Isaiah Chapter 27
Isaiah 27, Ordering the Kingdom of the LORD
Isaiah 27 closes the section that began in Isaiah 24. These chapters move from worldwide judgment, to kingdom praise, to the strong city of God, and now to the ordered triumph of the Lord’s kingdom. In this chapter, the Lord defeats Leviathan, restores Israel as His fruitful vineyard, covers Jacob’s iniquity, destroys idolatry, makes the city of man desolate, and regathers the children of Israel one by one to worship Him in the holy mount at Jerusalem. The notes provided cover Isaiah 27:1-13, including the defeat of the serpent, Israel’s future blessing, mercy upon Jacob, judgment upon the world system, and the final regathering of Israel from Assyria and Egypt.
Isaiah 27:1
Isaiah 27:1, 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 dragon that is in the sea.”
Isaiah begins again with the phrase “In that day.” This connects Isaiah 27 with the larger prophetic section of Isaiah 24 through 27. The day in view is the day of the Lord’s triumph, the day when Messiah’s kingdom is established, the proud city of man is brought down, the righteous enter the strong city of God, death is swallowed up in victory, and the Lord reigns gloriously from Mount Zion and Jerusalem.
The Lord is pictured with “his sore and great and strong sword.” This is the weapon of divine judgment. The sword is severe, great, and strong because the enemy being judged is not ordinary. The Lord’s victory is complete because His power is absolute. No rebellious force, earthly or spiritual, can withstand the sword of the Lord.
The enemy is called “leviathan the piercing serpent,” and again “leviathan that crooked serpent.” Leviathan is described as serpent like, twisting, dangerous, hostile, and connected with the sea. The language is vivid and deliberately terrifying. The serpent imagery immediately brings the reader back to Genesis 3, where Satan appeared in serpent form and deceived Eve.
Genesis 3:1-5, KJV, “Now the serpent was more subtil than any beast of the field which the LORD God had made. And he said unto woman, Yea, hath God said, Ye shall not eat of every tree of garden? And woman said unto serpent, We may eat of fruit of trees of garden: But of fruit of tree which in midst of garden, God hath said, Ye shall not eat of it, neither shall ye touch it, lest ye die. And serpent said unto woman, Ye shall not surely die: For God doth know that in day ye eat thereof, then your eyes shall opened, and ye shall be as gods, knowing good and evil.”
The serpent in Eden introduced deception, rebellion, and death into human history. Isaiah 27 shows that the serpent’s final destiny is not victory, but destruction. The Lord will punish him and slay the dragon that is in the sea.
The sea often represents danger, chaos, nations, and hostile power. In Revelation, the beast rises from the sea, showing a connection between satanic power, Gentile world dominion, and the final Antichrist system.
Revelation 13:1-4, KJV, “And I stood upon sand of sea, and saw beast rise up out of sea, having seven heads and ten horns, and upon his horns ten crowns, and upon his heads name of blasphemy. And beast which I saw was like unto leopard, and his feet were as feet of bear, and his mouth as mouth of lion: and dragon gave him his power, and his seat, and great authority. And I saw one of his heads as it were wounded to death; and deadly wound was healed: and all world wondered after beast. And they worshipped dragon which gave power unto beast: and they worshipped beast, saying, Who like unto beast? who is able to make war with him?”
Revelation makes clear that the dragon empowers the beast. Isaiah’s dragon in the sea therefore fits the broader biblical pattern of satanic opposition manifesting through world power. While some interpreters reduce Leviathan to mythological imagery or symbolic national power, the biblical context allows for a much deeper reality. Satan can manifest through serpent imagery, dragon imagery, and beastly world systems. The final point is unmistakable, the Lord will slay him.
Other Old Testament passages also describe Leviathan as a mighty creature connected with the sea and subject to God’s power.
Psalm 74:13-14, KJV, “Thou didst divide sea by thy strength: thou brakest heads of dragons in waters. Thou brakest heads of leviathan in pieces, and gavest him to meat to people inhabiting wilderness.”
