"Ravshakeh then told them, Go tell Chizkiyahu (Hezekiah) that this is what the great king, the king os Assyria says: "what is it that makes you so confident?" - Isaiah 36:4
Not even referring to Chizkiyahu as king, Ravshakeh, shows his low opinion of him. The king of Assyria is the "great one," because of his mighty armies and vast kingdom. Who is Chizkiyahu? - just king of Jerusalem and even that shall be taken from him, or rather, he shall be taken captive from it. And what makes Chizkiyahu so confident that he sends out Temple servants, rather than army generals?
"You said, 'It is only words, 'but strategy and strength (are needed) in war. On whom, then, do you trust, that you have rebelled against me?" - Isaiah 36:5
Arguing that strategy and strength are needed in war, Ravshakeh mocks Chizkiyahu who said that victory is "only a matter of words" - of prayer. He also alludes to him that his rebellion is only empty words, as long as he has yet to face war. But Ravshakeh also accused Chizkiyahu of beguiling words when he promised to give tribute to Assyria - it was only a scheme to bid for time in order to gain strategy and strength for war.
"And if you say to me, "We trust in our Lord, G-d, 'but was it not He Whose shrines and altars Chizkiyahu removed, telling Yehudah and Jerusalem, 'Prostrate only before this altar?'" - Isaiah 36:7
And if Chizkiyahu's trust be upon G-d, this too, will prove futile, argues Ravshakeh: Had not Chizkiyahu abolished the Judeans' private altars to force them to bring their offerings to the Temple? Why did he do this, if not for his own honor? Why, then, should G-d help him? (This argument was, of course, only Ravshakeh's false opinion, because altars to G-d are forbidden outside the Temple.
"So wager now with my master, the king of Assyria: I shall give you two thousand horses - can you provide riders for them? So how, then, can you confront even one officer of my master's lesser servants and rely on Egypt for chariots and riders?" - Isaiah 36:8-9
So if it is futile for Chizkiyahu to trust G-d or Egypt, interjects Ravshakeh, he must trust Yehudah's own strength. But this, too, he argues, is useless - Chizkiyahu does not even have an army of two thousand horsemen. The smallest unit, however, of Sancheiriv's cavalry consists of two thousand riders and there are one hundred and eighty-five thousand such units - how can you hope to match them? So what use would it be to seek help from Egypt when you yourselves have no army basis?
"And now, is it without G-d that I have come against this Land to destroy it? - G-d has told me, 'Go up to this Land and destroy it!'" - Isaiah 36:10
And even if Chizkiyahu had fulfilled G-d's will by destroying the private altars, Ravshakeh concludes Sancheiriv's words, it was G-d who bade to destroy this country (words of Isaiah's public prophecies about it (above 8:6-7) had reached faraway Assyria).
"Elyakim, Shevna, and Yoach then said to Ravshakeh: "Please speak to your servants in Aramaic - we understand it - and don't speak to us in Hebrew in front of the people on the wall." - Isaiah 36:11
Ravshakeh, all along, had been speaking in his native Hebrew - he was a Jewish apostate. He did this intentionally to frighten the masses "on the wall," but Elyakim, Shevna and Yoach perhaps did not realize this and asked him not to panic the people. And if they did realize, they hid their intentions arguing that Aramaic would serve him better: Hebrew would underscore his Jewishness, leading the people to rely on having a "brother" in the Assyrian palace. They further were disturbed by Ravshakeh's blasphemies and did not want the masses to hear them.
"Ravshakeh answered: "Was it to you and to your master that my master sent me to speak these words? Was it not specifically to the people sitting on the wall, that they will eat their excrement and drink their own urine - together with you!"- Isaiah 36:12
"Ravshakeh stood up and called out in a loud voice, in Hebrew, saying: Hear the words of the great king, the king of Assyria! Thus says the king: "Do not let Chizkiyahu fool you - he cannot save you! Let not Chizkiyahu reassure you in G-d, by saying, 'G-d shall surely save us and this city shall not fall into the hands of the king of Assyria.'" - Isaiah 36:13-15
Ravshakeh stood up, as it to honor them, but he really meant just to fool them into thinking that he sought their welfare. Chizkiyahu cannot protect you, he said, whether through human effort or with G-d's help. Better to surrender now, rather than suffer starvation.
"Do not listen to Chizkiyahu, for thus says the king of Assyria: "Make peaceful tribute and come out to me. Each person will eat from his own vine and his own fig tree and each one will drink from his own well - until I will come and bring you to a land like your Land, a land of grain and wine, a land of bread and vineyards." - Isaiah 36:16-17
Ravshakeh urges them to surrender themselves in order to avoid annihilation - that way they will be able to leave the city and eat from the fruit of their fields. But even surrrender would only save them their lives, they they would not be allowed to stay in the Land. (To assure that the conquered nations would not rebel, the Assyrians transported from from one place to another.) Nevertheless, he promises to bring them to a land as nice as their own. This, to persuade them to surrender.
"And lest Chizkiyahu lure you by saying, 'G-d will save us,' did any of the gods save his land from the king of Assyria? Where were the gods of Hamat and Arpad, where were the gods of Sefarvayim? Did they save Shomron from me? Were there any of all the lands' gods which saved their lands from me, that G-d should save Jerusalem from me?"- Isaiah 36:18-20
Comparing the Infinite G-d to man made images, Ravshakeh argues that not even G-d can save them. G-d did not save Shomron from the Assyrians as did not the gods which they worshiped, the gods of Hamat, et al.
"They remained silent and answered him nothing, for the king's order was, "Do not answer him," Elyakim son of Hilkiyah, who was in charge of the palace, Shevna the scribe and Yoach son of Asaf the secretary, came in front of Chizkiyahu with rent clothes and told him what Ravshakeh said." - Isaiah 36:21-22
Pained by the blasphemies of Ravshakeh, the three sages rent their clothes. Nevertheless, they did not refute him and followed Chizkiyahu's instructions. When one is disgraced, one should not retort, but leave G-d to carry out judgment.
Commentary by Meam Loez