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Matthew 22;

41 While the Pharisees were gathered together, Jesus asked them, 42 Saying, What think ye of Christ? whose son is he? They say unto him, The Son of David. 43 He saith unto them, How then doth David in spirit call him Lord, saying, 44 The LORD said unto my Lord, Sit thou on my right hand, till I make thine enemies thy footstool? 45 If David then call him Lord, how is he his son?

To my understanding, the term 'son' in Matthew 22, is a characterisation of a descendant of King David, as opposed to a literal son and presumably it was the same understanding that the Pharisees had, in addition to knowing that Messiah is at the same time a 'son of the Blessed one', Mark 14:61

So, was Messiah disputing the belief that He is a 'son' or a descendant of King David by His question?

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Jesus was not disputing the fact that he was a descendant of David. He presents the Pharisees with a paradox whose only solution is that He is both man (i.e. "son of David") and God (i.e. "Lord").

Rather than inquiring deeper into the Psalm, the Pharisees decline to ask him to explain and, in fact, never again ask Him any questions (v.46).

Theophylact (a Byzantine Greek commentator) explains this passage:

Since they thought He was a mere man, He overturns their belief and by means of the prophecy of David [Psalm 109:1 LXX] teaches the truth, that He is also the Lord, proclaiming His own divinity. For when the Pharisees said that the Christ was the son of David, that is, a mere man, He says, How then does David name Him Lord, and he does not simply name Him Lord, but "in spirit", that is, as revealed to him by the grace of the Spirit? He does not say this to deny that He is the son of David, but to show that He is not a mere man, descended only from the Davidic seed. The Lord asks these questions so that if they would answer, "We do not know," they might ask and learn; or if they would answer the truth, that they might believe; or if they could not answer, that they might be put to shame and leave, no longer daring to interrogate Him.

Explanation of the Gospel According to Saint Matthew

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Messiah asked this famous question;
1)on the back of knowing that scripture cannot be broken,
2)aware of an 'inspired' that said 'God cannot lie'.
So, if Luke's gospel is anything to go by, and it is, here is witness that originates from God Himself about His Messiah delivered through Gabriel, a famous angel of God, concerning Messiah's earthly descendancy and devine origins.

Luke 1:32 He will be great and will be called the Son of the Most High. The Lord God will give Him the throne of His father David.

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1 John 5:9
If we receive the witness of men, the witness of God is greater: for this is the witness of God which he hath testified of his Son.

Messiah is a spirit from eternity, Micah 5:2, written about as being Elohim, John 1:1-4, John 17 etc, elements on their own that could potentially make Him to be anyone in any era, as His will or His duties require it.

As the Head over the saints of the Most High, He is a being with a very peculiar nature, and that, in anticipation of the ultimate destiny for which Israel was chosen from many nations.
His duties, broad in scope and unlike any of any leader before Him, make His characterisation by a single human, be it an emperor, unfit for the purpose.

And so, the Most High foreseeing these problems that this peculiarity would cause, He accordingly set out to signify this Leader's coming and His peculiar nature in several places in the writings, for it's largely by symbolism that He communicates to fallible man spiritual complexities that also bear upon man's affairs.
Therefore Messiah is in many figures and characterisations. But even then, these are in mysterious details scattered throughout scriptures as Isaiah 28:10 says, implying that there are just a few overt expressions pointing to Messaih, leaving the bulk of them in mystified figures.

It's these details, upon which much depended and still depends to this day, that Messiah laboured to demystify amidst contradiction in one of His famous questions to the Pharisees.

Below is where it all starts concerning the His earthly origins and His duties;

2 Samuel 7:12-16
12 And when thy days be fulfilled, and thou shalt sleep with thy fathers, I will set up thy seed after thee, which shall proceed out of thy bowels, and I will establish his kingdom.
13 He shall build an house for my name, and I will stablish the throne of his kingdom for ever.
14 I will be his father, and he shall be my son. If he commit iniquity, I will chasten him with the rod of men, and with the stripes of the children of men
15 But my mercy shall not depart away from him, as I took it from Saul, whom I put away before thee.
16 And thine house and thy kingdom shall be established for ever before thee: thy throne shall be established for ever.

