his resting place was perfectly safe to cast off my invisibility in.
It was there in that dust-filled chamber that I heard the infamous singing I had warned Shiloh about. The kestrel wailed out into the sky, drawing pirates toward it like in ages past, but I still wasn't fully committed to helping its newest owner escape from the homing call.
I had to make a decision in that moment. Would I help Shiloh escape or was it none of my business? Part of me wanted to capitalize on the theft: to paint several portraits of the thief and market it as a short story of a successful, romantic individual. Another part of me, however, also thought that Vinsue would make that act particularly difficult, and so wanted to drop the whole thing altogether. In the end, I couldn't decide on my own, so I let lady luck give me some help.
There was a dusty coin in the corner of my hideout along with a formerly luxurious pillow that had seen better days. I grabbed both, and flipped the coin while Vinsue was already shouting at Shiloh.
"Heads," I said, having not noticed that the coin I was tossing was actually a double-headed one. Of course, I saw that after I had already flipped it, but didn't feel like going to the trouble of finding a regular coin afterward just to redo the whole affair. Shiloh had won my help according to luck regardless of the circumstances, so I quickly went about communicating with her before any stray arrows decided they were hungry.
~No one wants a portrait of a dead thief, and luck's on your side today,~ I said to her telepathically while quickly summoning a sewing kit to work on the pillow I found. ~So I've decided to actually start helping you beyond idle chitchat. Ancestors know you need it, what with that Silvertail following you.~ By that point, Shiloh was already well aware of the dragon following her, so I was just being captain obvious with my statement. The cheekiness gave me time to fashion a primitive button pocket in the pillow for Shiloh to stuff the statue into and achieve some quiet. I immediately sent that to her via portal once it was finished, having it appear directly in front of her at chest level while another telepathic message sounded off. ~Use that pillow to close up the statue. It's old but has just enough stuffing to help.~