Isaiah in this chapter describes God as the covenant keeping Husband of Israel. He lovingly cultivates His vineyard Israel for righteousness, but they bore rebellion instead of grapes. He called them to repent through judgment, ultimately sending His Son, Yeshua the Messiah, as both Judge and Redeemer. God’s purpose is to call God’s covenant people to examine their fruit and return to God. This was a call to them that also points to the days to come by receiving Messiah Yeshua, the true Vine.
The “vineyard” is explicitly identified as the house of Israel and Judah (v. 7). Ps 8:7-8 “You removed a vine from Egypt; You drove out the nations and planted it. You cleared the ground before it, And it took deep root and filled the land.
V 1 Describes God’s covenant love betrayed. God describes Israel as His beloved. Hosea echoes this love in 2:19-20: “I will betroth you to Me forever; Yes, I will betroth you to Me in righteousness and in justice, in lovingkindness and in compassion, And I will betroth you to Me in faithfulness. Then you will know the LORD.
This reflects God’s covenant relationship with Israel as described in Exodus 19:5–6 Now then, if you will indeed obey My voice and keep My covenant, then you shall be My own possession among all the peoples, for all the earth is Mine; and you shall be to Me a kingdom of priests and a holy nation.’
Deuteronomy 7:6–8 For you are a holy people to the LORD your God; the LORD your God has chosen you to be a people for His own possession out of all the peoples who are on the face of the earth. “The LORD did not set His love on you nor choose you because you were more in number than any of the peoples, for you were the fewest of all peoples, but because the LORD loved you and kept the oath which He swore to your forefathers, the LORD brought you out by a mighty hand and redeemed you from the house of slavery, from the hand of Pharaoh king of Egypt.
V 2 We see God’s provision and expectations for His covenant people. God provided fertile land, choice vines, a watchtower, and a winepress. Using Hebrew word plays in v 7 “He looked for justice, but behold, bloodshed; For righteousness, but behold, a cry of distress. Isaiah says God looked for mishpat (justice) but saw mispach (bloodshed); for tzedakah (righteousness) but heard tzekah (cries of distress).
God’s care for Israel through the Torah, prophets, and the Temple was abundant. Yet what fruit did He find? Worthless fruit, He asks the same question of us today.
V 3-7 Describes God’s judgment for unfaithfulness. God removes His hedge of protection. The vineyard will be destroyed, a foreshadowing of the Babylonian exile in 586 BC and, later, the destruction of the Second Temple in 70 AD.
In Matthew 21:33–46, Yeshua directly references Isaiah 5. This parable of the vineyard climaxes in Israel’s leaders’ rejection of God’s Son, the Messiah. Ezekiel 34 complements this where God rebukes the false shepherds of Israel and promises to regather His scattered flock. In that chapter Ezekiel reveals God’s heart for His people. He will judge the false shepherds and personally seek His scattered sheep through His Messiah the ultimate Shepherd-King.
V 8-10 Begins six woes through v 23. The word “woe” in Scripture especially in the prophets is a term of divine warning, generally used to express grief, condemnation, or impending judgment. A common Yiddish expression that comes from this Hebrew word “hoy” is just “oy”. Here it serves as a call or alarm for impending judgment. “Woe” is more than just emotional grief but also a covenantal warning. That God sees the injustice or unrighteousness among His people. His patience has limits, and Judgment is coming unless there is repentance.
Each “woe” corresponds to a covenant violation. God is holding His people to the terms of covenant outlined in Exodus through Deuteronomy. The first woe is to the greed of God’s children. God rebukes those who accumulate land and wealth at the expense of others, violating His covenant design for justice, community, and stewardship. “Join house to house… field to field” The wealthy seized land from small farmers, creating economic monopolies.
This violates Leviticus 25 and the year of jubilee, where land was to be returned to the tribal portions given by Moses and Joshua. Greed violates God’s covenantz. Israel forgot that the land belonged to The Lord Psalm 24:1: The earth is the LORD’S, and all it contains, the world, and those who dwell in it.God gave the Land to Israel but there were conditions for them to remain in it. Deut 28 and Lev. 26 outline the blessings and curses that will come based on their obedience or disobedience to Covenant responsibilities associated with the Mosaic Covenant.
