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Fordim makes some excellent points about the nature of Middle earth precluding the existence of a true Trickster figure, but I wonder whether Tolkien, like Blake's analysis of Milton 'was on the devil's side without realising it'. He does introduce characters like Saruman who in a way wants to break free of the clearly defined rules & make up his own. He desires to 'break the Light'. Maybe he simply finds the 'rules' too restrictive & is trying to introduce chaos into the ordered world & find his own kind of freedom? Bombadil seems not to take the rules into account either, & simply go his own way. He certainly doesn't seem to live according to any pre-defined philosophy & simply lives out his own nature. I'm not sure he thinks of OMW or even the Barrow wight as 'evil' more as nuisances who need to be dealt with because they bother him.
Certainly he is not a typical Trickster - if there is such a thing - but he isn't 'good' by choice - he isn't aligned to the Good as such, he just happens to do good to the Hobbits he meets.
I don't know where I'm going with this...
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