Psalm 104:25-26, KJV, “So is this great and wide sea, wherein are things creeping innumerable, both small and great beasts. There go ships: there is that leviathan, whom thou hast made to play therein.”
Job 41:1, KJV, “Canst thou draw out leviathan with hook? or his tongue with cord which thou lettest down?”
These passages reinforce the greatness and terror associated with Leviathan, while also showing that Leviathan remains under God’s authority. Man cannot master Leviathan, but God can. That is the point of Isaiah 27:1. The ultimate enemy of God and His people will be punished and slain by the Lord Himself.
This verse points to the final defeat of Satan.
Revelation 20:1-3, KJV, “And I saw angel come down from heaven, having key of bottomless pit and great chain in his hand. And he laid hold on dragon, that old serpent, which Devil, and Satan, and bound him thousand years, And cast him into bottomless pit, and shut him up, and set seal upon him, that he should deceive nations no more, till thousand years should fulfilled: and after that he must loosed little season.”
Revelation 20:10, KJV, “And devil that deceived them was cast into lake of fire and brimstone, where beast and false prophet are, and shall tormented day and night for ever and ever.”
Isaiah sees the day when the Lord’s kingdom victory includes the defeat of the serpent, the dragon, and the hostile power behind rebellious world systems. The kingdom of Messiah is not merely political reform. It is the overthrow of satanic rebellion.
Isaiah 27:2-6
Isaiah 27:2-6, KJV, “In that day sing ye unto her, vineyard of red wine. I the LORD do keep it; I will water it every moment: lest any hurt it, I will keep it night and day. Fury not in me: who would set briers and thorns against me in battle? I would go through them, I would burn them together. Or let him take hold of my strength, that he may make peace with me; and he shall make peace with me. He shall cause them that come of Jacob to take root: Israel shall blossom and bud, and fill face of world with fruit.”
The imagery changes from the defeat of Leviathan to the restoration of Israel as the Lord’s vineyard. Isaiah says, “In that day sing ye unto her, A vineyard of red wine.” This is a joyful song over the vineyard. Earlier in Isaiah, the vineyard imagery was used to expose Israel’s failure.
Isaiah 5:1-7, KJV, “Now will I sing to my wellbeloved song of my beloved touching his vineyard. My wellbeloved hath vineyard in very fruitful hill: And he fenced it, and gathered out stones thereof, and planted it with choicest vine, and built tower in midst of it, and also made winepress therein: and he looked that it should bring forth grapes, and it brought forth wild grapes. And now, O inhabitants of Jerusalem, and men of Judah, judge, I pray you, betwixt me and my vineyard. What could have been done more to my vineyard, that have not done in it? wherefore, when I looked that it should bring forth grapes, brought it forth wild grapes? And now go to; I will tell you what I will do to my vineyard: I will take away hedge thereof, and it shall eaten up; and break down wall thereof, and it shall trodden down: And I will lay it waste: it shall not pruned, nor digged; but there shall come up briers and thorns: I will also command clouds that they rain no rain upon it. For vineyard of LORD of hosts is house of Israel, and men of Judah his pleasant plant: and he looked for judgment, but behold oppression; for righteousness, but behold cry.”
In Isaiah 5, Israel was the unfruitful vineyard that brought forth wild grapes. God had given every privilege, but Israel produced corruption. In Isaiah 27, the vineyard is restored. The Lord Himself keeps it, waters it, protects it, and causes it to bear fruit. The contrast is intentional. Israel’s failure is not the end of Israel’s story. God’s covenant faithfulness brings future restoration.
The Lord says, “I the LORD do keep it; I will water it every moment.” The restoration of Israel is not secured by Israel’s strength, but by the Lord’s care. He waters it constantly. He guards it constantly. He says, “lest any hurt it, I will keep it night and day.” This is continuous divine protection. The vineyard that was once exposed to judgment is now guarded by the Lord Himself.
