Sarah,
Firstly, I say that Daniel 9 has no relevance to Jesus.
Some say that one person being referred to is Onias (search the www). But as you noted, there are two people being referred to in these verses. I do not offhand recall the name of the other High Priest who is suggested as the other person.
Remember that "Anointing" referred to the smearing of oil on the High Priest. The Hebrew word is Mesach (Messiah) the Greek is Christ. So the priest was the Anointed One (namely, the "Messiah" or the "Christ"). - Many will come in my name (authority) and say I am the Christ (the Anointed - think of the WTS's GB).
Before I proceed, let me give you another curly one to consider: why did Jesus speak of the "Son of Man" who is coming as being a person who was different from him? ("When the Son of Man comes he will ...". It is as if Jesus was intending to set himself up as "The King of the (imminent) Kingdom" that this Son of Man was about to instigate. The Romans said that he intended to make himself king of the Jews, (hence his triumphal ride into Jerusalem) which in the Romans' eyes was the height of insurrection.
I apologise for making it difficult for you, so here are the relevant verses that I put up:
Doug
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Daniel 9:24-27
Tanach, The Stone Edition (MT):
Daniel 9:24 Seventy septets have been decreed upon your people and upon your holy city to terminate transgression, to end sin, to wipe away iniquity, to bring everlasting righteousness, to confirm the visions and prophets, and to anoint the Holy of Holies. 25 Know and comprehend: From the emergence of the word to return and to build Jerusalem until the anointment of the prince will be seven septets, and for sixty-two septets it will be rebuilt, street and moat, but in troubled times. 26 Then, after the sixty-two septets, the anointed one will be cut off and will exist no longer; the people of the prince will come will destroy the city and the Sanctuary; but his end will be [to be swept away as] in a flood. Then, until the end of the war, desolation is decreed. 27 He will forge a strong covenant with the great ones for one septet; but for half of that septet he will abolish sacrifice and meal-offering, and the mute abominations will be upon soaring heights, until extermination as decreed will pour down upon the mute [abomination].
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New JPS Translations (MT):
24”Seventy weeks have been decreed for your people and your holy city until the measure of transgression is filled and that of sin complete, until iniquity is expiated, and eternal righteousness ushered in; and prophetic vision ratified, and the Holy of Holies anointed. 25You must know and understand: From the issuance of the word to restore and rebuild Jerusalem until the [time of the] anointed leader is seven weeks; and for sixty-two weeks it will be rebuilt, square and moat, but in a time of distress. 26And alter those sixty-two weeks, the anointed one will disappear and vanish. The army of a leader who is to come will destroy the city and the sanctuary, but its end will come through a flood. Desolation is decreed until the end of war. 27During one week he will make a firm covenant with many. For half a week he will put a stop to the sacrifice and the meal offering. At the corner [of the altar] will be an appalling abomination until the decreed destruction will be poured down upon the appalling thing.”
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The Septuagint (Brenton):
24 Seventy weeks have been determined upon thy people and upon the holy city for sin to be ended, and to seal up transgressions, and to blot out the iniquities, and to make atonement for iniquities, and to bring in everlasting righteousness, and to seal the vision and the prophet, and to anoint the Most Holy.
25 And thou shalt know and understand, that from the going forth of the command for the answer and for the building of Jerusalem until Christ the prince there shall be seven weeks, and sixty-two weeks: and then the time shall return, and the street shall be built, and the wall, and the times shall be exhausted.
26 And after the sixty-two weeks, the anointed one shall be destroyed, and there is no judgment in him: and he shall destroy the city and the sanctuary with the prince that is coming: they shall be cut off with a flood, and to the end of the war which is rapidly completed he shall appoint the city to desolations. 27 And one week shall establish the covenant with many: and in the midst of the week my sacrifice and drink-offering shall be taken away: and on the temple shall be the abomination of desolations ; and at the end of the time an end shall be put to the desolation.