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Cheshire is a free spirit. He cares little for things like politics, but that does not mean that he doesn't know about them. He will seem to flip back and forth, helping either side as he pleases or sees entertaining. Despite this, he does take sides and will help out the group he has taken favour with, appearing when his help is most required. That still doesn't mean that he will make things simple. He wraps his advice in riddles and nonsense; he has to keep things interesting after all. This loyalty is not something that should be relied on though, since he prefers to keep his actions unpredictable. He might still help the other side if he thinks that those who he has really sided with will be able to overcome the difficulties caused by his subterfuge.
Cheshire is best known for his smile, and for good reason. He usually only shows two expressions; smiling, and smiling wider. That is not to say that he is always is happy. He's just as fickle as most cats, though he just tends to “grin and bare it”. One of the things that bothers him the most though is not being in-the-know about things. In Wonderland he passed between all parties, meaning that he knew what was always going on. This way it was easier to manage things, as well as to play with people's heads.
He also dislikes partaking in any actual physical fight. He isn't above fighting however, if he were forced to. He has no moral issue with fighting, or any other sort of issue with it, but he just normally sees no need to get involved in the dangerous part. That sort of thing was for the cards, not the cats.
He would much rather stick to the mind games. While he enjoys the challenge presented by someone not easily ruffled, he doesn't like not being able to ruffle someone either. He'll never get bored of making a person flustered- especially not if they're fond of trying to order him to be beheaded- but his favourite interaction is someone who can twist words just as well as he can.
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