It wasn't uncommon for the slots, that the metal tabs of the case go into, to get bent or chewed up because they were the only things attaching to Kindle to the case. Have a look at them and see what condition that are in. Might have also pulled free from the circuit board. You should be able to measure a voltage across the slots when the Kindle is on. If there's enough gap you might even be able to measure on the bare parts of the case tabs while the Kindle is attached. Then you'd know if power is getting to the case.
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