Does Daniel 9:25 say that the Messiah should come before the destruction of the second temple as some claim? I find that verse hard to comprehend. If yes, then could we directly show this verse to the Jews and make them believe that Jesus indeed was the Messiah?
I believe that Daniel 9:24-27 is unambiguously a prophecy, both about the coming of the Messiah to Jerusalem and of the subsequent destruction of Jerusalem by the Romans. In verse 24 it describes a time when the “Anointed One” (messiah in Hebrew) will come to Jerusalem to “finish transgression, to put an end to sin, to atone for wickedness, to bring in everlasting righteousness” and to “seal up vision and prophecy.” What else could this be about? If there ever was a clear-cut messianic prophecy it is this one. The only way to avoid this conclusion is to either deny that the Old Testament predicts the coming of a Messiah or to choose ahead of time to ignore any evidence which points toward Jesus of Nazareth as the Messiah.
Then there is Daniel 9:26, which describes the coming of a ruler to Jerusalem. This ruler will destroy Jerusalem and the temple. He will establish the Abomination of Desolation in the sanctuary. If this is not about the destruction of Jerusalem under Titus in AD 70, then what might it be about? I suppose it could just possibly be about the second destruction of Jerusalem after the bar Kochba rebellion (AD 132-135), but the rebellion did not result in the destruction of the temple of in an abomination of Desolation. Here is the bottom line on this: any reasonable and open-minded person who believes that prophecy is a possibility will conclude that Daniel 9:25-27 is about the destruction of Jerusalem by Roman emperor Titus in AD 70.
Therefore, it seems inescapable that Daniel 9:24-27 is a prophecy of the coming of the Messiah at a time shortly before the destruction of Jerusalem by the Romans. The amount of time between the coming of the Messiah and the destruction of Jerusalem is not clear in this prophecy. Of course, we know that Jesus told his followers that within the lifetime of the apostles, Jerusalem would be destroyed and the Abomination of Desolation would be established on the temple mount. He even tells us that this coming destruction is the same as that prophesied by Daniel. All this is in Matthew 24:15-21.
Of course, a Jewish person might not be willing to listen to what Jesus prophesied concerning the destruction of Jerusalem and his claim that this is the same as what was prophesied by Daniel. They may simply refuse to listen to anything the pretender Jesus of Nazareth says, and that is their choice. Matthew is not part of their scripture. However, any open-minded Jew surely would agree that Daniel 9:24-27 is a messianic prophecy, and the relationship to the destruction of Jerusalem is hard to miss. Perhaps this would be sufficient to get a reasonable Jewish person to at least look at the prophecy of Jesus as recorded in Matthew before the events of AD 70. Hopefully a reasonable open-minded person, even if they were trained to think differently, would be open to seeing the obvious. So I say go ahead and give it a try.