A long time ago I copied someone's list of theories from somewhere either in the DTCP or Holmes forum and then added on to it, so whoever you are out there who wrote the original I based this on, I'm sorry I forgot who you were, but I would like to give you credit so respond if it's you. I think part of this was originally Solera's, but I'm sure there are others too.
Later Edit: This is outdated. Please refer to
here for the most recent version.
Gosho's giveaways
From the extra Detective Conan book:
1. Aoyama had already put the name of the boss somewhere on the manga. (in some form or another I guess…) (I wish I knew when this quote was made whether in the book or in an interview so then we could narrow it down to chapters before a certain point)
2. Aoyama suggested that the true name of the syndicate, which has also never been revealed, is tied to the identity of its leader. If the Black Organization's real name were revealed, everyone would know who its leader is. This seems like a pretty big hint.
3. Aoyama also said that Ai would be really shocked if she discovered that that person is the boss." This is hearsay: someone wrote somewhere that this is what Aoyama said during an interview... (so the person does not trigger the black org sense)
What is it that would convince Ai that it's not "that person"? She obviously knows who this person is, if only she met or heard of that person once, otherwise I don't think it would shock her hearing about who it is. So I came up with 3 possibilities:
1) She trusts this person dearly.
2) The person wouldn’t fit Ai’s expectations
2.1) The person seems "useless" or of unsuitable personality to actually think of them as being a mastermind behind a large organization. This person would probably not trigger Ai’s “black org sense.”
2.2) The boss’s front job or status is unexpected (like the police force or a regular salary person rather than a company boss or political figure)
2.3) Boss is relative of someone close to Ai.
2.4) The person's age is unexpected. Given the aging wonkiness that has gone on we can’t rule out the possibility that the boss could even be a “child” somehow mucked up by drugs or whatnot which would explain why the boss only uses email to avoid allowing people to hear his youthful voice and avoids letting people meet him/her although this behavior can simply be explained as generic cautiousness.
3) She thinks this person is dead. Her parents would be an example of this, although why would they kill their own daughter?
Personality
1) Black org boss uses the song “Seven children/ Seven year old child” to encode his email. It is likely the Boss is probably Japanese, grew up in Japan, or had Japanese parents, relatives, or spouse as this is children’s song not well known elsewhere. Is this the reason for the Org’s black crow dress code? Do the contents of the song reveal something? Does the boss have children? Is a "child"?
2) Uses alcoholic codenames.
Boss’s opinions/relations
1) Vermouth is the boss’s favorite so he allows her some independence and overlooks some of her behavior. The leader can also control a wildcard like Gin pretty well, which makes me wonder what exactly makes Gin so loyal. Certainly not by blackmail (If that was the case it would seem like Gin's personality to hunt the boss down instead), possibly exorbitant amounts of money, but I favor a "debt" or promise of some sort, or other personal reason.
2) The Boss thought Akai Shuuichi could become the org’s silver bullet. (434)
Location
The infamous nanatsu no ko number has a Tottori area code. Gin and Vodka got off at Tottori when they left the train after the briefcase case (no pun intended). There were reports of quite a bit of organized crime in the Tottori area and somewhere in issue 46 Tottori came up again. In short, Tottori and the B.O. show up fairly often in connection to one another. We can't rule out Baker and Hyde cities of course as a good deal of the action takes place there too.
At the Pisco Hyde Hotel case, Gin was given the order to kill Pisco “in person.” (242.14) This info narrows down the location of the boss at that time to somewhere in driving distance of the hotel (forgot where the hotel was {was it Baker hotel?}). Furthermore Gin knew about the photograph implicating Pisco, but he may have learned about after giving the order (maybe from Vermouth at the party)
I can’t say for sure when the order was given. If it was when the boss realized there was an incriminating photograph that hadn’t yet come out in print, the boss had to be in the immediate vicinity of the hotel or at the party personally. If the boss gave the order sometime around when Ai accessed the computer, the boss is in driving distance. I cannot tell precisely the reason Gin was given the order. The order may have possibly been meant for another reason other than Pisco was caught on photograph. It could be because of the password attempts on the computer and the files accessed by Ai raised some flags. (Assuming Pisco was not supposed to be poking around in those files or his behavior was suspicious) Also, Vermouth may have already figured out Ai was at the party and told the boss something about it.