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The year in view was 711 B.C. Like Isaiah 7:1, Isaiah 20:1 introduces the historical setting for the events that follow. For four years, Egypt had encouraged the city-states of western Palestine to resist Assyrian aggression-with the promise of assistance. In 713 B.C., Ashdod, the northernmost Philistine town that stood about 35 miles west of Jerusalem, had rebelled, and Assyria replaced her king, Ahimiti (Azuri), with another, a man named Yamani (Jaman). Rebellion continued, however, and pleas for help went out from Ashdod to Judah, Moab, and Edom. Sargon II (722-705 B.C.) responded to Ashdod’s rebellion by sending his second in command, who reduced Ashdod to an Assyrian province. Egypt’s promised help never materialized. In fact, the Egyptians handed Yamani over to the Assyrians in chains to avoid an Assyrian attack.
During that period, God instructed His prophet to dramatize a message. Jeremiah and Ezekiel often dramatized prophecies, but this is the only time Isaiah did as far as the text records. Isaiah was to take his clothes off, including his shoes. The word "naked" (Heb. ’arom) can mean: clothed only with a loin cloth, or totally naked (cf. Isaiah 58:7; Genesis 2:25; 1 Samuel 19:24; 2 Samuel 6:20; Micah 1:8; John 21:7). If God wanted Isaiah to go totally naked He probably would not have mentioned his shoes. Isaiah may have been wearing sackcloth because he was mourning (cf. Isaiah 15:3), but this may have been his normal garment (cf. 2 Kings 1:8).
"With the great importance attached to the clothing in the East, where the feelings upon this point are peculiarly sensitive and modest, a person was looked upon as stripped and naked if he had only taken off his upper garment. What Isaiah was directed to do, therefore, was simply opposed to common custom, and not to moral decency. He was to lay aside the dress of a mourner and preacher of repentance, and to have nothing on but his tunic (cetoneth); and in this, as well as barefooted, he was to show himself in public. This was the costume of a man who had been robbed and disgraced, or else of a beggar or prisoner of war." [Note: Delitzsch, 1:372.]
For three years, Isaiah appeared in public as God had instructed him, to portray the condition of the Egyptian and Cushite captives that the Assyrians would take in reprisal for stirring up trouble. A Cushite dynasty was in power in Egypt at this time, which accounts for the prominence of Cush in this prophecy. During those three years, Isaiah’s observers doubtless concluded that his condition represented the fate of the people of Ashdod. At the end of three years, God told Isaiah to explain the significance of his strange behavior. That he had portrayed the Egyptians and Cushites, and not the people of Ashdod, would have shocked the Judeans, because many of them favored relying on Egypt and Cush for protection against Assyria. Isaiah’s prophecy was fulfilled in 701 B.C. when the Assyrians defeated Egypt at Eltekeh. Another less likely possibility, I think, is Esarhaddon’s conquest of Egypt in 671 B.C.
Isaiah predicted the dismay of the pro-Egyptian faction in Judah when Assyria carried the Egyptians and Cushites off as captives. This happened in 701 B.C. The Judeans had hoped that they would get help from the Egyptians and Cushites against the Assyrians, but now how could they escape? The obvious though unstated answer is, Trust in the Lord, not Egypt!
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Constable, Thomas. DD. "Commentary on Isaiah 20". "Dr. Constable's Expository Notes". https://www.studylight.org/
the Third Sunday after Epiphany