The phrase “Fury is not in me” shows a change in God’s posture toward restored Israel. His wrath against their covenant rebellion has been dealt with. His discipline has accomplished its purpose. In the kingdom, Israel is not under divine fury, but under divine favor.
The Lord then asks, “who would set briers and thorns against me in battle?” Briers and thorns represent worthless opposition, hostile growth, and enemies of the vineyard. If they rise against the Lord, He says, “I would go through them, I would burn them together.” No enemy can successfully attack the vineyard God keeps.
Yet verse 5 gives an offer of peace, “Or let him take hold of my strength, that he may make peace with me; and he shall make peace with me.” This is a remarkable statement. Before judgment falls, the Lord offers peace. The enemies pictured as briers and thorns may either be burned or take hold of God’s strength and make peace with Him.
This is grace. The God who can destroy rebels also invites them to be reconciled. Peace with God does not come by negotiating terms, defending oneself, or offering human merit. It comes by taking hold of His strength. Man has no strength adequate to save himself. He must lay hold of the strength God provides.
Romans 5:1, KJV, “Therefore being justified by faith, we have peace with God through our Lord Jesus Christ.”
Peace with God comes through Christ. Isaiah’s invitation finds its fullest answer in the gospel. The sinner does not make peace by self improvement. He receives peace through faith in the Lord’s provision.
Verse 6 gives the result, “He shall cause them that come of Jacob to take root: Israel shall blossom and bud, and fill face of world with fruit.” This is national restoration and kingdom fruitfulness. Israel will take root, blossom, bud, and fill the world with fruit. The nation that was judged for wild grapes will one day become fruitful under Messiah’s reign.
This points to the future restoration of Israel in the kingdom. It does not erase the church, and it does not replace Israel with the church. Israel is named. Jacob is named. The promise concerns the future fruitfulness of the covenant people under the Lord’s care.
Romans 11:25-27, KJV, “For I would not, brethren, that ye should ignorant of this mystery, lest ye should wise in your own conceits; that blindness in part happened to Israel, until fulness of Gentiles be come in. And so all Israel shall saved: as it written, There shall come out of Sion Deliverer, and shall turn away ungodliness from Jacob: For this my covenant unto them, when I shall take away their sins.”
Israel’s present blindness is partial and temporary. The Deliverer will come out of Zion and turn away ungodliness from Jacob. Isaiah 27:6 shows the fruitfulness that follows that restoration.
There is also a personal application for believers now. Fruitfulness comes through abiding in the Lord’s care and strength.
John 15:1-5, KJV, “I am true vine, and my Father husbandman. Every branch in me that beareth not fruit he taketh away: and every branch that beareth fruit, he purgeth it, that it may bring forth more fruit. Now ye clean through word which I have spoken unto you. Abide in me, and I in you. As branch cannot bear fruit of itself, except it abide in vine; no more can ye, except ye abide in me. I am vine, ye branches: He that abideth in me, and I in him, same bringeth forth much fruit: for without me ye can do nothing.”
Israel’s future fruitfulness and the believer’s present fruitfulness both depend upon the Lord’s life, care, and strength.
Isaiah 27:7-9
Isaiah 27:7-9, KJV, “Hath he smitten him, as he smote those that smote him? or is he slain according to slaughter of them that are slain by him? In measure, when it shooteth forth, thou wilt debate with it: he stayeth his rough wind in day of east wind. By this therefore shall iniquity of Jacob be purged; and this all fruit to take away his sin; when he maketh all stones of altar as chalkstones that beaten in sunder, groves and images shall not stand up.”
Isaiah now explains the mercy of God in His dealings with Israel. The Lord asks, “Hath he smitten him, as he smote those that smote him?” In other words, has God struck Israel the same way He struck Israel’s enemies? The answer is no. God disciplined Israel severely, but He did not destroy Israel as He destroyed the nations that sought Israel’s ruin.
This is the mercy of covenant discipline. God’s chastening of His people is real, but it is measured. Verse 8 says, “In measure.” The Lord contends with Israel, but not without limit. He sends the rough wind, but He also restrains it. The east wind could be destructive, hot, and severe, yet even in judgment God governs the intensity.
