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Jailbreaking has nothing to do with your ability to sideload content onto the Kindle. Jailbreaking lets you run 3rd party code on it, and thus run programs like KOReader. That lets you read EPUB format files directly on the Kindle with no conversion to a Kindle format. You can use USB to put all the random files you can fit on any Kindle, stock. The stock Kindle UI and reader will just ignore everything that it doesn't recognize.
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