Matt 22:1-2 And Yeshua (Jesus) answered and spoke to them again by parables, and said, the kingdom of heaven is like a certain king, which made a marriage for his son,
spoke to them again - this appears to be a continuation of the previous chapter. (Matt 21:23)
The king in this story is G-d the Father. His Son is Yeshua.
Matt 22:3-6 And sent out his servants to call them that were bidden to the wedding: and they would not come. Again, he sent forth other servants, saying, Tell them that are bidden, Behold, I have prepared my dinner: my oxen and my fatlings are killed, and all things are ready: come to the marriage. But they made light of it, and went their ways, one to his farm, another to his merchandise: And the remnant took his servants, and entreated them spitefully, and slew them.
Those who were initially called to the wedding were the children of Israel. The servants were the prophets of the Tanakh period who were, in many cases, rejected and some were even put to death.
Yeshua was also rejected and put to death. (His death, of course, was part of G-d’s plan for our redemption.)
Matt 22:7 But when the king heard about it, he was furious: and he sent out his armies, and destroyed those murderers, and burned up their city.
Some believe that this is referring to the destruction on Jerusalem in 70CE (AD).
This generation was not worthy to receive the Mashiach. He would have to come back to a later generation.
Matt 22:8-10 Then he said to his servants, The wedding is ready, but they which were bidden were not worthy. You go therefore into the highways, and as many as you will find, bid to the marriage. So those servants went out into the highways, and gathered together all as many as they found, both bad and good: and the wedding was furnished with guests.
Here the good news is extended to the gentiles too.
Matt 22:11-12 And when the king came in to see the guests, he saw there a man which had not on a wedding garment: And he said to him, Friend, how did you get in here not having a wedding garment? And he was speechless.
The “wedding garment” is the Righteousness that comes from accepting Yeshua as ones Mashiach. This man, though he was invited to the wedding, rejected the wedding clothes provided for him by the King. This was a great insult to the king.
Matt 22:13-14 Then the king said to the servants, Bind him hand and foot, and take him away, and cast him into outer darkness; there will be weeping and gnashing of teeth. (more murmuring.) For many are called, but few are chosen.
The man’s rejection of the King’s provision was unthinkable and he was cast out of the celebration. There are many who believe that they can come before the King of the Universe by their own mitzvahs (good deeds). They think that they will be considered righteous. They, like the man in the story, will be speechless. They will be cast out of the presence of HaShem into outer darkness.
Matt 22:15 Then the P’rushim (Pharisees) went away and put together a plan to trap Yeshua with His own words.
His teaching was truth and perfection. They had a hard time trying to entangle Him in His words and teaching.
The twenty-second letter of the Hebrew alphabet is Tahv - truth; perfection
Matt 22:16 They sent their disciples to Him along with the Herodians. "Teacher," they said, "we know you are a man of integrity and that you teach the way of G-d in accordance with the truth. You aren't swayed by men, because you pay no attention to who they are.
The Herodians were not a religious group but a political party that supported the Roman-backed Herodian dynasty. The P’rushim (Pharisees) did not like the Herodians but teamed up with them in order to entrap Yeshua.
It did not matter to Yeshua the opinion of men. Many today care more about the teaching of false teachers or teachers they want to hear say nice things to them or say that their place with Adonai is secure. It does not matter what the opinion of man is in this regard. It does not matter what you think or what I think. What matters is what the total Word says by studying it and praying for wisdom from HaShem. The complete Bible needs to be studied.
Matt 22:17 Tell us then, what is Your opinion? Is it right to pay taxes to Caesar or not?"
Here is a loaded question. They figured He could only say “yes” or “no”. If He answered “yes” He would be going against the Jewish nation. If “no”, He would be going against the Roman government.
Matt 22:18-22 But Yeshua perceived their wickedness, and said, Why are you trying to trap me, you hypocrites? Show me the tribute money. And they brought to Him a denarius. And He said to them, whose is this image and inscription? They said to Him, Caesar's. Then He said to them, Give to Caesar the things which are Caesar's; and to G-d the things that are G-d's. When they had heard these words, they marveled, and left Him, and went their way.
Denarius - this was about a day’s pay for a Roman Soldier.