Jeremiah 30:11, KJV, “For I with thee, saith LORD, to save thee: though I make full end of all nations whither I have scattered thee, yet will I not make full end of thee: but I will correct thee in measure, and will not leave thee altogether unpunished.”
This verse states the same principle. God may make a full end of nations, but He will not make a full end of Israel. He corrects Israel in measure. He does not leave sin unpunished, but He does not abandon His covenant promises.
Verse 9 says, “By this therefore shall the iniquity of Jacob be purged.” The Lord’s discipline has a purifying purpose. God is not merely punishing Israel, He is removing sin. The ultimate purging of Jacob’s iniquity comes through the New Covenant and the finished work of Messiah. Israel’s national restoration requires the removal of sin, not merely political return to the land.
Zechariah 13:1, KJV, “In that day there shall fountain opened to house of David and to inhabitants of Jerusalem for sin and for uncleanness.”
God will open a fountain for cleansing. Isaiah 27:9 points to that future purging.
The visible fruit of sin being taken away is the destruction of idolatry, “when he maketh all the stones of the altar as chalkstones that are beaten in sunder, groves and images shall not stand up.” False altars, groves, and images will be smashed. Israel’s idolatry will not continue into the kingdom. God’s mercy does not preserve idols. It destroys them.
This is important. Forgiveness does not mean God becomes tolerant of idols. When God covers sin, He also removes the rival worship that produced it. True restoration includes the destruction of false worship.
Ezekiel 36:25-27, KJV, “Then will I sprinkle clean water upon you, and ye shall clean: from all your filthiness, and from all your idols, will I cleanse you. New heart also will I give you, and new spirit will I put within you: and I will take away stony heart out of your flesh, and I will give heart of flesh. And I will put my spirit within you, and cause you to walk in my statutes, and ye shall keep judgments, and do them.”
The Lord cleanses Israel from idols, gives a new heart, and causes obedience. Isaiah 27:7-9 fits that same future restoration.
Isaiah 27:10-11
Isaiah 27:10-11, KJV, “Yet defenced city shall desolate, and habitation forsaken, and left like wilderness: there shall calf feed, and there shall he lie down, and consume branches thereof. When boughs thereof are withered, they shall broken off: women come, and set them on fire: for it people of no understanding: therefore he that made them will not have mercy on them, and he that formed them will shew them no favour.”
The focus now returns to the fortified city, the city of man. While Israel is restored as the Lord’s vineyard, the proud city of the world system is made desolate. The “defenced city” represents human strength organized apart from God. It is fortified, but it cannot stand. It becomes desolate, forsaken, and like a wilderness.
This is the same contrast seen earlier in Isaiah 26. The strong city of God is defended by salvation, but the lofty city of man is brought down to the dust. Here, the fortified city is abandoned. Animals feed there. Calves lie down. Branches are consumed. What once looked strong becomes pasture and wasteland.
The withered boughs are broken off and used for fire. This is total humiliation. The city’s former glory becomes fuel. The world system, with all its pride, technology, wealth, culture, and military confidence, will be reduced to uselessness under the judgment of God.
The reason is given, “for it is a people of no understanding.” This does not mean they lacked intelligence. The world often has technical intelligence, political intelligence, commercial intelligence, and military intelligence. But it lacks spiritual understanding. It does not know God. It does not fear Him. It does not submit to His truth.
Romans 1:21-22, KJV, “Because that, when they knew God, they glorified not as God, neither were thankful; but became vain in imaginations, and their foolish heart darkened. Professing themselves wise, they became fools.”
The world can profess wisdom while being spiritually foolish. That is the condition of the city of man.
The judgment is severe, “therefore he that made them will not have mercy on them, and he that formed them will shew them no favour.” The Creator has rights over His creatures. If those He made persist in rebellion, He is righteous to judge them. Mercy rejected eventually gives way to judgment.
