The whole of Isaiah is a prophetic book. The summary of the entire book can be found in the first chapter:

Isa 1:19 If you are willing and obedient, You shall eat the good of the land;
Isa 1:20 But if you refuse and rebel, You shall be devoured by the sword”; For the mouth of the LORD has spoken.

At its core, the book of Isaiah is a call for repentance from Israel. This repentance is coupled with strong threats of annihilation in the case of unbelief and strong promises of blessings in exchange for righteousness. The book was not written for future generations, although the themes are eternal. The book was written to warn and predict that the current generation would experience the events that are depicted. Within the book, there is a shift from pre-exile to an exile frame of reference. The people to whom the book was written experienced judgment in their own lifetimes.

A strong theme in Isaiah is repentance. There is always room for Israel to repent, as explicit in the many and scattered calls for repentance throughout the book of Isaiah. It is in this context that God prophesies destruction.

In Isaiah 5, God begins building an illustration of His experiences and present relationship with Israel:

Isa 5:1 Now let me sing to my Well-beloved A song of my Beloved regarding His vineyard: My Well-beloved has a vineyard On a very fruitful hill.
Isa 5:2 He dug it up and cleared out its stones, And planted it with the choicest vine. He built a tower in its midst, And also made a winepress in it; So He expected it to bring forth good grapes, But it brought forth wild grapes.

So here is the scenario so far: a vineyard planter has a vineyard. He engages in all the correct horticulture techniques and then expects good produce. Additionally, the vineyard owner constructs a winepress because he expects to be able to make wine from these good grapes. In the illustration, the vineyard owner has done everything conceivable to produce good grapes. The vineyard planner expected good grapes but the result was wild grapes.

In the middle of the illustration, God shifts the frame of reference to Himself. He is the vineyard owner and Israel is the vineyard:

Isa 5:3 “And now, O inhabitants of Jerusalem and men of Judah, Judge, please, between Me and My vineyard.
Isa 5:4 What more could have been done to My vineyard That I have not done in it? Why then, when I expected it to bring forth good grapes, Did it bring forth wild grapes?

God challenges Israel to offer up additional things that He could have done for His vineyard. The question is rhetorical. The rhetorical answer is “nothing”. God did all that is possible to produce good fruit. God finishes by explaining that He expected good, but His expectations did not happen as planned. This is paralleled to the vineyard owner expecting good grapes but instead getting wild grapes.

The illustration continues:

Isa 5:5 And now, please let Me tell you what I will do to My vineyard: I will take away its hedge, and it shall be burned; And break down its wall, and it shall be trampled down.
Isa 5:6 I will lay it waste; It shall not be pruned or dug, But there shall come up briers and thorns. I will also command the clouds That they rain no rain on it.”
Isa 5:7 For the vineyard of the LORD of hosts is the house of Israel, And the men of Judah are His pleasant plant. He looked for justice, but behold, oppression; For righteousness, but behold, a cry for help.

The illustration concludes with a dire warning: God will destroy His vineyard. The vineyard planter expected good grapes that never materialized, and thus God will utterly destroy Israel. Explicitly, God explains that the Vineyard was Israel and the plants were the people. God expected justice, but got oppression. God expected righteousness, but got notifications of wickedness (this could be the prayer of the oppressed or third party reports of evil).

The Augustinian Christian will not want to take this parable at face value. In the parable, God attempts to create something that does not materialize. God had expected it to materialize, but it never does materialize. God repents from building up Israel to destroying Israel. The furious anger radiates from the text.

Augustinians try to rationalize this away. From Contending with Christianity’s Critics:

If I tell a group of grade-school boys that I expect them to behave, does this show that I believe they will behave? Not at all. I may, at the same time as I expect them to obey, also believe that they will fall short of my expectations. (I’ve had experience with this particular group before!) If God expected grapes in this sense, His expectation provides no evidence whatsoever that He didn’t also foreknow that the vineyard would yield wild grapes instead.

But this rationalization does not fit on multiple levels.

1. It does not fit the illustration. The vineyard planter did everything correct to grow good grapes. The vineyard planter had not anticipated bad grapes. He even goes so far as building a wine press. No vineyard planter would go through all the planting and building process while knowing there would be no produce. To say that the vineyard owner expected wild grapes defeats the entire point of the illustration: that Israel rebelled although God did more than enough to convince Himself (and reasonable third parties) that Israel would be righteous.

