In the fourteenth year of King Hezekiah, Sennacherib king of Assyria came up against all the fortified cities of Judah and took them. 2 And the king of Assyria sent the Rabshakeh from Lachish to King Hezekiah at Jerusalem, with a great army. And he stood by the conduit of the upper pool on the highway to the Washer's Field. 3 And there came out to him Eliakim the son of Hilkiah, who was over the household, and Shebna the secretary, and Joah the son of Asaph, the recorder.
4 And the Rabshakeh said to them, “Say to Hezekiah, ‘Thus says the great king, the king of Assyria: On what do you rest this trust of yours? 5 Do you think that mere words are strategy and power for war? In whom do you now trust, that you have rebelled against me? 6 Behold, you are trusting in Egypt, that broken reed of a staff, which will pierce the hand of any man who leans on it. Such is Pharaoh king of Egypt to all who trust in him. 7 But if you say to me, “We trust in the Lord our God,” is it not he whose high places and altars Hezekiah has removed, saying to Judah and to Jerusalem, “You shall worship before this altar”? 8 Come now, make a wager with my master the king of Assyria: I will give you two thousand horses, if you are able on your part to set riders on them. 9 How then can you repulse a single captain among the least of my master's servants, when you trust in Egypt for chariots and for horsemen? 10 Moreover, is it without the Lord that I have come up against this land to destroy it? The Lord said to me, “Go up against this land and destroy it.”’”
11 Then Eliakim, Shebna, and Joah said to the Rabshakeh, “Please speak to your servants in Aramaic, for we understand it. Do not speak to us in the language of Judah within the hearing of the people who are on the wall.” 12 But the Rabshakeh said, “Has my master sent me to speak these words to your master and to you, and not to the men sitting on the wall, who are doomed with you to eat their own dung and drink their own urine?”
13 Then the Rabshakeh stood and called out in a loud voice in the language of Judah: “Hear the words of the great king, the king of Assyria! 14 Thus says the king: ‘Do not let Hezekiah deceive you, for he will not be able to deliver you. 15 Do not let Hezekiah make you trust in the Lord by saying, “The Lord will surely deliver us. This city will not be given into the hand of the king of Assyria.” 16 Do not listen to Hezekiah. For thus says the king of Assyria: Make your peace with me and come out to me. Then each one of you will eat of his own vine, and each one of his own fig tree, and each one of you will drink the water of his own cistern, 17 until I come and take you away to a land like your own land, a land of grain and wine, a land of bread and vineyards. 18 Beware lest Hezekiah mislead you by saying, “The Lord will deliver us.” Has any of the gods of the nations delivered his land out of the hand of the king of Assyria? 19 Where are the gods of Hamath and Arpad? Where are the gods of Sepharvaim? Have they delivered Samaria out of my hand? 20 Who among all the gods of these lands have delivered their lands out of my hand, that the Lord should deliver Jerusalem out of my hand?’”
21 But they were silent and answered him not a word, for the king's command was, “Do not answer him.” 22 Then Eliakim the son of Hilkiah, who was over the household, and Shebna the secretary, and Joah the son of Asaph, the recorder, came to Hezekiah with their clothes torn, and told him the words of the Rabshakeh. Isaiah 36 ESV
Isaiah 36 Sennacherib threatens to invade Jerusalem
1-3. In the 14 year of Hezekiah - The links above will give more the setting to this. Jerusalem is in Judah, and the fortified cities have already been taken by the Assyrian army. This is what Isaiah had already prophesied was coming.
Eliakim, Shebna and Joah - These would be members of Hezekiah's cabinet, men he held close to him.
4-10. And the Rabshakeh - The high ranking officer (field commander) of Sennacherib, king of Assyria. He was sent from Lachish which had recently been defeated, along with the northern tribes of Israel and Syria. Their army seems unstoppable.
