What does Isaiah 27:1 mean?
ESV: In that day the Lord with his hard and great and strong sword will punish Leviathan the fleeing serpent, Leviathan the twisting serpent, and he will slay the dragon that is in the sea.
NIV: In that day, the Lord will punish with his sword— his fierce, great and powerful sword— Leviathan the gliding serpent, Leviathan the coiling serpent; he will slay the monster of the sea.
NASB: On that day the Lord will punish Leviathan the fleeing serpent, With His fierce and great and mighty sword, Even Leviathan the twisted serpent; And He will kill the dragon who lives in the sea.
CSB: On that day the Lord with his relentless, large, strong sword will bring judgment on Leviathan, the fleeing serpent—Leviathan, the twisting serpent. He will slay the monster that is in the sea.
NLT: In that day the Lord will take his terrible, swift sword and punish Leviathan, the swiftly moving serpent, the coiling, writhing serpent. He will kill the dragon of the sea.
KJV: In that day the Lord with his sore and great and strong sword shall punish leviathan the piercing serpent, even leviathan that crooked serpent; and he shall slay the dragon that is in the sea.
NKJV: In that day the Lord with His severe sword, great and strong, Will punish Leviathan the fleeing serpent, Leviathan that twisted serpent; And He will slay the reptile that is in the sea.
Verse Commentary:
Commentators are divided about whether this verse stands alone or completes the end of the prior chapter (Isaiah 26:20–21). It is clearly about the Lord's final victory when His judgment of the earth will be followed by His kingdom on earth.

Using symbolism, Isaiah says the Lord will defeat a terrible creature. The name Leviathan is mentioned five times in the Old Testament. One of these credits the Lord with crushing Leviathan's multiple heads (Psalm 74:14). Job chapter 41 depicts a creature which is untamable and monstrous, though this seems to be a different beast than the one Isaiah mentions. Job is meant to understand that God alone created the beast and He alone could control it. Isaiah refers to something related to the end times.

The mystery of this name has fired the imaginations of readers for thousands of years. Ancient Ugaritic and Canaanite mythologies describe a twisting, multi-headed sea serpent. This monster typically symbolizes chaos. Isaiah's words would be a concise way of explaining how God will finally conquer all chaos and evil during the end times.

An alternative interpretation is that this "Leviathan" represents the large nations who opposed Israel and Judah, such as Egypt, Assyria, and Babylon, whose religions included this monster.
Verse Context:
Isaiah 27:1 speaks of a point in Isaiah's future when God will restore Israel from all her suffering. This uses imagery of "Leviathan;" in this context, this refers to a gigantic mythical sea monster representing chaos. Isaiah uses this convenient metaphor without suggesting that such a creature literally exists.
Chapter Summary:
This passage often uses the phrase "in that day" referring to the end times when the Lord reigns on earth as king. Then, the Israelites will be fully restored. Their "fruit" will fill the world. The nations God used as tools to judge His people will themselves be judged, but much more harshly. Defeats will happen in the meantime, but the Lord will only measure out enough discipline to trigger Israel's repentance. There will be no compassion for those who refuse to repent. He will bring all His people home to worship Him in Jerusalem in the end.
Chapter Context:
Isaiah 27 completes a section (Isaiah 24—27) about the time when the Lord will make all things right. That description begins with the Lord's judgment of the earth (Isaiah 24:1) and ends with the redemption and restoration of Israel (Isaiah 27:6). The nations God used to judge Israel will themselves be judged. The next section of Isaiah focuses on God's scathing words for those who opposed Him, including the failed leaders of Israel and Judah.
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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