Did Isaiah’s prophecy that Damascus would cease being a city fail?

Answer:

"Then I went to the prophetess, and she conceived and bore a son. Then the LORD said to me, "Call his name Maher-Shalal-Hash-Baz; for before the child shall have knowledge to cry 'My father' and 'My mother,' the riches of Damascus and the spoil of Samaria will be taken away before the king of Assyria" (Isaiah 8:3-4).

"The burden against Damascus. "Behold, Damascus will cease from being a city, and it will be a ruinous heap"" (Isaiah 17:1).

""But I will send a fire into the house of Hazael, which shall devour the palaces of Ben-Hadad. I will also break the gate bar of Damascus, and cut off the inhabitant from the Valley of Aven, and the one who holds the scepter from Beth Eden. The people of Syria shall go captive to Kir," says the LORD" (Amos 1:4-5).

"Under Rezin (Assyr. Rahianu) Aram again oppressed Judah (2 Ki. 16:6), and in 738 was, with Menahem of Israel, a vassal of Tiglath-pileser III of Assyria. Soon thereafter Rezin revolted, captured Elath and took many Judaens captive to Damascus (2 Chr. 28:5). Ahaz of Judah thereupon appealed for help to Assyria who responded by launching a series of punitive raids in 734-732 BC, which cumulated in the capture of Damascus, as prophesied by Isaiah (17:1) and Amos (1:4-5), and the death of Rezin." ["Damascus," The Illustrated Bible Dictionary, Tyndale, Vol. I, p. 357].

Tiglath-pileser conquered Damascus during the fourth year of King Ahaz's reign. "So the king of Assyria heeded him; for the king of Assyria went up against Damascus and took it, carried its people captive to Kir, and killed Rezin. Now King Ahaz went to Damascus to meet Tiglath-Pileser king of Assyria ..." (II Kings 16:9-10).

It was during the early years of Hezekiah that Assyria once again swept down and captured the northern kingdom of Israel, whose capital was Samaria. "And at the end of three years they took it. In the sixth year of Hezekiah, that is, the ninth year of Hoshea king of Israel, Samaria was taken. Then the king of Assyria carried Israel away captive to Assyria, and put them in Halah and by the Habor, the River of Gozan, and in the cities of the Medes" (II Kings 18:10-11). To get to Israel, Damascus would have also been overrun. The Assyrians practiced a technique of destroying everything they conquered so there could be no enemy forces behind their advancing lines. The Assyrians were stopped by God before they destroyed Jerusalem and they retreated from there.

Another prophecy is against Damascus in Jeremiah: "Against Damascus. "Hamath and Arpad are shamed, for they have heard bad news. They are fainthearted; there is trouble on the sea; it cannot be quiet. Damascus has grown feeble; she turns to flee, and fear has seized her. Anguish and sorrows have taken her like a woman in labor. ... I will kindle a fire in the wall of Damascus, and it shall consume the palaces of Ben-Hadad" " (Jeremiah 49:23-24, 29). See also Zechariah 9:1.

Babylon, under King Nebuchadnezzar, destroyed Assyria and then made its way south. It destroyed Jerusalem and reached all the way to Egypt. "In 572, all of Syria had been conquered by the Neo-Babylonians, but the status of Damascus under Babylon is relatively unknown" [Wikipedia, citing Ross Burns, Damascus: A History, 2005]. It then was conquered by Alexander the Great and then later by the Romans.

Each time Damascus was destroyed, it was rebuilt. Notice that the prophecies against Damascus never said that the destruction was permanent. It went through short periods of non-existence, only to be later resurrected. Some of the things I noticed while researching this were statements like, "Demetrius III Philopator rebuilt the city according to the Greek Hippodamian system" and "The city of Damascus was entirely redesigned by the Romans after Pompey conquered the region." The implication is that the city was destroyed and then rebuilt on models of the conquerors.