Daniel 9 is one of the prophecies I have been studying in depth in the past week or so.
To start off, the math doesn't work, no matter what decree you start counting from. Some Christians try to make the math work by inventing something called a "prophetic year" of 360 days in length, but nowhere in the Hebrew Bible is there any such concept. It seems an obvious ploy designed to fit this ONE prophecy! That's circular reasoning.
Also, the Hebrew of Daniel 9 uses a word meaning "cut off" that the Bible ONLY uses for evil persons, not the righteous. Are Christians prepared to admit Jesus was evil? If not, the he was not the one to be "cut off" in the prophecy.
The quote is a poor translation of Daniel, and that poor translation allows Christians to play fast and loose with the supposed fulfillment. In fact, there are several errors in the translation.
For example...
The translation has vs. 25 reading, "Know and understand this: From the issuing of the decree to restore and rebuild Jerusalem until the Anointed One, the ruler,..." This is a mistranslation, since the letter hey that is used to mean "the" is not used in reference to that anointed one, and certainly not twice.
Jesus was never a ruler over anyone. Moreover, Jesus was never anointed, so he could not be the person Daniel was speaking about.
Hebrew doesn't use capital letters, so having the verse read, "the Anointed One," is a blatant and disingenuous attempt to indicate Jesus when that is not necessarily the case.
The verse is mistranslated as far as punctuation, making it to say, "there will be seven 'sevens,' and sixty-two 'sevens.'" No language on Earth says "sixty-nine" that way. The verse should actually read, "Know and discern that from the going forth of the word to restore and build Jerusalem unto one anointed, a prince, shall be seven weeks; and for sixty two weeks shall it be built again with streets and moats, but in troublesome times." Note the main difference -- not that it will take 69 weeks before the messiah will come, but rather a mere 7 weeks. If you study this in the original Hebrew, this should be quite clear. Thus, the translation by itself answers the above question of why not simply write 69, instead of 7 plus 62.
Next, notice that Daniel speaks of TWO anointed ones, one who comes after seven weeks, and the other who is cut off after 62 weeks. If (as Jews agree) these weeks are actually weeks of years, then those two references could NOT be references to the same anointed one.
According to the simple, untwisted translation of verse 26, two events were to occur after the 62 weeks: the anointed one would be cut off, and the city and the sanctuary would be destroyed. As you know, Jerusalem was destroyed in 70 A.D., which is 38 years after the death of Jesus -- more than five "weeks" off. That means Jesus was NOT the anointed one who would be cut off.
I could say more, but for a final point, let me point out that the Christians shuffled the books of the Hebrew Bible, moving Ezra from behind Daniel (where it can be found in a Jewish Bible) to hide the fact that Ezra answered the question of which decree Daniel was worried about that caused the angel to come to Daniel to "make him understand."
Daniel - Chapter 9:1. In the first year of Darius, the son of Ahasuerus of the seed of Media, who was crowned over the kingdom of the Chaldeans. 2. In the first year of his reign, I, Daniel, contemplated the calculations, the number of the years that the word of the Lord had come to Jeremiah the prophet, since the destruction of Jerusalem seventy years. 3. And I turned my face to the Lord God to beg with prayer and supplications, with fasting and sackcloth and ashes.
[...]
21. While I was still speaking in prayer, the man Gabriel, whom I saw in the vision at first, approached me in swift flight about the time of the evening offering. 22. And he enabled me to understand, and he spoke with me, and he said, "Daniel, now I have come forth to make you skillful in understanding.
[...]
24. Seventy weeks [of years] have been decreed upon your people and upon the city of your Sanctuary to terminate the transgression and to end sin, and to expiate iniquity, and to bring eternal righteousness, and to seal up vision and prophet, and to anoint the Holy of Holies.
Here are the verses in Jeremiah Daniel was worked up over:
Jeremiah 25:12. And it shall be at the completion of seventy years, I will visit upon the king of Babylon and upon that nation, says the Lord, their iniquity, and upon the land of the Chaldeans, and I will make it for everlasting desolations.
And
Jeremiah 29:10 prophesied: "For at the completion of seventy years of Babylon I will remember you."
Daniel was concerned. Jeremiah was told that after 70 years from the destruction of Jerusalem, Babylon would be overthrown and the Temple would be rebuilt. Daniel was reading that prediction at the year before the Temple was to be rebuilt, and yet no Jews were even in the Holy Land, much less were any making any effort to rebuild the Temple. There is a verse in the Torah (one of the Five Books of Moses), that says that if Israel doesn't repent, then God will multiply their punishment. Daniel was worried that the Babylonian exile was going to be extended and on an order of seven times longer than Jeremiah had been told. Daniel then prayed to God in sackcloth and with great mourning. The angel Gabriel came to Daniel with an answer from God. Gabriel told Daniel that he was counting from the wrong starting point, and that the Temple would indeed be rebuilt on schedule.
Now see Ezra.
Ezra - Chapter 1:1. And in the first year of Cyrus, the king of Persia, at the completion of the word of the Lord from the mouth of Jeremiah, the Lord aroused the Spirit of Cyrus, the king of Persia, and he issued a proclamation throughout his kingdom, and also in writing, saying: 2. "So said Cyrus, the king of Persia, 'All the kingdoms of the earth the Lord God of the heavens delivered to me, and He commanded me to build Him a House in Jerusalem, which is in Judea. 3. Who is among you of all His people, may his God be with him, and he may ascend to Jerusalem, which is in Judea, and let him build the House of the Lord, God of Israel; He is the God Who is in Jerusalem. 4. And whoever remains from all the places where he sojourns, the people of his place shall help him with silver and with gold and with possessions and with cattle, with the donation to the House of God, which is in Jerusalem.'
This verse tells of the fulfillment of Jeremiah's prophecy.