Deuteronomy 28:52 - Joseph Benson’s Commentary on the Old and New Testaments

He shall besiege thee in all thy gates Thus did Shalmaneser, Sennacherib, and Nebuchadnezzar. See 2Ki 18:9-10; 2 Kings 18:13, and 2 Kings 25:10. But this prediction was especially fulfilled by the Romans, to whom the best fortified places in Judea were forced to yield, as may be seen in Josephus's History of the Jewish war, which is the best commentary on this part of the prophecy. And the Jews might well be said to trust in their high and fenced walls; for they seldom ventured to fight in the open field. In particular, they confided in the strength and situation of Jerusalem, as the Jebusites, the former inhabitants of the place, had done before them, 2 Samuel 5:6-7.