When used in its intended form, "crazy like a fox" is an oxymoron meaning seemingly foolish but in fact extremely cunning. If you call someone "crazy like a fox" you are saying that person is sly and capable of outwitting others. For example: "That John McCain (or more accurately, the Karl Rove political machine) is crazy like a fox for choosing Sarah Palin as his running mate."
The fox has been celebrated for centuries as a crafty animal — especially by the British during the hunt. While a fox's actions may appear bizarre to the average onlooker, he is often acting in a brilliant manner to save himself.
The animal's wiles were first noted in the "Trinity College Homilies," dating from the 12th Century. The expression gained modern currency when American humorist S.J. Perelman selected it for the title of his 1944 book.
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