What does Isaiah 36:5 mean?
ESV: Do you think that mere words are strategy and power for war? In whom do you now trust, that you have rebelled against me?
NIV: You say you have counsel and might for war—but you speak only empty words. On whom are you depending, that you rebel against me?
NASB: I say, ‘Your plan and strength for the war are only empty words.’ Now on whom have you relied, that you have revolted against me?
CSB: You think mere words are strategy and strength for war. Who are you now relying on that you have rebelled against me?
NLT: Do you think that mere words can substitute for military skill and strength? Who are you counting on, that you have rebelled against me?
KJV: I say, sayest thou, (but they are but vain words) I have counsel and strength for war: now on whom dost thou trust, that thou rebellest against me?
NKJV: I say you speak of having plans and power for war; but they are mere words. Now in whom do you trust, that you rebel against me?
Verse Commentary:
The Rabshakeh of Sennacherib (Isaiah 36:4) is the king's spokesperson and perhaps most trusted advisor. He confronts representatives of King Hezekiah outside Jerusalem. He has not been polite, launching immediately into a challenging question: What are you trusting to save yourself?

Hezekiah, along with other nations in the region, made the bold decision not to pay tribute to the Assyrians after the recent death of Sennacherib's father, Sargon II. Many were hopeful that the Assyrians had been weakened after Sargon II had been killed, so they took the opportunity to band together in defiance. Sennacherib's reign of terror through the land had proven that unwise, so far.

Isaiah doesn't mention it here, but Hezekiah tried to pay off Sennacherib before this meeting (2 Kings 18:13–16). He sent a message saying he had done wrong and offering to pay any amount if Sennacherib would just go away. Sennacherib named his price and Hezekiah scavenged silver and gold from the treasury and temple. Then Sennacherib sent his men to let Hezekiah know they were taking the city anyway.

Now Sennacherib's messenger asks Hezekiah if words could possibly win a war. Hezekiah rebelled against Assyria. Who did he imagine he could trust to save him from Sennacherib's massive army? Sennacherib's messenger is clearly mocking Hezekiah. He has already defeated every earthly power Judah may have looked to for rescue. This message is like a cat playing with a mouse before the death blow.
Verse Context:
Isaiah 36:4–10 is the Assyrian king's message to Jerusalem, delivered by a royal commander or "Rabshakeh." The spokesman mocks Israel for trying to ally with Egypt, who is now defeated. He sneers at the idea of Israel's God having power. He even dares to give Israel 2,000 war horses if they have men to ride them, which they do not. The Assyrian even claims that it was Israel's God who sent him there in the first place.
Chapter Summary:
Sennacherib and the Assyrian army conquer all of Judah except for Jerusalem. There, a remnant of the people waits inside the walls. Sennacherib sends a messenger to meet with Hezekiah's officials. The messenger taunts Hezekiah, mocking their attempts at alliances as well as their faith in God. This commander, also called "the Rabshakeh" calls out in the local Hebrew language so everyone will understand. He offers life and prosperity to those who surrender now. In his opinion, none of the gods of any of the nations the Assyrians have defeated were able to stop them. So why will the Lord God of Israel be any different?
Chapter Context:
Isaiah 36 shifts from poetic prophecies to the historical account of an Assyrian army's threats against Judah. Sennacherib's army conquers everything in Judah other except for Jerusalem. An Assyrian messenger taunts the people and tells them that no gods have stopped Assyria yet, so they shouldn't trust in Judah's God, either. Diplomats return to King Hezekiah in Jerusalem with this news. Hezekiah will seek help from Isaiah, pray to God, and receive a spectacular miraculous rescue (Isaiah 37).
Book Summary:
Isaiah is among the most important prophetic books in the entire Bible. The first segment details God's impending judgment against ancient peoples for sin and idolatry (Isaiah 1—35). The second part of Isaiah briefly explains a failed assault on Jerusalem during the rule of Hezekiah (Isaiah 36—39). The final chapters predict Israel's rescue from Babylonian captivity (Isaiah 40—48), the promised Messiah (Isaiah 49—57), and the final glory of Jerusalem and God's people (Isaiah 58—66).
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