First Century Jewish culture had several subcultures, and we see a least three in these challenges. The Pharisees were ultra-orthodox, with many additional traditions that were intended to make breaking a law "impossible". The Sadducees were less orthodox, did not recognize the writings of the prophets as having authority equal to the Law of Moses, and were willing to accommodate (sometimes a euphemism for "compromise") Graeco-Roman culture. The Herodians were politically aligned with the family of Herod, and through them, with Rome. The Pharisees believed the Jews should be independent and a regional power, so they and the Herodians would have clashed as political opposites.
Pharisees' & Herodians' Challenge, Matthew 22:15-22
This challenge was fishy on its face. To be sure, the issue they posed to Jesus was one over which they would have argued, bitterly. But that they came to Jesus together, so that the opponents of what they thought were the only two possible answers were both present suggests some pragmatic collusion (both parties saw Jesus as a threat).
Jesus' answer reflected that He understood what they were up to, yet He still answered their question. And His answer - that God and government both have valid, non-conflicting, claims on people living under them - satisfied neither party, yet left them no room for retort. In delineating the proper, scriptural, relationship for a follower of God with God and government, Jesus answered the challenge, demonstrated that He understood the scriptures, and gave a clear principle to follow for believers in centuries to com.
Sadducees' Challenge, Matthew 22:23-33
The Sadducees came with a challenge that they thought showed that the idea of a resurrection (which they denied and Jesus had taught) conflicted with the Law of Moses. Evidently they thought they could confuse Jesus with a nitpicking, detailed, hypothetical situation. Instead of being confused by or entangled in the details Jesus showed them that they didn't understand the very scriptures they claimed to believe. Jesus' directness in pointing out their ignorance suggests to me that Jesus knew they didn't really care to understand the Law, except as it suited their purposes - following it outwardly when convenient, weaseling it when not, and using it as a clumsy weapon when faced with some one who disagreed with them.
Pharisees' Second Challenge, Matthew 22:34-40
The Pharisees' second challenge puzzles me. This was a very basic question, one a very young student should know how to answer! Did they think Jesus too educated to know? Did they think He was so deep into subtleties and details that He would not recognize the question as basic? Had they run out of "tough" questions but were not ready to beat a retreat? Regardless, Jesus gave them the correct answer, demonstrating both His knowledge and presence of mind under pressure. And Jesus used this and the previous questions as a springboard for his counter-challenge.
Jesus' Poser, Matthew 22:41-46
At least part of what the religious leaders had been doing had to do with their idea that Jesus was just a semi-educated bumpkin. The Jews in that day had a very rigorous process for selecting and training youth so that those who became teachers were the best of then best of the best. Jesus hadn't made the grade. Jesus had already turned this image against them in His responses to their questions, and now He put these "educated" leaders on the spot. Jesus had hit them in their public image, for the hypocrisy in their lives, and for their real heritage and character. Now Jesus hit them in what was supposedly their area of expertise, their knowledge and understanding of scripture.
His question was deceptively simple, in a couple of ways. The particular scriptures were very familiar, but they probably had never noticed - or just didn't bother to think about. Worse still, the answer to Jesus' question, the meaning of the two scriptures didn't fit their image of the kind of Messiah they wanted. And was consistent with things Jesus had claimed about Himself.
That shut the leaders up! What they imagined they could do to Jesus, He had done to them! And Jesus wasn't done with them!
Jesus' Condemnations: Religious leaders, Matthew 23:1-36; Jerusalem, Matthew 23:37-39
Jesus! Lit! Into! Them! He called them hypocrites, children of hell, blind guides, white washed tombs, descendants of murderers, brood of vipers! Do I need to say what He was thinking? He said exactly what He was thinking! Jesus told the religious leaders exactly what they were. Jesus warned the people just who they were following. And Jesus warned his disciples what dealings with those leaders would be like. Jesus ended this drama with a lament over Jerusalem and its looming fate, and then He left the temple.
All in all, this shows us that Jesus wasn't the dreamy idealist flower-smeller some imagine Him to have been. One can believe Jesus to have been a religion-crazed semi-lunatic (you have to ignore large parts of the Gospels), or one can believe Jesus acted in righteous and just anger (which is consistent with the rest of the Gospels), but dreamy idealist flower-smeller is excluded by Jesus actions and words on this day.
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