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I think Vermouth knew the Akai family in the past. During the mystery train case, Vermouth, as Scar Akai, said to Sera 'You haven't change at all, Masumi.' Not matte how well Vermouth can impersonate Akai, she would have no way of knowning how Sera was in the past and say with such confidents that she hasn't changed, if they have never met before, since I except that Akai keep his family and his job as FBI agent very much apart. Therefore I think that at some point in the past Vermouth have met Sera once.
AnimeOtakuDrew posted a topic in GeneralOkay, so I have been watching through everything Conan (currently up to episode 730) and I have noticed something of a pattern. Correct me if I'm wrong, but it seems that nearly everyone that is trying to bring down the Black Organization has some personal reason for doing so. Jodie-sensei's father was killed by the Organization. Haibara/Miyano Shiho's sister (And possibly her parents as well) was killed by them. Andre Camel is dedicated to Akai after blowing his cover in the Organization, and Wil thus do anything to help him stop them. Hondou Hidemi's father died because of the Organization (even though they didn't directly kill him). And Conan, of course, was poisoned by them and reverted to a child's body. The most notable omissions from that list are James Black (who I have a theory about, though I won't get into it here) and Akai Shuichi. But why does Akai want so badly to take down the Black Organization? Well, let's start by looking at the facts. The FBI' s search for the Organization is unofficial. What does that mean to this discussion? Well, since it's not an official operation, Akai couldn't have simply been assigned to the case. For him to be this deeply involved in a case that he wasn't assigned to, it has to be personal. Next, Sera Masumi is Akai's sister. How is this relevant to Akai's connection to the Organization? Well, Sera seems to know Conan's secret even though she has never been told and is not at all shocked by or disbelieving of the idea that the high school detective has been somehow turned into a child, meaning she must have seen something similar before. The prevalent theory seems to be that the mysterious Mary (whom I actually have yet to see, though I know about through accidentally reading some spoilers) is Sera's mother, and presumably Akai's. The most commonly cited evidence is that Sera calls her Mama. It also seems as though Sera and Mary on on the run (according to those same spoilers I mentioned before). But why? This is where everything comes together to form one theory. Is it possible that Mary was formerly associated with the Black Organization? Perhaps she betrayed them, or simply outlived her usefulness, and they decided to eliminate her. What if, to do so, they gave Mary APTX-4869, or an earlier form of the drug, but rather than killing her, it reverted her to a child's body just like Conan and Haibara? It is commonly accepted that APTX-4869's de-aging side effect reverts a person specifically to a child's body, rather than just knocking off 10 years. If we figure that, like Conan and Haibara, Mary was made to appear about 7 years old by the drug, and assume that aging would happen normally from that point, it can be deduced that Mary was given the drug about 5-6 years before the present story, as she now appears to be about 12 or 13. The timing of this is important because it is the key to everything. After being poisoned by the Organization, Mary goes to her family, most likely out of fear that the Organization will harm them as well. Akai then has Sera and their mother go into hiding while he goes after the Organization to stop them and/or get revenge for their attempted murder of his mother (btw, do we know what happened to the father? Is it possible that he too was killed by the Organization?). Why is the timing important? Because after those events, Akai needs time to find and get close to the Organization to infiltrate them (remember, the Black Organization is supposed to be a secret criminal syndicate that nobody outside of their own membership knows about, so such a group would be very difficult to find). Perhaps he was already FBI at the time his mother was poisoned, or perhaps he joined so he could make use of their resources to aid in his search, t which time he learned about other agents bearing a personal vendetta against the Organization. Either way, with the help of the FBI, Akai was finally able to track them down and gain their trust enough to join (though the events with agent Camel show they still felt it necessary to test him). From that point, events played out as we have seen on the show. So, in short, my theory is an extension of the "Mary was poisoned by the Organization" theory, stating that the poisoning of his mother is the reason Akai is so dedicated to bringing down the Black Organization. What do you guys think? Plausible? Possible? Let me know?