“Until you are left alone in the midst of the land” Ironically in their quest for more, they end up isolated, both physically and spiritually. Greed isolates but generosity builds community. God’s judgment was that these houses and properties were going to be left vacant.
V 11-12 The second woe is an indictment against those who overindulge in drinking. This reveals a progressive decay of society as people would “Rise up early… stay late”. From dawn to dusk, these individuals are consumed with pleasure-seeking, particularly drunkenness. Wine is not condemned, but its abuse and centrality to life is. This is not just about alcohol but a worldview that lives to escape rather than to seek God’s purpose in their lives. When entertainment, pleasure, or substances become our refuge we are sidetracked from the things that bring life to ourselves and others. Israel was meant to be a kingdom of priests (Exodus 19:6), but they behaved like pagan nations that God removed from His holy Land. The result of that lifestyle is spiritual blindness that loses sight of what God is doing and fail to see the work of His hands.
V 13-14 The Consequence of overindulgence will be exile and humiliation. “Therefore, My people are exiled for lack of knowledge…” “Lack of knowledge” refers to covenant knowledge, not information, but their relationship and reverence of God and submission and obedience to His Word. The leaders feast, but the people go hungry. This foreshadows the Babylonian exile, God’s judgment for covenant unfaithfulness. Sheol (the grave) is personified, “opening its mouth wide” to swallow those who rebel against The Lord.
V 15-17 Pride always leads to humiliation Proverbs 16:18: Pride goes before destruction, And a haughty spirit before stumbling. Human strength fails under God’s judgment. They are foolishly self-sufficient and unwilling to humbly receive the instruction and correction so necessary for wisdom’s blessings. This is why humility is so valuable. In contrast to fallen man, The Lord of hosts is exalted in justice and righteousness. This prepares the way for Isaiah 6, where Isaiah sees the Holy One exalted. In v 17 restoration is foreshadowed. After judgment, a remnant remains as the humble and dispossessed will inherit the land.
V 18-19 The third woe is to the scoffers who mock the coming of the Holy One of Israel. God is deeply grieved and angered by this. “Drag wrongdoing with cords of deceit”: This pictures people pulling sin behind them deliberately, not accidentally. They are attached to their sin and it includes self-deception, rationalizing sin, or distorting the truth to justify their evil. The imagery escalates as thin cords becomes “thick cart ropes”, suggesting bondage and stubborn persistence in carrying their sin. They are fully committed to their sinful ways. They have become comfortable in their rebellion while deceiving themselves. Sin, once small, becomes heavy and enslaving. They mock God by saying ‘Let Him hurry, let Him do His work quickly, so that we may see it. They ridicule Isaiah’s warnings and say, in effect: “If God’s judgment is real, let Him get on with it.” “The Holy One of Israel” is Isaiah’s signature title for God, pointing to His being set apart, faithful in covenant relationship, and moral perfection. We see this attitude described by Peter in 2 Peter 3:3–4: “In the last days mockers will come… saying, ‘Where is the promise of His coming?’”
V 20 The fourth woe was the perversion of good and evil light for darkness, bitter for sweet. This describes the fall of morals among those who reject God. Without the divine standards of God’s law, a good thing can be reinterpreted as something evil and something evil as good. Two examples are when expressing natural order in believing that men are women are women or euthanasia. Human reasoning and rationalizing can justify almost any act particularly if it is based on “Will it benefit me?” Much of the crime and immorality flows from our cultural redefinitions of right and wrong. People in any generation can and do reject the idea that they are doing wrong because they have no moral anchor. But human defiance and ignorance does not eliminate God’s truth revealed in His commands found in both Old and New Covenants.
V 21 The fifth woe is to the self-righteous who trust in man’s wisdom over the wisdom of God’s Word and the leading and abiding of God’s Holy Spirit. Paul writes of this in Romans 1:22, professing to be wise, they became fools.
