What we have is sort of parallelism: The first two clauses in Daniel 9:27 are a continuation of the first clause in the previous verse (Dan. 9:26). And the third (last) clause in Daniel 9:27 is a continuation of the last two clauses in Daniel 9:26.
The first part of Dan. 9:26 says, "And after threescore and two weeks shall Messiah be cut off, but not for himself." This undoubtedly is talking about Jesus Christ. The rest of this verse says, ": and the people of the prince that shall come shall destroy the city and the sanctuary; and the end thereof shall be with a flood, and unto the end of the war desolations are determined." I don't think anybody would argue with these last two clauses (of verse 26) being about Prince Titus. History bears this out.
Going on to Dan. 9:27 we have, "And he shall confirm the covenant with many for one week: and in the midst of the week he shall cause the sacrifice and the oblation to cease." The pronoun "he" does not refer to the nearest noun antecedent; "he" refers to the nearest noun antecedent that is the subject of a clause. In other words the pronoun "he" does not refer to "the prince" from the previous verse; rather it refers back to "Messiah" from the previous verse. That's because "the prince" is not the subject of the clause it is in; "the prince" is a modifier: a descriptive that tells us to whom "the people" belong. The soldiers of Prince Titus stormed Jerusalem in 70 AD, after some three and a half years of laying siege to it. These soldiers destroyed the Chosen City and also razed the Temple, which they were commanded by Titus to not tear down. In their work of slaughter and destruction the Roman soldiers got carried away--employing fire in their endeavor to level the Temple. Afterwards, the gold (which Titus was after) had melted and became stuck between the jumbled mass of stone bricks as it cooled. Titus ordered his men to extract the gold from the Temple ruins. Now you can see that it was "the people" who pillaged Jerusalem. And the descriptive "the prince" tells us whom these soldiers served.
We must then conclude that "he" in Dan. 9:27 is speaking of the Christ. He confirmed (the confirmation lasting 7 years) the New Covenant "with many." The "many" is referring to scattered Israel--most of whom were in Europe. That's why this confirmation ended in 34 AD (having begun in 27 AD). For Jesus confronted Saul when the latter was on his way to Damascus to arrest Christians. Saul became a servant of Christ Jesus from then onwards. God gave Saul--who became Paul--the mission of taking the Gospel to the Israelites of Europe: as John 10:16 says,"And other sheep I have, which are not of this fold: them also I must bring, and they shall hear my voice; and there shall be one fold, and one shepherd." Paul had a great part in helping to begin the fulfillment of those words of Jesus, which were also were prophesied in Jeremiah 37--that the scattered Northern Kingdom of Israel would be reunited with the Judahites (Sephardic Jews). And those Israelites--who sailed away from Egypt before the Exodus under Moses and thus becoming the Achaean Greeks and the Trojans--would also be reunited with the rest of Israel. Christianity spreading throughout Europe is what is meant by "he" confirming the [new] covenant with "many."