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The word Hosanna has many meanings: "help", "save, I pray", "Save, now!" or Praising etc.

If the people shouted "Hosanna" in order to praise Jesus merely as a great Prophet, it would be easier to shout "Crucify him!" later when they were disappointed by his acts.

If the intention of the people of Jerusalem was to say "Save us from the hands of Rome", it means they accepted Jesus as the Messiah after seeing all the miracles he performed. But in less than a week they became impatient and shouted "Crucify him!", thereby rushing to a conclusion that Jesus was actually not the Messiah.

What was the intention of the people of Jerusalem when they shouted Hosanna?

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I think you may have answered your own question. I think they intended him to save them from Rome, specifically, and reestablish the sovereignty of the Jewish Nation. He didn't do that, and so they then saw no use for him. –  David Morton Apr 3 '13 at 14:07
    
@DavidMorton - I think this is a good question, and while Mawia has the start of a good answer, it needs more –  warren Apr 3 '13 at 14:24
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@warren Exactly. This is all I can come up with. It needs more Biblical and Historical background to explain it clearly. –  Mawia Apr 3 '13 at 15:08
    
It should also be noted that "Hosanna" seems to be coming from the people who came with Jesus not the people of Jerusalem (e.g., Matt.21:10-11 has the city asking "Who is this?" and the crowds responding "Jesus, the prophet from Nazareth in Galilee". People in Jerusalem would be more sensitive to political repercussions and likely more aligned with the religious leadership (Caiaphas' advice in John 11:50 would be more compelling) compared to Jesus' followers. "Crucify him!" may have come from the people of Jerusalem (rf. Luke 19:41-44). –  Paul A. Clayton Apr 3 '13 at 16:34

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Many of the people of Jerusalem indeed thought that Jesus was the Messiah. There were so many prophecies that were fulfilled by Jesus, and the common person at least had knowledge of some of these prophecies, as they were what many of them had to look forward to.

On Palm Sunday, Jesus fulfilled one more prophecy (Zechariah 9:9) that many would not have missed:

Rejoice greatly, O daughter of Zion!

Shout in triumph, O daughter of Jerusalem!

Behold, your king is coming to you;

He is just and endowed with salvation,

Humble, and mounted on a donkey,

Even on a colt, the foal of a donkey.

When the Jewish people shouted "Hosanna", regardless of which specific meaning the word had, the intent of the people was clear. They wanted a political or military Messiah, not a religious one. They wanted an earthly King.The article here goes into this in a little more detail, but in summary:

[There was a] switch in public opinion. At the Triumphal Entry, Jerusalem rejoiced. But then Jesus failed their expectations. He had come to defeat sin and death, not Rome. His kingdom was in hearts, not on a throne (at least not yet). They began to reject Jesus as the campaign of lies by the religious leaders had its effect. Finally, by the time Jesus stood before Pilate, there had been a dramatic shift in public opinion.

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Jesus's entrance on a donkey, while it did fulfill this prophecy, was hardly a unique enough event that people "would not have missed" it. It was a common means of transportation, as well as being a standard piece of symbolism, showing a king arriving in peace, as opposed to riding on a horse (a beast of war) as a conqueror. –  Mason Wheeler Apr 3 '13 at 17:18
    
That's not entirely true... Jews do not accept Jesus as the messiah because: Jesus did not fulfill the messianic prophecies. Jesus did not embody the personal qualifications of the Messiah. Biblical verses "referring" to Jesus are mistranslations. Jewish belief is based on national revelation. aish.com/jw/s/48892792.html To say that Jesus fulfilled the prophecies that Jewish people expected is not exactly true. –  The Freemason Apr 3 '13 at 17:52
    
Not all of them, no. But they recognized some of them, and they were looking for him to fulfill the prophecies in the way that they wanted. –  SSumner Apr 3 '13 at 18:27

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