The Pharisees did not want to pay taxes to Caesar, but the Herodians thought it was important: and neither of them had any desire to honour Jesus as King.  So, they set a trap: if Jesus agreed with the tax, He would be discredited as God's spokesman; if He denounced the tax, it would be treason (and punishable by death).  What Jesus saw in both groups was hypocrisy – pretending to be what they were not.  He always knows when someone is a fake.

Questions put people under a spotlight.  The religious leaders who wanted Jesus dead, asked one question, 'Should we pay or shouldn't we?'.  Jesus asked three questions in return.  The first highlights their motives, the other two expose their weak logic.  The traps were obvious, but why did they want to trap Him?  They knew that there was no way they could produce any evidence of wrongdoing: Jesus lived a perfect life.  But if they could get Him to say something which contravened either the Jewish or Roman Law, then they needed no evidence – Jesus would condemn Himself (Mark 14:61-64).  

Asking whose image and whose name was on the coin - revealed that they had not understood their own question.  If the coin belonged to Caesar, then it should be given back to him.  Where truth is in short supply, inconsistencies multiply as they did at Jesus' trial (Mark 14:56).  But Jesus' classic answer defeated their plot.  They could do nothing but be amazed at the way He answered.  It would have been reasonable for them to hold up their hands and admit defeat.  Intellectually, morally and spiritually Jesus was infinitely superior to them.  But more than that: He was the embodiment of truth: He knew everything, including everything they were thinking, and He knew how to expose their hypocrisy.  They embodied untruth - their words revealed their motives: their questions did not search for knowledge, but for a way to destroy the Son of God.

We should not be surprised if people want to discredit us and Jesus by asking 'clever' questions.  Their purpose is not to search for knowledge  or God's wisdom, but to trap us so that they can claim to have proved that God does not exist, Jesus is not God, Jesus did not die on the cross, and did not rise from the dead.  Like those who tried to trap Jesus, the purpose of their questions is to avoid any suggestion that they are morally accountable to Him.  How do we answer?  Firstly, be prayerfully prepared to talk positively about Jesus (1 Peter 3:15).  We should expect challenges so we should trust in the Lord and rely on the Holy Spirit to guide our minds and lips (Mark 13:11).  Often, asking another question produces more thought than an answer.