I struggle when I see learned theologians affirming the Messiah or a Messiah is the one making a covenant in verse 27. It seems it is just the eagerness to debunk a key factor for those who embrace dispensationalism.
Daniel 9:26-27
And after the sixty-two weeks, an anointed one shall be cut off and shall have nothing. And the people of the prince who is to come shall destroy the city and the sanctuary. Its end shall come with a flood, and to the end there shall be war. Desolations are decreed. 27 And he shall make a strong covenant with many for one week, and for half of the week he shall put an end to sacrifice and offering. And on the wing of abominations shall come one who makes desolate, until the decreed end is poured out on the desolator.” ESV
By basic grammar rules, the antecedent of the pronoun He is the prince of the people.
The CEV and the NLT already translate in order to make the antecedent understood. Many people mock these versions, but these are translated by scholars, they may chop the beauty and literality, but regarding grammar those are very useful.
26 “After this period of sixty-two sets of seven, the Anointed One will be killed, appearing to have accomplished nothing, and a ruler will arise whose armies will destroy the city and the Temple. The end will come with a flood, and war and its miseries are decreed from that time to the very end. 27 The ruler will make a treaty with the people for a period of one set of seven, but after half this time, he will put an end to the sacrifices and offerings. And as a climax to all his terrible deeds, he will set up a sacrilegious object that causes desecration, until the fate decreed for this defiler is finally poured out on him.” NLT
At the end of the 62 weeks, the Chosen Leader will be killed and left with nothing.A foreign ruler and his army will sweep down like a mighty flood, leaving both the city and the temple in ruins, and war and destruction will continue until the end, just as God has decided. 27 For one week this foreigner will make a firm agreement with many people, and halfway through this week, he will end all sacrifices and offerings. Then the “Horrible Thing” that causes destruction will be put there. And it will stay there until the time God has decided to destroy this one who destroys CEV
In Hebrew neither Ruler, People or Messiah have any definite article, the three of them are in masculine and singular grammatically. Keeping in mind that the Messiah already is dead in verse 26, the only possible option is the Ruler or the Ruler with the people.
Are there any possible sound hermeneutics by which the ( or a) Messiah is the one making the covenant in Dan 9:27?