2. The story is not about expectations (standards). This story is about failed attempts to shape future events. The vineyard owner sets up the vineyard (Israel) to produce good grapes (righteous people), yet wild grapes (evil people) are the result.

3. God responds by destroying Israel utterly. The reaction is vitriol. If this story was about failed standards that were expected, angry slaughter would not be a fitting result. If God knew that Israel would reject Him, this is how the illustration would read:

A vineyard owner builds a vineyard, walls, a tower and winepress knowing full well none were needed and none would be used. Furthermore, the vineyard owner builds and plants knowing full well that he will have to destroy absolutely everything he created. After the vineyard does not produce, the vineyard owner destroys everything.

This is a psychotic story and is totally contrary to the point that Isaiah is trying to make. The natural reading is that God is dismayed, angered, and retaliates against something He attempted to avert and subsequently did not expect.

Isa 5:8 Woe to those who join house to house; They add field to field, Till there is no place Where they may dwell alone in the midst of the land!

This verse seems to single out greed as a primary sin of Israel. The verse is a warning against those who want to acquire every piece of land such that there is no place left for others and the greedy individual is alone the sole ruler. The proper punctuation seems to be: “Woe to those who join house to house. They add field to field [un]till there is no place. Where they may dwell alone in the midst of the land!”

The subsequent threat God gives applies extra strong against those acquiring land for wealth:

Isa 5:9 In my hearing the LORD of hosts said, “Truly, many houses shall be desolate, Great and beautiful ones, without inhabitant.
Isa 5:10 For ten acres of vineyard shall yield one bath, And a homer of seed shall yield one ephah.”

The rich will buy up land, but not gain the wealth that would be normally expected by the land. This parallels the parable in the first few verses where God experienced the same in planting Israel. Whereas God did not gain His expected produce, those who own land will also fall short. From verse 10, land owners would lose over 90% of their seed investment, not counting the lost labor, material, and time for growing. This curse seems very retaliatory against Israel.

Isa 5:11 Woe to those who rise early in the morning, That they may follow intoxicating drink; Who continue until night, till wine inflames them!
Isa 5:12 The harp and the strings, The tambourine and flute, And wine are in their feasts; But they do not regard the work of the LORD, Nor consider the operation of His hands.

This warning is against drunkards, against people who wake up early to begin drinking and then continue deep into the night. This also fits the vineyard theme. Part of the woe, logically following from the previous verse, will be that their wine will stop being produced. These people listen to music for entertainment, but forget to give God His due regard for His power.

Isa 5:13 Therefore my people have gone into captivity, Because they have no knowledge; Their honorable men are famished, And their multitude dried up with thirst.
Isa 5:14 Therefore Sheol has enlarged itself And opened its mouth beyond measure; Their glory and their multitude and their pomp, And he who is jubilant, shall descend into it.
Isa 5:15 People shall be brought down, Each man shall be humbled, And the eyes of the lofty shall be humbled.

Verse 13 seems to be a prediction, despite the English translated tenses. At this point neither the Assyrian (Israel) nor Babylonian (Judah) exiles had taken place. The people are warned that their wine will be gone (note that the previous verse was against drunkards and the verses before that were against vineyard owners). Additionally, people will die (Sheol is synonymous with “the grave” in the Old Testament): the drunkards, the partiers, and the greedy (also in reference to the previous verses). In this way, their fortunes will be reversed. They were once full of life and riches, but now they will be killed and humbled.

Isa 5:16 But the LORD of hosts shall be exalted in judgment, And God who is holy shall be hallowed in righteousness.
Isa 5:17 Then the lambs shall feed in their pasture, And in the waste places of the fat ones strangers shall eat.

The reader is to understand that judgment of these individuals (the greedy land-grabbers, the drunkards, and the partiers) is on face value a righteous act. Punishing of these people is seen as exalting God and a righteous act. Their property will go to waste (lambs will feed on the weeds) and strangers will own the land. The land-grabbers, drunkards, and partiers are called the “fat ones”. Being fat is an outward sign of these things.

Isa 5:18 Woe to those who draw iniquity with cords of vanity, And sin as if with a cart rope;
Isa 5:19 That say, “Let Him make speed and hasten His work, That we may see it; And let the counsel of the Holy One of Israel draw near and come, That we may know it.”

