13 Then they sent to Him some of the Pharisees and the Herodians, to catch Him in His words.
14 When they had come, they said to Him, “Teacher, we know that You are true, and care about no one; for You do not regard the person of men, but teach the way of God in truth. Is it lawful to pay taxes to Caesar, or not
15 Shall we pay, or shall we not pay?” But He, knowing their hypocrisy, said to them, “Why do you test Me? Bring Me a denarius that I may see it.”
16 So they brought it. And He said to them, “Whose image and inscription is this?” They said to Him, “Caesar’s.”
17 And Jesus answered and said to them, “Render to Caesar the things that are Caesar’s, and to God the things that are God’s.” And they marveled at Him.
Also found in Matthew 22:15-22 and Luke 20:20-26.
For the Pharisees and Herodians to unite in a common cause was quite unusual. The Pharisees were strongly resentful of the Roman occupation of Palestine—particularly of Judea where the poll-tax was required (Matthew 22:17; Mark 12:14). In contrast, the Herodians strongly supported the Roman presence in the land, because this was the source of power by which the Herod family ruled. In whatever way Jesus answered their question, they assumed He must violate the tenets of one of the two groups. He would be proven guilty in the eyes of either the people (Luke 20:26) if He disagreed with the Pharisees, or the governor (Luke 20:20) if He disagreed with the Herodians. — Thomas, page 187.
catch (v.13) = to hunt and catch like a wild animal. Matthew used the word for “entangle”— “to snare or trap” birds.
The preamble is skillfully arranged with the view of disarming suspicion, and at the same time preventing escape. So independent and fearless a teacher of truth could not from fear of consequences either refuse an answer to honest and perplexed inquiries, or conceal His real opinion. — Wuest, page 231.
know (v.14) = positive knowledge, absolutely conviction
true (v.14) — true in the sense that He could not lie
lawful (v.14) — permissible, allowed, permitted (not really a question regarding civil or criminal law)
The Jews were not discussing the legality of paying poll tax to Caesar, but whether a Jew should do so in view of his theocratic relationship to God. They pressed for an answer, yes or no, as if there were no other possible answer. They hoped, in view of His Jewish background and teaching, that He would say no. That would involve Him at once with the Roman authorities. Such a reply, considering the present mood of the crowd, might put Him at the head of a rebellion (Acts 5:37) or at least would have made Him liable to a charge of treason (Luke 23:2). Had He given an affirmative answer, He would have incurred the displeasure of the Jewish crowds. — Wuest, page 232.
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