It seems any interpretation of the passage needs to at least answer the following two questions:
1) What was the trap set by the question? ("plotted to entrap him")
2) How did Jesus escape/avoid the trap? ("they were amazed; and they left him and went away")
According to a common interpretation that I've heard, the dilemma was between answering "don't pay your taxes" and being handed over to the Romans, or answering "pay your taxes" and having the populous and/or followers upset and reject Jesus. So whichever Jesus chose, they would cry, "Gotcha!" And then Jesus' answer is commonly interpreted as being equivalent to "Pay the taxes." But if Jesus just picked the latter fork of the dilemma, why didn't the questioners clap their hands and say, "Aha! Gotcha."? Why instead were they silenced in amazement and simply left? This interpretation isn't a satisfying answer to my two questions. There were other incidents in the Gospels where Jesus is asked a question where either answer is a gotcha, and Jesus cleverly avoids the trap. So what is it here?
I have some ideas for answers to these questions, but I'd like to see what other people think first.
Some possibly related issues:
I find it interesting that the question is not whether paying taxes is required, but whether it is even permitted ("lawful").
A third question that may need to be answered in conjunction with the first two:
3) What was the questioners' hypocrisy?
What was the purpose of the questioners' praise of Jesus before posing the question?
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