I think the text actually states "with THE many"… which often in Scripture elsewhere the phrase "
the many" is referring to Israel.
In my own studies, I came to the following conclusion long before I read any commentaries on it, but I happen to like how William Kelly says it
:
[quoting Wm Kelly on Dan9:25]
"Then,
in verse 25, the first particular comes in, after defining the starting-point. "Know therefore and understand, that
from the going forth of the commandment
to restore [H7725] and to build [H1129] Jerusalem,
unto the Messiah the Prince, shall be seven weeks, and threescore and two weeks." Now, in the Book of Ezra, we have a commandment from the king Artaxerxes, called in profane history Artaxerxes Longimanus, one of the monarchs of the Persian Empire.
The first commandment was given to Ezra, the scribe, "in the seventh year of Artaxerxes the king." In the twentieth year of the same monarch's reign,
another commandment was given to Nehemiah.
Now it is important for us to decide which of these two is referred to by Daniel. The earlier of them is recorded in Ezra 7, the second in Nehemiah 2. A careful examination of the two will show which is meant. Many excellent persons have interpreted it in a way which differs from that which I believe to be correct.
But Scripture alone can decide the questions that arise out of Scripture. Foreign elements often lead to perplexity.
Remark, that it is not merely a general order to the Jews, like that of Cyrus permitting their return, but a special one to restore their polity. Now, what is the difference between the two in the reign of Artaxerxes?
The one to Ezra was mainly with a view to the rebuilding of the temple; the other to Nehemiah looks toward the city. Which is it here? "Know therefore and understand, that from the going forth of the commandment
to restore and to build Jerusalem." Evidently
the city is intended in Daniel;
and if so, then we must see which of the two commandments concerns the city. There can be little doubt
it was the second, not the first. It was the commission given to Nehemiah in the twentieth year of Artaxerxes, not that to Ezra thirteen years before. A comparison with Nehemiah will confirm this."
--William Kelly, Commentary on Daniel 9 [source: Bible Hub; bold and underline mine, bracketed inserts mine]
[end quoting]
This was fulfilled on [what we call] Palm Sunday, when Jesus said what He did in Luke 19:41-44 [
re: 'the city'] and did what He did [
fulfilling Zech9:9, also regarding 'the city' ('THY King cometh UNTO THEE'--speaking to 'Jerusalem')].
The Subject of the prophecy in Dan9:24 is indeed stated to be "[70 Wks are determined upon]...
and upon thy [Daniel's] holy city"