What does Matthew 22:16 mean?
ESV: And they sent their disciples to him, along with the Herodians, saying, “Teacher, we know that you are true and teach the way of God truthfully, and you do not care about anyone’s opinion, for you are not swayed by appearances.
NIV: They sent their disciples to him along with the Herodians. 'Teacher,' they said, 'we know that you are a man of integrity and that you teach the way of God in accordance with the truth. You aren't swayed by others, because you pay no attention to who they are.
NASB: And they *sent their disciples to Him, along with the Herodians, saying, 'Teacher, we know that You are truthful and teach the way of God in truth, and do not care what anyone thinks; for You are not partial to anyone.
CSB: So they sent their disciples to him, along with the Herodians. "Teacher," they said, "we know that you are truthful and teach truthfully the way of God. You don't care what anyone thinks nor do you show partiality.
NLT: They sent some of their disciples, along with the supporters of Herod, to meet with him. 'Teacher,' they said, 'we know how honest you are. You teach the way of God truthfully. You are impartial and don’t play favorites.
KJV: 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.
NKJV: And they sent to Him their disciples with the Herodians, saying, “Teacher, we know that You are true, and teach the way of God in truth; nor do You care about anyone, for You do not regard the person of men.
Verse Commentary:
The Pharisees want Jesus out of the picture one way or another. Despite His indirect—and, according to them, blasphemous—claims to be the Messiah and the Son of God, they can't arrest Him directly. Jesus is just too popular with the people for the moment. Earlier encounters showed that these religious leaders are more interested in political power than in honesty (Matthew 21:25–27). If they can get Him to say anything that sounds like rebellion against Rome, however, the Romans might remove Jesus for them. The Roman Empire was more than willing to execute Jewish rebels attempting to start an uprising.

Jesus, of course, was not trying to cause an uprising (John 18:36). That's one reason this plot by the Pharisees will not work. Still, they take a shot. They send some of their disciples to Jesus, along with representative from a group known as the Herodians. These Jews were loyal to the Herods and wanted Rome to give the kingship of Israel back to them. To that end, they did not want to do anything that would make Rome feel threatened by the Jewish people.

This mixed group approaches Jesus and begins with flattery. They respectfully call him "Rabbi," meaning "Teacher." They flatter His teachings and wisdom, as well as His independence and bravery. The setup makes it seem as if they are asking Him to settle a dispute between them and the Herodians. In political arenas, this kind of trickery is common; the group is trying to lower Jesus' guard by saying He is so smart and truthful and unworried about what others think that He is the perfect arbiter for the question they are about to pose.

Likely, the Pharisees assumed Jesus would not believe any flattery they might use. So, they sent their students, rather than approach Jesus directly. In their minds, Jesus was more likely to fall to flattery from younger people. Of course, He does not, and would not (Matthew 22:18).
Verse Context:
Matthew 22:15–22 is a famous event, containing Jesus' response to the issue of taxes. This moment is also depicted in Mark 12:13–17 and Luke 20:20–26. In that context, Jewish people resented being forced to pay those fees to Rome. This makes the challenge a trap: the Pharisees want Jesus to make an unpopular statement or open Himself to arrest for rebellion against the Roman Empire. Instead, Jesus points out that the Roman denarius has Caesar's image on it. He then tells the people to give Caesar what is his and give God what is God's. This subtly implies that we should give ourselves to God, since we bear His image (Genesis 1:27; Matthew 22:37).
Chapter Summary:
Continuing a dialogue with hostile religious leaders, Jesus tells a parable comparing the kingdom of heaven to a wedding feast which ends up being attended by those not initially invited. He answers trick questions about taxes, marriage, resurrection, and the Law of Moses. These responses are the source of common English idioms such as "render to Caesar…" and "many are called but few are chosen." Finally, Jesus asks how the Messiah can be both the son of David and the Lord of David. None can answer Him, so they stop challenging Him in public.
Chapter Context:
This chapter extends an exchange between Jesus and several groups of religious leaders in the temple. The previous chapter concluded with two parables about the failures of the religious leaders. This chapter begins with a third parable, about chosen guests who refuse to attend a wedding feast. Jesus then fields questions from several religious groups, who fail in their attempts to trip Him up. His wise and profound answers silence all of them. At this point, Jesus launches into a full-throated condemnation of the Pharisees in chapter 23.
Book Summary:
The Gospel of Matthew clearly shows the influence of its writer's background, and his effort to reach a specific audience. Matthew was one of Jesus' twelve disciples, a Jewish man, and a former tax collector. This profession would have required literacy, and Matthew may have transcribed some of Jesus' words as they were spoken. This book is filled with references to the Old Testament, demonstrating to Israel that Jesus is the Promised One. Matthew also includes many references to coins, likely due to his former profession. Matthew records extensive accounts of Jesus' teaching, more than the other three Gospels.
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