What does Isaiah 16:8 mean?
ESV: For the fields of Heshbon languish, and the vine of Sibmah; the lords of the nations have struck down its branches, which reached to Jazer and strayed to the desert; its shoots spread abroad and passed over the sea.
NIV: The fields of Heshbon wither, the vines of Sibmah also. The rulers of the nations have trampled down the choicest vines, which once reached Jazer and spread toward the desert. Their shoots spread out and went as far as the sea.
NASB: For the fields of Heshbon have withered, the vines of Sibmah as well; The lords of the nations have trampled down its choice clusters Which reached as far as Jazer and wandered to the deserts; Its tendrils spread themselves out and passed over the sea.
CSB: For Heshbon’s terraced vineyards and the grapevines of Sibmah have withered. The rulers of the nations have trampled its choice vines that reached as far as Jazer and spread to the desert. Their shoots spread out and reached the sea.
NLT: The farms of Heshbon are abandoned; the vineyards at Sibmah are deserted. The rulers of the nations have broken down Moab — that beautiful grapevine. Its tendrils spread north as far as the town of Jazer and trailed eastward into the wilderness. Its shoots reached so far west that they crossed over the Dead Sea.
KJV: For the fields of Heshbon languish, and the vine of Sibmah: the lords of the heathen have broken down the principal plants thereof, they are come even unto Jazer, they wandered through the wilderness: her branches are stretched out, they are gone over the sea.
NKJV: For the fields of Heshbon languish, And the vine of Sibmah; The lords of the nations have broken down its choice plants, Which have reached to Jazer And wandered through the wilderness. Her branches are stretched out, They are gone over the sea.
Verse Commentary:
In this passage, Isaiah has commanded everyone to mourn the loss of the raisin cakes of Kir-hareseth (Isaiah 16:7). These cakes were apparently a well-loved delicacy that may have been exported to other nations. The production of the raisin cakes was lost when the invading armies destroyed the cities of Moab. Moab's economy and agricultural would have been decimated by the invasion, taking away the means that made the nation wealthy. This mourning, in a way, maintains a separation from the arrogant people of Moab, who are effectively told to grieve for themselves (Isaiah 16:6).

Isaiah goes into further detail regarding the destruction of the nation of Moab. He describes the deteriorating fields of Heshbon in the north. Nearby, the vine of Sibmah has also been struck down, perhaps by Assyria. Poetically, he says this grapevine thrived and reached Jazer, then farther north, and reaching all the way to eastern deserts. The vine's tendrils crossed over the Dead Sea into Israel. This symbolically depicts the successful distribution of the Moabite fields. Their crops spread prolifically around the region.

The grapes used to make the raisin cakes and other products are now gone. This ends both the enjoyment of the grapes and all the economic trading those products created to the north, east, and west. In other words, Moab's suffering had just begun with the attacks. Those who survived would not be able to return to the lives they once knew.
Verse Context:
Isaiah 16:1–14 begins with an official request to settle in Judah, spoken by Moabite refugees. This request is followed by a declaration that a descendant of David will establish the throne of Israel with love and righteousness when the oppressor is no more. Isaiah points to the arrogance of Moab regarding their abundance. This pride will be shown to be empty talk since it can be taken away in a night. Isaiah calls everyone to wail for Moab's losses and weep for the end of the grape harvest and its products. He reveals the judgment will fall in three years.
Chapter Summary:
The refugees of Moab send a tribute to Jerusalem and make an official request to shelter in Judah due to the oppression of the enemy in their own land. After the oppressor is no more, the throne of the Messiah will be established in Israel. Moab's pride and arrogance about their abundance are revealed to be empty talk since it can all be taken away in a night. Isaiah calls everyone to wail and mourn for the suffering of Moab. He weeps for the loss of the grape harvest. The prophet announces this judgement will happen in three years.
Chapter Context:
Prior chapters included predictions about Assyria, Babylon, and Philistia. Chapter 15 introduces a prophecy about an enemy invading Moab. Chapter 16 finds the Moabite refugees in Sela. They ask Judah for shelter. Isaiah points to the pride and arrogance of Moab about their wealth that can be taken away in a single night. He calls everyone to mourn with him for the loss of the grape harvest and its products in Moab. The Moabites' prayers to their god will not prevent judgment from falling on them in three years. The next prophecy, in chapter 17, deals with Damascus.
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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