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Avon, blakes 7

Spongebob would at first look like he is terrible and then suddenly obliterate his opponent (a grandmaster)

Deep Thought. It would only be beaten by the Earth. (Hitchhiker's guide to the galaxy)

Nah! He was even beaten by Kirk in one episode. By KIRK!

“I’ve calculated every move in a billion possible games. You always hang the queen.”

Yuki Nagato, though she'd cheat

There is a fan theory that Sherlock Holmes impersonated Harry Nelson Pillsbury at Hastings

Tommy Westphall

Winning the pooh