What does Isaiah 37:27 mean?
ESV: while their inhabitants, shorn of strength, are dismayed and confounded, and have become like plants of the field and like tender grass, like grass on the housetops, blighted before it is grown.
NIV: Their people, drained of power, are dismayed and put to shame. They are like plants in the field, like tender green shoots, like grass sprouting on the roof, scorched before it grows up.
NASB: Therefore their inhabitants were powerless, They were shattered and put to shame; They were like the vegetation of the field and the green grass, Like grass on the housetops that is scorched before it has grown.
CSB: Their inhabitants have become powerless, dismayed, and ashamed. They are plants of the field, tender grass, grass on the rooftops, blasted by the east wind.
NLT: That is why their people have so little power and are so frightened and confused. They are as weak as grass, as easily trampled as tender green shoots. They are like grass sprouting on a housetop, scorched before it can grow lush and tall.
KJV: Therefore their inhabitants were of small power, they were dismayed and confounded: they were as the grass of the field, and as the green herb, as the grass on the housetops, and as corn blasted before it be grown up.
NKJV: Therefore their inhabitants had little power; They were dismayed and confounded; They were as the grass of the field And the green herb, As the grass on the housetops And grain blighted before it is grown.
Verse Commentary:
While Assyria's king Sennacherib flatters himself (Isaiah 37:24–25), the Lord claims responsibility for all the terror and destruction the Assyrians have brought (Isaiah 37:26). It was part of His plan to judge Israel (Isaiah 8:6–8) as well as other people groups. Sennacherib has foolishly assumed glory for that success for himself and his ancestors before him. They had defeated not just all the kings of all the nations, but they had defeated the gods those peoples served, as well, apparently burning their idols to ash (Isaiah 37:18–19).

It's true that those defeated by Assyria were utterly dominated. God compares the conquered people to diseased or sunburnt plants easily cut down before they can grow. But Sennacherib is wrong to assume that his conquests are the result of his own greatness. Rather, this is a plan God has been using to judge the nations of earth (Isaiah 10:5–11). The end of that plan, however, brings the same judgment back onto these aggressive cultures (Isaiah 10:12–19).

God knows everything Sennacherib has said or done (Hebrews 4:13) and will judge the arrogant king by thoroughly defeating him (Isaiah 37:28–29).
Verse Context:
Isaiah 37:21–38 contains the Lord's response to Hezekiah's humble prayer (Isaiah 37:14–20). Through Isaiah, the Lord first addresses Sennacherib in a poem. He tells the most powerful man on earth at the time that God will turn him around and send him home. Next the Lord promises Hezekiah that Sennacherib will never even approach Jerusalem, let alone attack it. The remnant of Judah will survive and thrive. As the Assyrians plan to engage in a different battle, the Lord destroys nearly the entire army in a single night. Sennacherib goes home. He is later killed by his sons.
Chapter Summary:
Hezekiah is overcome with grief at news that Sennacherib has mocked the Lord and is coming to destroy Jerusalem. God reassures Hezekiah that the Asyrian king will return home to be killed there. Hezekiah prays in the temple, asking the Lord to defend His name and save Judah. Through Isaiah, the Lord reveals to Hezekiah that Jerusalem will not be touched. Assyria's army won't even have the chance to attack. Responding to their aggression and blasphemy, the "angel of the Lord" virtually wipes out the gigantic Assyrian army overnight. Sennacherib returns home and is later killed by his sons.
Chapter Context:
Isaiah 37 continues the narrative started in Isaiah 36. Assyrian messengers threaten to bring their enormous, nearby army to take Jerusalem. Hezekiah seeks God in response and is reassured that Jerusalem will not see so much as a single Assyrian arrow. The Lord promises to save the city and make the survivors prosper. The angel of the Lord kills an overwhelming number of Assyrian soldiers overnight. Sennacherib returns home and is eventually killed by his own sons. Hezekiah will then face a serious illness and be granted a brief reprieve by God (Isaiah 38).
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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