I don't agree that the escaped prisoner would be re-entrapping himself by returning to the cave. He has already returned to the cave to try to bring enlightenment to those prisoners that remain. The prisoners then reject his message. This rejection could be caused by a lack of understanding of light. Because light cannot be understood without an opposite, dark, there would be extreme difficulties understanding anything with such a great contrast when the contrast that is present is that of shadow vs. fire light. It would be very difficult indeed.
Could not the escaped prisoner, out of concern for those that remain, start at the level of understanding that those prisoners have. This would take the escaped prisoner to sacrifice his time (as he seems willing to do by his return to the cave) and energy to convince those prisoners of the light.
To teach one must start on the level of the learner. In the cave, the prisoners are focused on the shadows. Why then would the escapped prisoner not use the shadows (something familar to the prisoners) as to tool to teach them. One of the main features of an allegory is that it can be seen as anything from a neat little story to a great learning tool. This allows the learner to start at his own level, and then grow. One can see this in their own reading of the "Allegory of the Cave". Not everyhing was understood on the first read through. Only after the time and effort of reading and pondering was a fuller understanding able to come.
These shadows are the conseptual basis for all that the prisoners have. Even Plato uses things that are familiar to bring us to greater light.
Vyachesla
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