Matthew 22:16-20

Mat 22:16 (KJB)
And they sent out unto him their disciples with the Herodians, saying, Master, we know that thou art true, and teachest the way of God in truth, neither carest thou for any man: for thou regardest not the person of men.

Now two opposing forces have joined together to try and snare Jesus. The Herodians were those who supported the dynasty of the Herods and were in total opposition to the teaching and principles of the Pharisees plus they were friendly with the Romans. They came to Jesus with the pretended attitude of sincere seekers of truth hoping to find something in the speech of Jesus that would cause the masters of these disciples to indict Him on. They came to Jesus as if they were truly seeking by stating that they know He is true and teaches the way of God and that He is not a respecter of persons. Did they honestly think that Jesus did not know their true intentions? Since the Herodians backed Rome and the Pharisees were ritual and ceremony obsessed, they were hoping that Jesus would say something that would indeed offend at least one of the groups.

Mat 22:17 (KJB)
Tell us therefore, What thinkest thou? Is it lawful to give tribute unto Caesar, or not?

Since Rome had conquered Israel, as a vassal state to Rome it was normal for the Romans to exact a tax or tribute to be sent to Rome. There were three types of taxes that the Romans levied: 1) A land tax on money and property; 2) A toll tax in ports or cities; 3) A poll tax which was like a capital gains tax. The last one is the issue of this verse. The poll tax also represented subjection unto Caesar. They thought they had Him because if Jesus said no, then He would have been in trouble with the Herodians and Romans and if he said yes, then He would have been in trouble with the Pharisees.

Mat 22:18 (KJB)
But Jesus perceived their wickedness, and said, Why tempt ye me, ye hypocrites?

Even though they came to Jesus with such kind words and probably a religious demeanor of smiles, Jesus knew that they were truly venomous and were not concerned about the answer to that question. They were only concerned and hoping that somehow Jesus would snare Himself in His words. He unmasked their evil by publicly calling them hypocrites. A hypocrite is someone pretending to be something they are not and they pretended to be nice and have just motives for asking that question.

Mat 22:19 (KJB)
Show me the tribute money. And they brought unto him a penny.

Jesus gets ready to do another visible example and asks that a penny be brought unto Him. The coin here would have been the Roman Denarius that would definitely have the picture of the Emperor on it. I have a Roman Sestertius which has the picture of Emperor Domitian who reigned 81-96 A.D.

Back

Mat 22:20 (KJB)
And he saith unto them, Whose is this image and superscription?

Then Jesus asks them about whose picture was on the coin and the inscription. There would be a picture of whichever Emperor was reigning and a brief inscription about him. In this case it would have been Tiberius who reigned from 14-37 A.D. The Inscription would have read, “TI CAESAR DIVI AUG F AUGUSTUS” which translates “Tiberius Caesar, son of the divine Augustus.” Actually the Jews had denounced pictures on the coins because they claimed it was an engraved image and a violation of the second commandment.