This is terrifying language. The world system often assumes that God’s mercy is automatic, sentimental, and endless regardless of repentance. Isaiah says otherwise. There comes a point where the One who made them shows no favor. That is not because God is unjust, but because persistent rebellion has refused mercy.
Proverbs 29:1, KJV, “He, that being often reproved hardeneth his neck, shall suddenly destroyed, and that without remedy.”
The fortified city warns every generation not to place hope in the world system. It will be desolate. It will be forsaken. It will not receive favor when the Lord’s judgment falls.
Isaiah 27:12-13
Isaiah 27:12-13, KJV, “And it shall come to pass in that day, that LORD shall beat off from channel of river unto stream of Egypt, and ye shall gathered one by one, O ye children of Israel. And it shall come to pass in that day, that great trumpet shall blown, and they shall come which were ready to perish in land of Assyria, and outcasts in land of Egypt, and shall worship LORD in holy mount at Jerusalem.”
The chapter ends with regathering and worship. Again Isaiah says, “in that day.” The same day that brings judgment upon the serpent, restoration to Israel, destruction of idols, and desolation to the city of man also brings the regathering of Israel.
The Lord will “beat off from the channel of the river unto the stream of Egypt.” This describes a gathering from the broad range of Israel’s promised territory and dispersion. The Lord is pictured as carefully threshing or beating out His grain, separating and gathering His people. The phrase “ye shall be gathered one by one, O ye children of Israel” is deeply personal. God does not merely gather Israel as a mass. He gathers them one by one. Each person is known. Each scattered child is seen.
This is covenant faithfulness. Israel’s scattering was real, but it is not final. God promised regathering.
Deuteronomy 30:3-5, KJV, “That then LORD thy God will turn thy captivity, and have compassion upon thee, and will return and gather thee from all nations, whither LORD thy God hath scattered thee. If any of thine be driven out unto outmost parts of heaven, from thence will LORD thy God gather thee, and from thence will fetch thee: And LORD thy God will bring thee into land which thy fathers possessed, and thou shalt possess it; and he will do thee good, and multiply thee above thy fathers.”
The Lord promised to gather Israel from the nations and bring them back to the land. Isaiah 27:12-13 is part of that same prophetic hope.
Verse 13 says, “the great trumpet shall be blown.” The trumpet signals gathering, announcement, and divine summons. Those ready to perish in Assyria and the outcasts in Egypt will come. Assyria and Egypt represent the lands of oppression, exile, and dispersion. The Lord calls His people home from the places where they were scattered.
This connects with the Lord’s teaching in the Olivet Discourse.
Matthew 24:29-31, KJV, “Immediately after tribulation of those days shall sun darkened, and moon shall not give light, and stars shall fall from heaven, and powers of heavens shall shaken: And then shall appear sign of Son of man in heaven: and then shall all tribes of earth mourn, and they shall see Son of man coming in clouds of heaven with power and great glory. And he shall send angels with great sound of trumpet, and they shall gather together his elect from four winds, from one end of heaven to other.”
This gathering occurs after the Tribulation and is connected with the visible coming of the Son of Man. It is distinct from the catching up of the church described in 1 Thessalonians 4. Isaiah 27 points to Israel’s regathering for kingdom worship.
The purpose of the gathering is worship, “and shall worship the LORD in the holy mount at Jerusalem.” This is the final note of the chapter. The regathered children of Israel come not merely to possess land, but to worship the Lord. The holy mount at Jerusalem is the center of kingdom worship. This fits the premillennial expectation that Messiah will reign from Jerusalem and the nations will worship the Lord there.
Zechariah 14:16, KJV, “And it shall come to pass, that every one that left of all nations which came against Jerusalem shall even go up from year to year to worship King, LORD of hosts, and to keep feast of tabernacles.”
Isaiah 27 ends with ordered kingdom restoration. The serpent is slain. Israel is fruitful. Jacob’s iniquity is purged. Idols are destroyed. The city of man is desolate. Israel is gathered one by one. The great trumpet sounds. The outcasts return. The Lord is worshiped in the holy mount at Jerusalem.