Cherry picking verses 13 and 16; a 'House' and a 'throne' to be established before the Most High forever is a messianic reference to Israel, or there would be collision with the writing below;

Hosea 3:4;
For the children of Israel shall abide many days without a king, and without a prince, and without a sacrifice, and without an image, and without an ephod, and without teraphim:

This was a prophecy aimed at the northern kingdom but whose words eventually overtook even 'her' sister in the south..

So Messiah wasn't denying His ancestral ties to Israel's most illustrious monarch, rather it was an attempt to open their understanding to the mystery of the Son of God, having found their take on scriptures very distorted and as a result, tangential to many moral implications and truths in the laws;

Ref; Matthew 23 with verses 16-22 as His highlight on their offense.

This thick mist in scriptures concerning Him was His to clear by what He said and did, yet in more significations, as these things are both the teachings and the judgments; Ref:Isaiah 6:10 and
1 Corinthians 1:18-19
Himself says;

Matthew 13
10 Then the disciples came to Jesus and asked, “Why do You speak to the people in parables?” 11He replied, “The knowledge of the mysteries of the kingdom of heaven has been given to you, but not to them.
12 Whoever has will be given more, and he will have an abundance. Whoever does not have, even what he has will be taken away from him.

An overt signification was to refer to Himself as a 'Son of man' and rarely in the 1st person, this pointing to the character of Shiloh as Genesis 49:10 teaches. The 'two' aren't a 'visual' two but as the Father and the Son are distinct yet manifest to men in one entity of the Son, so they ONE, and about whom is an elaborate signification in Numbers 10:3-6 depicting them as two 'silver trumpets' that 'call' the congregation of Israel to assemble and for the 'journeying'.

Numbers 10:3-6
3 And when they shall blow with them, all the assembly shall assemble themselves to thee at the door of the tabernacle of the congregation.
4 And if they blow but with one trumpet, then the princes, which are heads of the thousands of Israel, shall gather themselves unto thee.
5 When ye blow an alarm, then the camps that lie on the east parts shall go forward.
6 When ye blow an alarm the second time, then the camps that lie on the south side shall take their journey: they shall blow an alarm for their journeys.

To explain briefly a few symbols in what's going on here;

((To gather/assemble = indoctrinate, Matthew 23:37 and Rev 16:15-17; Silver denotes life/aspects of essence of men in respect with holiness, the purer the metal, the more holy; Isaiah 1:22 etc;
A trumpet and a horn are same idea, denoting a leader with 'powers,' as also a pillar denotes a leader; 1 Kings 7:21 and Rev 3:12.
The temple in Jerusalem signified the era of the Kingdom of the Most High in the earth when these '2' mysterious leaders would be manifest as two imposing pillars by the door; a door is teacher. They are both the door/entrance and the pillars, the leaders in that age that Ezekiel's pillars, doors, courts etc, depict.
Now by 'two' it doesn't mean a visual 'two', but as the Father and the Son are distinct, yet manifest in One individual, so it is with Shiloh and Judah.
Ref : Gen 40:10 + Psalm 108:8.))

So when one of the 'silver trumpets' is 'blown', it denotes a generation of the congregation of Israel when one of these leaders would be manifest for 'gathering' leaders, the so called first fruits, in the age to come.
Ref; 1 Corinthians 15:23 and Revelation 14:4

But when both 'silver trumpets' are blown it denoted an age when both these 'two,' or 'dual character' will be manifested for the sake of 'gathering' ALL the congregation of Israel in such a time as when Israel will be as good as the gentiles around them. This is why we have 'Galilee of the Nations' despised by the Jews, but which area Messiah chose for a home, this reflected in these sayings;

Matthew 2:23
..and he went and lived in a town called Nazareth. So was fulfilled what was spoken through the prophets: “He will be called a Nazarene.”
John 1:45
Philip found Nathanael and told him, “We have found the One Moses wrote about in the Law, the One whom the prophets foretold — Jesus of Nazareth, the son of Joseph.”

