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:
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.