Thought it might be interesting to give my thought on some parts ... Hope you don't mind.
Chekhov MacGuffin wrote:
Black Org Boss knowns and Speculation
Personality/Background
3) Uses alcoholic codenames.
4) The organization uses clever codenames, passwords, etc. based on mysteries and history. If the boss is behind the naming scheme then perhaps the boss has an interest in detectives and mysteries.
I wonder why they actually use alcoholic code names. It has no relation whatsoever to crows or Nanatsu no ko, and as you said in the fourth point, they usually use mystery or history codes. You could get away with a possible preference towards mystery and history from the boss, but I think it's too easy to just say he's interested in alcoholic beverages as well, and just decided to give them those code names. It looks too random in my eyes, like a kid would play around and randomly appoint some names to his/her followers. Besides, I have the impression the BO members get those names because their personality somehow correlates to the beverage.
Boss’s opinions/relations
1) Vermouth is the boss’s favorite so he/she allows her some independence and overlooks some of her potentially dangerous behavior. It’s confusing why Vermouth is the boss’s favorite when she actively engages in behavior which is encouraging the syndicate’s downfall - like protecting Conan and allowing Ai to escape. I have a hard time believing the boss could not see her traitorous intent. Obviously Vermouth has some characteristic that makes up for her actions. (The failure to age possibility?) At the same time the leader can also command the absolute respect of a wildcard like Gin who vocally despises traitors. Why would Gin follow a person who tolerates rogue agents like Vermouth? All of this makes me wonder what exactly makes Gin so loyal. Whatever the reason, the boss clearly knows people well enough to balance these contradictory personalities and their agendas successfully.
Don't forget nobody in the organization, aside from Vermouth and Kir, knows about Conan. I don't think they even know she let Haibara run free, since Calvados killed himself. And he was the only one alive 'till then who knew who Sherry was, except for Vermouth. Since the BO seems to STILL be looking for Sherry, not knowing she's shrunk, Vermouth certainly didn't tattle about her to the boss or anyone else (which is a feat, since she only promised Conan to give up on Sherry. Which means only SHE couldn't look for her, but she could still report about her to the boss).
So count that all together, and all the BO knows is the fact that Vermouth rampaged a bit, without any clear result. She made Vodka go to a halloween party (without any explanation apparently -> ch. 429 p. 11, and where a fake Kudou Shinichi appeared), was defeated by Akai, and denied any knowledge about Shinichi (in other words: she made Vodka go on that boat trip for no apparent reason at all, as far as Gin & Vodka know. And that fake Shinichi was purely 'coincidence'). She reported to the boss via sms, but apparently didn't say who Sherry was (otherwise Haibara would've been caught long ago). All the boss replied to her sms was that she'd gotten too much freedom. Makes me wonder, what DID she report about? A plan about her trying to get Akai on her own by using Jodie?
Anyway, what I wanted to say is: I don't think Gin sees her as a possible traitor. Not much to conclude that anyway from his point of view. Plus Gin is a very paranoid man and distrusts literally everyone, since he even threatened to kill his partner Vodka when he went to get a disk without telling Gin. (ch. 383 p. 9-10) And even if Gin noticed Vermouth's traitorous inclinations, every good organization is ought to have such members, the important thing is to keep them in check so they never give in to those inclinations. And as far as the BO knows, Vermouth never did, they probably don't even know that she wants to have them destroyed. It would probably come as a huge surprise to them, seeing as Vermouth does excellent work (information gathering about Kir's whereabouts, her assassination of Jodie's parents, ...) aside from her little so-called "secrets".
Stuff about the Black Org in General
Black Org’s goal
I’m favoring the idea that immortality or anti-aging is one of the ultimate goals of the organization.
"We can be both God and Devil since we are trying to raise the dead against the stream of time" Vermouth (380.13)
I don't really understand how that quote and the immortality/anti-aging theory are connected. I'm afraid I missed the explanation somewhere. What's confusing me is the fact that you have to see the quote as one entirety, and it seems to me everyone is focusing too much on either the "raising the dead" part (= immortality) or the "against the stream of time" part (= anti-aging). Even though I don't really call raising dead people being immortal (more zombie-like, heh). And even though I don't have a decent explanation for it myself. :P But maybe that's because it's ridiculously late over here already, because I remember thinking about it once and having created some theory, but I can't remember anymore what it was at all.
Well, I'll continue this another time, otherwise I won't have to go to bed at all. And I'd like to have slept a bit.
Ah, there's also a part about Asaga's (girl)friend further down, since that one was one of the most intriguing things on my mind. ^_^
/edit: change of plans. I'm currently experiencing the biggest disadvantages of living in a dorm. Everyone went out and came back bit by bit with a lot of noise during the night, and after that my neighbour decided to invite her boyfriend to sleep over and now they're merrily watching some idiotic series on the computer with the sound turned on. Next time I see her, I'll hyping kill her veeeeeeeeeeeeeeeeeery slowly by inviting her to the zoo and throwing her in the cage of the bears. I hear bears start with your extremities, so that should be a slow and painful death, enough to satisfy me.
Plus my computer is having issues as well. I really need to clear the dust out of it.
Anyway, let's get on with it.
Individual characters
Info and speculation on Vermouth/Chris Vineyard
This behavior is definitely not like normal black org behavior. She could be held “hostageâ€