The mention of Lachish is important historically. Lachish was thirty miles south-west of Jerusalem. Archaeologists have discovered a pit there with the remains of about 1,500 casualties of Sennachaerib’s attack. In the British Museum, you can see the Assyrian carving depicting their siege of the city of Lachish, which was an important fortress city of Judah. - Enduring Word
On what do you rest this trust of yours - Hezekiah was defying this tyrant who wanted to bring the world under his rule. He has already been warned by the prophet Isaiah not to align with Egypt in Isaiah 19, 20 and 30.
Do you think that mere words - The ambassadors had already failed, and refusal of Sennacherib was not enough, he wasn't going to take no for an answer.
Behold, you are trusting in Egypt - The Assyrian is warning against this, but Hezekiah has already been warned by God. Assyria dominated Egypt and Cush, Judah's neighbors to the south. To a man of war, this seems the probable reason for Hezekiah's defiance.
“Egypt had made its one attempt to redeem its promises (28:14) and its army had been beaten at El Tekeh. The Rab-shakeh had himself seen this, but his words are more far-reaching and damaging, exposing the criminal stupidity of Judah’s leaders: surely, he said, they knew that anyone who ever trusted Egypt suffered for it.” (Motyer)
We trust in the Lord our God - This is where Isaiah has been directing all along, and sealed it in the scroll, with witnesses, that thus God has spoken. He will be the Deliverer of Jerusalem. Now the Rabshakeh will try to tear down such a claim of faith.
Whose high places and altars Hezekiah has removed - His argument is mute, Hezekiah did this in respect of God, Who did not authorize these high places, places of apostasy. In fact, he was one of only a few kings who reformed Jerusalem to that extent. It's like an unbeliever posing with a Bible, picking a verse out of context and acting like you should be moved to anything other than reproving them.
…2“Speak to Aaron, his sons, and all the Israelites and tell them this is what the LORD has commanded: 3‘Anyone from the house of Israel who slaughters an ox, a lamb, or a goat in the camp or outside of it4instead of bringing it to the entrance to the Tent of Meeting to present it as an offering to the LORD before His tabernacle—that man shall incur bloodguilt. He has shed blood and must be cut off from among his people.… Leviticus 17: 2-4
This command runs completely contrary to the way most people come to God in our culture. For the most part, Americans have an entirely individualistic way of coming to God, where each person makes up their own rules about dealing with God as they see Him. In the book Habits of the Heart, Robert Bellah and his colleagues interview a young nurse named Sheila Larson, whom they describe as representing many Americans’ experience and views on religion. Speaking about her own faith and how it operates in her life, she says: “I believe in God. I’m not a religious fanatic. I can’t remember the last time I went to church. My faith has carried me a long way. It is ‘Sheilaism.’ Just my own little voice.” This “pick-and-choose-as-I-go-along-according-to-my-inner-voice” approach is just like picking your own high place and altar to sacrifice to God the way you want to instead of the way God wants you to. - Enduring Word
The Lord said to me - Hezekiah already knows what the Lord has said through His prophet Isaiah. Yes, God allowed the Assyrians to carry out His justice upon Israel, Syria and Judah, but He also said it would go no further into Judah, into the city of Jerusalem. He told them not to go down to Egypt for help. Now, we were already warned that these things would take place, wars and rumors of such, so do we trust in the word of the living God, Who has told us before hand, or do we see the things he told us would happen, and now fear them more than the eternal Creator? If they carefully listened to God then they would see the error in the messenger now before them. He wants them to give up, to surrender an easy victory.
11-22. Do not speak to us in the language of Judah - They didn't want the people to hear, to become more afraid. They were told not to give the messenger an answer, and these men are obviously shaken to some great degree themselves.
Make your peace with me - He talks like the Devil, promising them their own vines until he takes them to a better place, but they just have to deny their king, and they can live.
That the Lord should deliver Jerusalem out of my hand - He has quite a record, a long list of defeats, including their own brothers to the north. None of their gods saved them. He doesn't understand, there is only one God, and Israel knew that God, but dishonored Him by disobedience, and He is eternal, so He is infinitely opposed to all He calls sin, and let that sink in to all our hearts, that we not take His name in vain. Will God deliver Jerusalem? He said He would, and God cannot lie.