Hi everyone, I just want to put this out there. At the moment it only stands as a theory, something I've thought up. Before I start, let me just point out the two things that have been bothering me for a while inrelations to this topic. Firstly, why does Gin always imagine Sherry naked when he thinks about her? Second, why does he seem to get a kick out of hunting her, as if he is a huntsman hunting a sly and slippery fox but is not concerned when he fails?
These questions have been stuck in the back of my mind for so long mainly because I think Gin might have an overactive obsession with Sherry. For example, say we don't go by everything we know about Sherry, like her telling us that she didn't play a very big role in the BO and that she was only there to oversee experiments for the APTX-4869. Say we dismiss this and assume that Sherry was in fact a very important person in the BO, she had her own nickname, where as her sister Akemi did not. Same goes for Akai Shuuichi who had to get promoted for his alcoholic nickname Rye. I assume Sherry was so well known in the organisation that the lab she worked in had to be burned down because she managed to escape. This brings me to think that aside from Vermouth, maybe there was another Boss's favourite, i.e Sherry. Maybe the reason why Gin was so obsessed with her for a while was because just like Vermouth Sherry was also protected/shielded by the boss. In Volume 2 chapter 7 page 12, Gin says: 'She's(Sherry) is one of the top brains in our organisation...unlike you, she is an indispensable member.' So it is here that Gosho tells us Sherry is in fact very important after all which leads me to believe that Sherry was always a target for Gin; first sexually and now he wants her dead.
I hope I've still got all of your attention relating to the topic of this thread. What I've been trying to imply is that although Gosho is not giving us the full low down of what Gin's specific interests are for Sherry but I think Gin is playing a childish game of cat and mouse. First he could not harm her because she was a very important person in the BO, but now he has full permission from the boss to kill her. Therefore, now he can finally touch what was so out of his reach. While Sherry was in the BO her role gave her the power to reject Gin, compared to the other members in the BO such as Chianti, Korn and Vodka who are absolutely at his disposal, whereas Sherry and Vermouth had a mind of their own. On one occasion Gin has even said that if he could take down Vermouth he would but because she is the boss's favourite he can't. What I am trying to get at is maybe Sherry has always rejected Gin, maybe she managed to get into his head so much that his attraction for her became more of an obsession and violent hatred. He imagines Sherry naked because that is what he wishes but could never have, and so smartly Sherry managed to escape from right under his nose without the faintest idea that she shrunk into a 10-year-old girl's body. Gin has amazing detecting skills, but I'm sure his never managed to detect that.
In conclusion, to Gin Sherry has always been one step ahead of him, always just manages to slip right from his fingers. Gin probably enjoys this so much because it places a great challenge for him, something interesting, exciting, not always sure of the results and most of all something at first he wasn't allowed to have, but now he can. However, this time Conan is going to make sure that's the last thing that happens, yet again resulting into another cat and mouse chase.
I really hope you all understood what I just wrote and that it made a lot of sense, thanks for reading