With Abraham and his seed Jehovah made a Covenant, which is called throughout scripture "the Promises". In it, God Promises, among other things, to give Canaan, with set boundaries, as an "everlasting possession". Another part of the Promises was that Israel would "possess the gates of his enemies", which means that Israel would rule over their enemies. Israel's part of the deal was the circumcision of all male seed. The situation when our Lord Jesus arrived in Israel was just the opposite. From around 730 BC the ten northern Tribes had been defeated, subjugated and carried off to Assyria. From around 600 BC the two remaining southern Tribes had been defeated and carried off to Babylon. Of these, only about 2.5% returned to build the Second Temple and Jerusalem. Israel at large had NOT received the Promises. The suffered under Babylonian rule, then under Medo-Persia, under Greece and now they were ruled and administered by Rome.
This morbid situation was due to another Covenant made with Jehovah - that of Law at Sinai. It demanded certain things to honor God, man and the Land, but Israel had disregarded this Law and the penalties of this Contract had driven Israel out of their Land and made those who returned, subjects of foreign kings. Although the Babylonian captivity had effectively dealt with Israel's main problem - idolatry, the offspring of those that returned from Babylon kept the Law in lip-service and not with their hearts and minds. The Pharisees "sat in Moses' Seat" and ruled the religious side of Israel with great words and empty deeds. They represented Israel, but were slaves of Rome. They represented the Law, but were despisers of the Law. They looked for their Messiah. But they wanted a Messiah who would deal with Rome, and not their sins.
As our Lord Jesus' fame spread the Pharisees felt that their grip on the little that was left of Israel, was slipping. They had no answer for this Jesus. So they used the one thing that they were guilty off to stir up the authorities and the people against Jesus - relations with Rome. They themselves were minions of Rome, but they tried to trap Jesus with the very Rome they were slaves of. If our Lord Jesus had said, "NO! Don't subject yourselves to Rome by taxation! You are free men", the Pharisees would have hastened to Pilate and reported a political and financial uprising by Jesus, the most prominent citizen of Israel. If Jesus had said, "Yes, you must pay taxes to Rome", the Pharisees would have hastened to the people and said that Jesus was an emissary of Rome and so stirred up Israel to stone Jesus.
Jesus' answer obliterated their position. Who had money with Caesars inscription??? Not Jesus! He did not partake of Rome. BUT THE PHARISEES HAD CAESAR'S MEANS AND CAESAR'S INSCRIPTION IN THEIR POCKETS! Who now was dependent on Rome? Who now traded with Rome's values? Who now was dependent on Rome to buy food? THE PHARISEES!!! And further ... Why were the Pharisees (and Israel) subject to Caesar??? BECAUSE GOD JUDGED THEM LAW-BREAKERS!!! Leviticus 26:15-17 taught that ...
15 "And if ye shall despise my statutes, or if your soul abhor my judgments, so that ye will not do all my commandments, but that ye break my covenant:
16 I also will do this unto you; I will even appoint over you terror, consumption, and the burning ague, that shall consume the eyes, and cause sorrow of heart: and ye shall sow your seed in vain, for your enemies shall eat it (TAXATION)
17 And I will set my face against you, and ye shall be slain before your enemies: they that hate you shall reign over you (CAESAR); and ye shall flee when none pursueth you."
The Pharisees claimed rule over Israel. They claimed to be upholders of the Law. they forced the letter of the Law on Israelies while making traditions themselves which made the Law of none effect FOR THEM. They claimed to be for a FREE ISRAEL, but has Caesar's superscription in their pockets! They claimed that they were for Israel but were for Caesar's trading system. Our Lord Jesus took their own cunning and exposed them for what they were - illegal religious rulers who forced a Law onto the common man while they broke it and were in bed with Caesar!