V 22-23 The sixth woe returns to the theme of drunkenness and social injustice, echoing the concerns of the second woe in vv. 11–12. Using irony Isaiah mocks these men as “heroes” and “valiant or mighty men” terms used to describe veterans of war for their valor in battle. These people’s strength is not in battle, but in their capacity to mix and consume strong drink. Their fame is built on excess, not courage. Drunkenness deadens moral clarity and enables the abuse of authority, where justice is undermined. In v 8 the oppression of the poor was expressed in the amassing of houses and fields at others’ expense. This was coupled with corruption in the justice system. Judges and witnesses were being bribed to acquit the guilty, while the innocent were denied justice. This reflected on Israel’s God who is just, righteous and filled with mercy and compassion for the poor and needy. All of these woes reveal a nation that has lost its fear of the LORD and is ripe for divine judgment.
V 24-25 There are two therefore’s in these verses which answers why severe judgment was coming. God’s response is based on what has been revealed in the Torah. When “they reject and “despise what” God commands as the conditions for covenantal blessings then the covenantal curses come. Although the people may have looked at their deeds as merely a slight difference of interpretation, God saw them as a direct affront to his will, character, and authority. Their willful acts show no respect for God’s instructions. This kind of response from not just Israel but all mankind will eventually bring the fire of God’s judgment.
The second “therefore” in v 25 reemphasizes God’s wrath to motivate the listeners to accept the inevitability of God’s destruction, if there is no change. Repeatedly, both at the beginning and end of this verse, Isaiah reminds his listeners of His burning anger and his hand of judgment. The mention of God’s anger twice, the initial reference appears to be pointing to God’s past act of anger in the great earthquake that happened during the time of Amos around 765-760 BC (Amos 1:1; 2:13; 6:11; 8:8; 9:1). The second reference to God’s burning anger emphasizes that in spite of all God did in the past to punish them, his hand will continue to execute justice against sin in the future. God’s character has not changed since the days of Amos and Isaiah, and his hatred of sins has not diminished. Every person who despises what God reveals in Scripture should stop and pay attention to God’s just ways of dealing with sin.
God summons the nations as instruments of judgment. Historically fulfilled in Assyria, Babylon, Rome, but also prophetically looks ahead to the Day of the Lord. Yeshua warned of Jerusalem’s destruction in Luke 21:20–24, fulfilled in 70 CE. and the future judgment described in the days leading to Yeshua’s return to Jerusalem in Matthew 24-25.
The Song of the Vineyard reminds us that God planted Israel as a vineyard to bear fruit for His glory. When the fruit failed, He warned through the prophets that judgment would be coming. Ultimately, He sent His Son, the “true Vine” (John 15:1), came to restore His vineyard. In His first coming to bring the New Covenant for Jew and Gentile and in His second coming to restore Israel in her God given land. Yeshua is the true and faithful Israelite, bearing the fruit Israel was meant to bear. Through Him, we are grafted into the olive tree (Romans 11:17–24). We are called to abide in the Vine and bear fruit that remains (John 15:5–8). God still inspects the fruit of His vineyard. Are we walking in the Spirit, reflecting the justice and righteousness of our Messiah?
V 26-30 How would judgment come? God would whistle for Assyria and other nations. Nations that normally ignored Israel’s God as insignificant would respond swiftly. They would resemble hungry lions on the prowl for whatever prey they could find. The sounds and fury of warfare would be heard throughout the land. Hope had vanished for that generation who failed to distinguish between light and darkness would now experience only darkness. Storm clouds hung over all of life.
In spite of God’s blessing on his people, they ignored and rejected him. The result was a people blind to reality, unable to judge between good and evil, light and darkness, sweet and bitter. The people of the Book ridicule God, his plans, and his demands. They made their own laws to fit their own desires. God said, enough! Time for judgment. Darkness is all you will see. King of Assyria: come My people are yours for the taking.
