The Cheshire Cat has mysterious powers and constantly teleports from one place to another. He speaks in riddles and wears an almost permanent grin on his face. He also likes to move his body parts around in odd positions, mostly his head, to see the reaction of his audience.
The Cheshire Cat is definitely a strange character, talking in riddles and often confuses people who spoke to him. Even Roxas remarks this by saying, "That cat is a walking question mark." He often helps the characters, albeit indirectly, showing his neutral alignment. The fact that he talks in riddles and knows almost everything and anything in Wonderland proves that he is quite smart. In Kingdom Hearts 358/2 Days, he admitted that he is "mad".
The Cheshire Cat's perplexing personality that deems him as neither an ally nor enemy confuses many characters, including Maleficent and other related villains who, in the Kingdom Hearts manga, offered the Cheshire Cat a spot in their alliance. However, the Cheshire Cat refused, leaving the group upset and wonder whether he should be eliminated or not. However, this shows that the Cheshire Cat is more so a friend than a foe to Sora and his friends.
The Cheshire Cat is a bizarre, rather rotund cat with a perpetual grin. The cat's fur is striped purple and pink, a pattern that stops abruptly at his wrists and ankles. His mouth, hands, feet and the tip of his tail are all a very light pink color, while the fur on his head is ruffled at the top (obscuring his small ears) a solid red-violet. His eyebrows, which are always raised, are black, and his eyes are yellow. His nose is a dark rose color, and below it, are six grey whiskers, three on either side of the cat's upper lip, that are oddly off-center from the follicles. His hands and feet both seem to have opposable thumbs, along with three other fingers or toes.
Each of his digits sport short, black claws. The Cheshire Cat displays a high degree of balance and dexterity, usually standing on his hind legs and occasionally on his hands. Most notably, the Cheshire Cat is able to make parts of his body appear and disappear at will, remove his head from his shoulders and continue talking, occasionally balancing it on his feet during his handstands, or even balancing the rest of his body on the head itself.
The Cheshire Cat aids Sora and his friends during their time in Wonderland, guiding them not only in finding evidence of Alice's innocence, but also in finding the Trickmaster. His true intentions though, are not very clear, and he seems more interested in seeing how Sora would handle the challenges than seeing him succeed.
After Sora and company defeat the Trickmaster, the Cheshire Cat tells the party that Alice is no longer in Wonderland, and has been taken by the shadows. He then leaves, disappearing into the darkness.
Kingdom Hearts Manga
The Cheshire Cat tells the reader that he was recruited to join Maleficent's band of villains, but turned them down. This shows how he remains neutral in the conflict.
Chain of Memories
The Cheshire Cat appears as a figment of Sora's memories in Wonderland, created by Naminé, giving him advice on how to save himself from being executed by the Queen of Hearts in his characteristic riddles.
The Cheshire Cat assists Roxas and Luxord during their missions in Wonderland through riddles. He appears frequently, and on Roxas's last encounter with him, he asks the Cheshire Cat if he is a friend or a foe, to which the cat replies, "Neither... or both. It's quite up to you. Once you believe, truth and lie are quite the same thing. Let your heart decide- it's in your heart you must confide". In this quote, the Cheshire Cat alludes to Roxas's internal conflict in doing work as part of the Organization, and his questions about Organization XIII.
Once Data-Sora is in Wonderland, the Cheshire Cat reappears to converse with him and Alice, though made out of data. The Cheshire Cat gives hints about what Data-Sora should do next. He explains how words linked to Alice's memory are scattered across Wonderland, and how collecting them will help restore it.
After Data-Sora completes Alice's requests, the Cheshire Cat will appear once again, telling Data-Sora that "Funny thing about memories is that something will lie forgotten in your heart for ages- then one day, you'll remember. But then, a moment later, the memory may drift away again to wherever memories sleep", foreshadowing what appears to be Naminé's connection with the real Sora, or Sora's memories of Ventus, Terra, and Aqua.
The Cheshire Cat appears again in Castle Oblivion, where you have to solve a riddle he gives you. If you solve it, you get an Inkling.
He first appeared in Disney's "Alice in Wonderland", which was based on Lewis Carrol's "Alice's Adventures in Wonderland". The Cheshire Cat was one of the first people to actually care about Alice's problems. He thought that it was better to have fun and be brave then to have never tried at all, even if it killed you. This almost happened when he brought Alice in front of the Queen of Hearts.
The Cheshire Cat had a strange habit to appear and disappear as he wished and to take his head off and on, along with any other body part he wanted to rearrange at that time. The Queen of Hearts is said in the book to have tried to behead the Cheshire Cat, but was unable to because he took his head and walked off with it after it was sliced off singing something about Jabberwockies. This is a reference to the poem, the "Jabberwocky", also written by Lewis Carrol.
He spoke in riddles that only he understood, but were in fact very important to understand. In a way, he is the true power in Wonderland, as his very name struck fear into the natives, and he always knew what everyone in Wonderland was doing.