And to go to Galilee on arising from the grave;

Mark 16:6-7 6 And he saith unto them, Be not affrighted: Ye seek Jesus of Nazareth, which was crucified: he is risen; he is not here: behold the place where they laid him.
7 But go your way, tell his disciples and Peter that he goeth before you into Galilee: there shall ye see him, as he said unto you.

Of His most esoteric scriptural illustrations dramatised with His life before His audience, but whose significations were lost on many including His main disciple, we have;

A) John 13
7 Jesus answered and said unto him, What I do thou knowest not now; but thou shalt know hereafter.
8 Peter saith unto him, Thou shalt never wash my feet. Jesus answered him, If I wash thee not, thou hast no part with me.

B) And the two notable ones being Zachariah 9:9 and Isaiah 9:2 which is about Galilee.

Zachariah 9:9
Rejoice greatly, O daughter of Zion; shout, O daughter of Jerusalem: behold, thy King cometh unto thee: he is just, and having salvation; lowly, and riding upon an ass, and upon a colt the foal of an ass.

By 'sitting' on 'two' donkeys, He was signifying the same aspect as that, forexample, of both Joshuas, of Ephraim and Levi, who undoubtedly are messianic depictions but not from Judah, which tribe is expressly written about as messiah's tribe, Micah 5:2 and Revelation.
Now it isn't a coincidence that also Messiah's natural father was a 'Joseph' not a 'Judah', pointing to shiloh, also an aspect to Joshua of Ephraim who closely depicts this Shiloh in his captaincy over Israel and eventually leading them into the promised land.

Isaiah 9:2
The people that walked in darkness have seen a great light: they that dwell in the land of the shadow of death, upon them hath the light shined

To explain this prophecy by illustration, He chooses Galilee among the gentiles as a home, and not Bethlehem of Judah about which it's expressly written of Him as being His origin. Not even once(atleast its not written) did He defend His devine origins by mentioning Bethlehem Judah as His birth place, as its written of Him in Micah 5:2, and as the gospels affirm.
Incidentally there are two Bethelems, and no, its NOT a coincidence either!
In a nutshell Messiah by these dramatisations depicted circumstances of 'two' characters seperated by time.
Isaiah 9 depicts His 'other' circumstances.

In closing, let's look at some of the nuances in two scriptures that depict messiah by David the king;

Jeremiah 23:5
"Behold, the days are coming," declares the LORD, "When I will raise up for David a righteous Branch; And He will reign as king and act wisely And do justice and righteousness in the land.

Jeremiah 30:9
But they shall serve the LORD their God and David their king, whom I will raise up for them.

Unobservant readers simply stampede through these two distinct writings. To branch 'in the earth' is a mark of higher spirits, including The LORD, as opposed to 'branching upward in heaven', which is a characteristic of righteous sons of men, but for the wicked it never makes it up because it withers by wickedness,Job 18:16, John 15:4-5;

So, one says a 'David the king', and another says a 'Branch to David'.
As a Branch of Jesse isn't quite Jesse, so is this Branch to David not David, as also the Branch of the LORD is not the LORD.
So to whom do these scriptures point to as the Branch to David, already 'David the King' we know?
This isn't mere parallelism or a random choice of words as commonly thought. It's a connotation of core truths about the nature of messiah .

His zeal to educate or gather was what prompted His question to the Pharisees, who often caused Him frustration and grief because they were blind and didn't know it.

Isaiah 49:
4 But I said, "I have toiled in vain, I have spent My strength for nothing and vanity; Yet surely the justice due to Me is with the LORD, And My reward with My God."
5 And now says the LORD, who formed Me from the womb to be His Servant, To bring Jacob back to Him, so that Israel might be gathered to Him (For I am honored in the sight of the LORD, And My God is My strength),

Yet He achieved it in a few (John 3:1)that are written of below;

Matthew 16
17 Jesus replied, “Blessed are you, Simon son of Jonah! For this was not revealed to you by flesh and blood, but by My Father in heaven. 18 And I tell you that you are Peter, and on this rock I will build My church, and the gates of Hades will not prevail against it.

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