Why was no one able to recognize Jesus as Messiah using prophesy, yet we believe end times prophesy will be easier to clarify?

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The reason the leaders and elders were not able to identify Jesus as Messiah is that God made them incapable of understanding what was written about the Messiah.

Isaiah prophesies against Israel:

Isaiah 29:10-16

For the Lord has poured over you a spirit of deep sleep,
He has shut your eyes, the prophets; And He has covered your heads, the seers.

The entire vision will be to you like the words of a sealed book, which when they give it to the one who is literate, saying, “Please read this,” he will say, “I cannot, for it is sealed.” Then the book will be given to the one who is illiterate, saying, “Please read this.” And he will say, “I cannot read.” Then the Lord said,

“Because this people draw near with their words
And honor Me with their lip service,
But they remove their hearts far from Me,
And their reverence for Me consists of tradition learned by rote,
Therefore behold, I will once again deal marvelously with this people, wondrously marvelous;
And the wisdom of their wise men will perish,
And the discernment of their discerning men will be concealed.”
Woe to those who deeply hide their plans from the Lord,
And whose deeds are done in a dark place,
And they say, “Who sees us?” or “Who knows us?”
You turn things around!

By "you turn things around", he means that it is for the Lord to conceal things from men, and not men to conceal things from the Lord:

Psalm 25:2 It is the glory of God to conceal a matter, But the glory of kings is to search out a matter.

The leaders of the people, however, had been acting unjustly as though they could hide their actions from God. This is turning things on it's head. So, God says he is going to "deal marvelously," that is, he is going to act contrary to their expectations. In short, he is going to hide what he is doing from them. The psalmist agrees that it defies expectation:

Psalm 118:22-24 The stone which the builders rejected
Has become the chief corner stone.
This is the Lord’s doing;
It is marvelous in our eyes.
This is the day which the Lord has made;
Let us rejoice and be glad in it.

This theme of a lack of understanding of the Prophets is common throughout the prophets, especially Isaiah. At the end of Chapter 52 and beginning of 53, Isaiah speaks for the prophets:

Kings will shut their mouths on account of Him;
For what had not been told them they will see,
And what they had not heard they will understand.
Who has believed our message?
And to whom has the arm of the Lord been revealed?

These questions are rhetorical, and are exclaimed in woe as though he is saying, "we declare these things, but who is even listening?"

On the contrary, we are made so that we can understand- by the Spirit.

1 Corinthians 2:6-16 Yet we do speak wisdom among those who are mature; a wisdom, however, not of this age nor of the rulers of this age, who are passing away; but we speak God’s wisdom in a mystery, the hidden wisdom which God predestined before the ages to our glory; the wisdom which none of the rulers of this age has understood; for if they had understood it they would not have crucified the Lord of glory; but just as it is written,

“Things which eye has not seen and ear has not heard,
And which have not entered the heart of man,
All that God has prepared for those who love Him.”

For to us God revealed them through the Spirit; for the Spirit searches all things, even the depths of God. For who among men knows the thoughts of a man except the spirit of the man which is in him? Even so the thoughts of God no one knows except the Spirit of God. Now we have received, not the spirit of the world, but the Spirit who is from God, so that we may know the things freely given to us by God, which things we also speak, not in words taught by human wisdom, but in those taught by the Spirit, combining spiritual thoughts with spiritual words.

But a natural man does not accept the things of the Spirit of God, for they are foolishness to him; and he cannot understand them, because they are spiritually appraised. But he who is spiritual appraises all things, yet he himself is appraised by no one. For who has known the mind of the Lord, that he will instruct Him? But we have the mind of Christ.

We can understand the Spiritual things in spiritual ways because we are taught by the Spirit, and indeed if we are in Christ we have the mind of Christ. At the same time, it's obvious that there are disagreements about what will and will not happen, how it will happen, and when it will happen. Paul says that factions reveal who is approved by God, and who is not:

1 Corinthians 11:19 For there must also be factions among you, so that those who are approved may become evident among you.

So in closing, we can understand the things of the Spirit because we have the Spirit. If we do not have the Spirit, we cannot understand them, like the spiritual leaders of Israel did not understand them.

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It is important to note the nature of the prophecies themselves. The Old Testament gives very conflicting prophecies about the Messiah. To briefly look over them, here's an outline of a few of them:

  • He was to be a rejected Messiah
  • He was to be a betrayed Messiah
  • He was to be a ruler of all nations
  • He was to come in power 'on clouds'
  • He was to come in weakness 'on a donkey'
  • He was to be a teacher of the Gentiles
  • He was to be a Sacrifice for the sins of Israel.

If you notice, many of these prophecies seem to contradict each other. So to reconcile these apparent contradictions Christians, who believe Christ to be the Messiah for His fulfillment of so many of these prophecies and most importantly His death and resurrection, hold that these prophecies speak of one Messiah who exists and reveals Himself in two capacities, or at two different points in time, under distinct conditions.

In order to answer your question regarding why most people did not realize Christ to be the Messiah until such was revealed to them, it is important to recognize what prophecies were being fulfilled by Christ in His first appearance, or in other words what type of Christ was to be seen in the first coming; the humble and betrayed or the glorified and praised. The answer to this question is clear; Christ fulfilled the prophecies of the 'suffering servant' who faced rejection, betrayal, death and resurrection. As such, Christ's main purpose in His first coming to this world was not to bring about the final elucidation, peace and clarity (which can be assumed to occur in the second coming, along with other prophecies that have yet to occur) but rather to establish His Church through His suffering and crucified body of ministry and power, so that we might grow in the Spirit and in the way we love what the Savior has done through the mystery of the Sacraments. It is through the events that occur now that the world is being prepared for the final coming of the Savior, who shall come in full recognition to all people 'on clouds' to raise the living and the dead to their respective judgement.

With this understanding in place, one can still question why so many free willed people that Christ crossed paths with did not know Him to be the Messiah, if He indeed was the Messiah, and to answer such a question requires a brief explanation of grace. The only way in which truth of any kind is revealed to any soul is through the will of God. If God wills that we not know a certain truth, it is fully within His capacity to hide such knowledge from people. This, however, does not eradicate nor interfere with free will, for what comes to pass is still essentially through the reality of our free interaction. So it is that prophecies are secured to pass in the way that they do. Christ's purpose for coming was not to be glorified, but rather to be ridiculed, and as such, He was left with the task of avoiding glorification and renown recognition. Thus, Christ encouraged others not to speak of Him as the Son of God:

Matthew 8:4

And Jesus said to him, "See that you tell no one; but go, show yourself to the priest and present the offering that Moses commanded, as a testimony to them."

Mark 1:34

Jesus healed many who had various diseases. He also drove out many demons, but he would not let the demons speak because they knew who he was.

Matthew 16: 20

Then he warned his disciples not to tell anyone that he was the Christ.

We as a human race did not collectively recognize Christ because it was not in God's will for us to glorify Him. His purpose in the first coming was not to be glorified by all, but to die humbly in submission to the Father for our sins.

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