Yes, "they failed to connect the prophecy with their reality."The pharisees failed to recognize Yeshua as a suffering servant who must die as an atonement for the sin of mankind. In their deep-rooted paradigm, the messiah, Son of David only comes once as a conquering king to liberate them and build his kingdom, while the nation of Israel is symbolized as a suffering servant. And it was not just the pharisees, but the disciples as well. They never understood that until they witnessed the death, burial and resurrection of the Lord. Simply put, they failed to connect the prophecy with their reality.
If we deeply analyze the events in the light of the Scriptures, we will see that when JESUS came, around 587 years had already passed since the destruction of the kingdom of Judah and the Temple of Jerusalem by Nebuchadnezzar; and part of the prophecies of Daniel chapter 7 had been fulfilled in the first coming of JESUS.
Today, we can accurately discern that with the coming of JESUS, the promised Messiah, a prophetic part of Daniel 9:27 was literally fulfilled. It is easy for us today to interpret the fulfillment of prophecy in this particular verse, because it is a prophecy literally fulfilled, but we cannot say the same for the people and priests, religious leaders, and students of Scripture at that time. John the Apostle wrote: JESUS, the Messiah, came unto His own, and His own received Him not. He was in the world, and the world was made by Him, and the world knew Him not-John 1:10-11.
Isaiah had even prophesied:"He hath no handsome nor comeliness; when we shall see Him, there is no beauty that we should desire Him(his appearance did not attract us). He is despised and rejected of men; a man of sorrows, and acquainted with grief: and we hid as it were our faces from him; he was despised, and we esteemed him not.
Well, as you said "Israel failed to connect the prophecy with their reality." Of the same manner, the generation of Christian believers today also "fails to connect the prophecy with their reality". Why? Because came a falling away and many departed themselves from the faith, giving heed to seducing spirits, and doctrines of devils, this evil spiritual environment opens the door for the appearance of the Dragon-Revelation 13:11, and the man of sin, son of perdition, may manifest himself at any moment from now on.Unfortunately, the same mistake is being made today, prophecy that count for a third of the bible is rarely taught. Some are even drowned in an illusion that Christ has already returned and His kingdom is already built, it's like one of the earliest communist slogan - WE ARE THE MESSIAH WE'VE BEEN WAITING FOR! This is erroneous and dangerous, you know, since the opposite is happening - the Dragon is about to be cast down to earth. We must cling closely to Christ more than ever, He's our only hope. To be honest, I used to believe Trump was until Jan 6.
Regarding Mr. Trump I think he may be the horserider of the red horse, and an allied of the future and religious Man Beast, the red Dragon, a religious MONSTER of seven heads, and ten horns, and seven crowns upon his heads -Revelation 12:3-4 - , and a powerful TAIL - Isaiah 9:15-16.
There will be a battle against the red Dragon, he must be laid hold; the old serpent, which is the Devil, and Satan, he must be cast into the bottomless pit, and shut him up, and set a seal upon him, that he should deceive the nations no more.
But who is prepared for this battle? By the way, if the trumpet give an uncertain sound, who shall prepare himself to the battle?
May our Lord GOD bless and keep us, and give us His protection. Amen