What does Isaiah 36:16 mean?
ESV: 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,
NIV: "Do not listen to Hezekiah. This is what the king of Assyria says: Make peace with me and come out to me. Then each of you will eat fruit from your own vine and fig tree and drink water from your own cistern,
NASB: Do not listen to Hezekiah,’ for this is what the king of Assyria says: ‘ Surrender to me and come out to me, and eat, each one, of his vine and each of his fig tree, and each drink of the waters of his own cistern,
CSB: Don’t listen to Hezekiah, for this is what the king of Assyria says: "Make peace with me and surrender to me. Then every one of you may eat from his own vine and his own fig tree and drink water from his own cistern
NLT: Don’t listen to Hezekiah! These are the terms the king of Assyria is offering: Make peace with me — open the gates and come out. Then each of you can continue eating from your own grapevine and fig tree and drinking from your own well.
KJV: Hearken not to Hezekiah: for thus saith the king of Assyria, Make an agreement with me by a present, and come out to me: and eat ye every one of his vine, and every one of his fig tree, and drink ye every one the waters of his own cistern;
NKJV: Do not listen to Hezekiah; for thus says the king of Assyria: ‘Make peace with me by a present and come out to me; and every one of you eat from his own vine and every one from his own fig tree, and every one of you drink the waters of his own cistern;
Verse Commentary:
Through a skillful spokesman, a Rabshaqeh, King Sennacherib of Assyria is trying to coerce the people of Jerusalem to give up without a fight. Resistance will bring the horror of a siege (Isaiah 36:12). Assyria deliberately took on a reputation for cruel sadism against their enemies. Facing impossible odds (Isaiah 36:4–10), the people will be tempted to give up.

To add more pressure, the Assyrian commander offers incentive to anyone who surrenders now. They will be allowed to live in peace on their own land before they are relocated to comfort in Assyria (Isaiah 36:17). They can spend their remaining days in this country in comfort and peace. These ultimatums are delivered in the people's own language. This seems to include a common Hebrew expression often used to describe peace and security (1 Kings 4:25; 5:5; Micah 4:4).

However, the people have been given strict instructions to offer no response (Isaiah 36:21). Given Assyria's terrible reputation and recent broken word (2 Kings 18:17–18), the people would have plenty of reasons to doubt the offer.
Verse Context:
Isaiah 36:11–22 records psychological warfare from the commander of the Assyrian army. He shouts in the local dialect so everyone can experience terror. The speech promises horrors of siege and death unless the people surrender now. The Assyrian notes that no other nation's gods have stopped this invasion. Nor has any supernatural force protected the territories of Israel and Judah. Jerusalem seems to have no earthly hope, and Hezekiah's messengers wisely say nothing before returning to the city in grief.
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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