This was a trap, not a search for guidance. Matthew says the plan was to "entangle him in his talk" (Matthew 22:15), and Barnes explains that the word means to ensnare, the way birds are caught in a net. Either answer could be used against Him. In Barnes' words, "If he should say it was not lawful, the Herodians were ready to accuse him as being an enemy of Caesar; if he said it was lawful, the Pharisees were ready to accuse him." Luke adds that they hoped to "deliver him unto the power and authority of the governor" (Luke 20:20). The first question, "What thinkest thou?", invited Him to commit Himself; the second gave Him only two doors, and both were closed.

Jesus "perceived their wickedness" and asked, "Why tempt ye me, ye hypocrites?" (Matthew 22:18). He asked to see "the tribute money," and they brought Him a penny (Matthew 22:19). He asked whose image and superscription it bore, and they said, "Caesar's" (Matthew 22:20-21). Then He answered: "Render therefore unto Caesar the things which are Caesar's; and unto God the things that are God's" (Matthew 22:21). "When they had heard these words, they marvelled, and left him, and went their way" (Matthew 22:22).

"Tribute" is kensos, a word borrowed from the Latin census. Thayer defines it as the tax levied on individuals and paid yearly. Barnes notes that this was the tax paid to the Roman government, and that "Caesar" had become the title of every emperor after Julius Caesar; Tiberius was reigning at the time.

The two groups who came together were not natural allies. Barnes says it is not certainly known who the Herodians were; they probably took their name from Herod the Great, and perhaps they were first a political party that came to hold some of his peculiar opinions. Matthew Henry notes that although the Pharisees and Herodians were opposed to each other, they joined together against Christ. "Lawful" (exestin) means permitted: they asked, as Gill explains, whether it was lawful "according to the law of God."

The question assumed Jesus had to choose between God and Caesar. His answer refused that frame. He did not dodge the question; He answered it more deeply than they asked it. Matthew Henry observes that Christ did not set Himself up as a judge in such matters, "for his kingdom is not of this world," yet He taught "peaceable subjection to the powers that be."

The chief priests and elders had already questioned His authority (Matthew 21:23), and the test questions keep coming. The Sadducees come next (Matthew 22:23), then a lawyer (Matthew 22:35), and at last "neither durst any man from that day forth ask him any more questions" (Matthew 22:46). Each trap meant to catch Jesus became a showcase of His wisdom.