This next part of Isaiah is an expansion of the list of evil people upon who judgment will be made or a further characterization of the same. These people actively seek sin. The illustration is that they build ropes and pull their sin behind them on a cart. This is prideful and willful sin, not passive and accidental sin. These people question God’s judgment and/or blessings, asking when they will see them. The picture this paints of Israel is one in which God’s prophets are not taken seriously. The people might have been warned in the past and never experienced judgment. They are skeptical of the prophecies.

Isa 5:20 Woe to those who call evil good, and good evil; Who put darkness for light, and light for darkness; Who put bitter for sweet, and sweet for bitter!

Verse 20 appears to be repetition to emphasize the point. Calling evil good and good evil is reiterated in three different ways with three different word sets. People are not dealing with literal light or darkness, or even actual sweet and bitter tastes. Those words are a flowery way of saying people are mislabeling good and evil.

This verse is important for illustrating the figurative uses of light and darkness. Compare to Isaiah 45:

Isa 45:7 I form the light, and create darkness: I make peace, and create evil: I the LORD do all these things.

God is not saying that He literally creates literal light and darkness, although the author would probably not deny that statement. The verse is about God giving both judgment and blessings. Light and darkness are very figuratively loaded words and are normally used in a non-literal sense.

Isa 5:21 Woe to those who are wise in their own eyes, And prudent in their own sight!
Isa 5:22 Woe to men mighty at drinking wine, Woe to men valiant for mixing intoxicating drink,
Isa 5:23 Who justify the wicked for a bribe, And take away justice from the righteous man!

Notice the theme of pride. These people claim God’s punishments and blessings will not happen. These people claim evil as good and good as evil. They pride themselves in the here and now: parties, riches, drinking, and a life without God. They exchange injustice for money, oppressing the innocent. God will humble them:

Isa 5:24 Therefore, as the fire devours the stubble, And the flame consumes the chaff, So their root will be as rottenness, And their blossom will ascend like dust; Because they have rejected the law of the LORD of hosts, And despised the word of the Holy One of Israel.
Isa 5:25 Therefore the anger of the LORD is aroused against His people; He has stretched out His hand against them And stricken them, And the hills trembled. Their carcasses were as refuse in the midst of the streets. For all this His anger is not turned away, But His hand is stretched out still.

Notice again the vineyard or farming references. God planted the vineyard; no good fruit was produced, so God will burn it down. God’s anger is aroused. God is stirred to action because they “rejected the law of the Lord”. God will kill them. The imagery is dead bodies strewn throughout the streets. The phrase is written as if it is past tense, but it might yet be predictions of the future as with verse 13. Another possibility is that there may have been some unnamed past event that both this and verse 13 describes.

Isa 5:26 He will lift up a banner to the nations from afar, And will whistle to them from the end of the earth; Surely they shall come with speed, swiftly.

This whistling theme runs through Isaiah. This is how God gets foreign people to accomplish His will; he entices them. Compare:

Isa 7:18 And it shall come to pass in that day That the LORD will whistle for the fly That is in the farthest part of the rivers of Egypt, And for the bee that is in the land of Assyria.

The general enticement is usually in the form of wealth. Evil people see the riches of Israel and plot against Israel. This is recorded to have happened in 2 Kings 20 when Babylon sees the riches of Israel and reports back to their nation. Similarly, the Assyrians were paid in silver by Israel for mercenary work (2Ki 16:8), this might have made them believe Israel was ripe for taking. God uses these enticements to accomplish His plans, although not letting the evil people live without judgment (see Isaiah 10:12).

Isa 5:27 No one will be weary or stumble among them, No one will slumber or sleep; Nor will the belt on their loins be loosed, Nor the strap of their sandals be broken;
Isa 5:28 Whose arrows are sharp, And all their bows bent; Their horses’ hooves will seem like flint, And their wheels like a whirlwind.
Isa 5:29 Their roaring will be like a lion, They will roar like young lions; Yes, they will roar And lay hold of the prey; They will carry it away safely, And no one will deliver.

This illustration is that the call to Israel’s enemies will bring rapid response. The enemy will not rest until they take Israel. They will not sleep or even remove their weapons until they have victory. Victory will be unstoppable and swift. This passage would most likely refer to the Assyrians, as the Assyrian captivity came shortly after.

Isa 5:30 In that day they will roar against them Like the roaring of the sea. And if one looks to the land, Behold, darkness and sorrow; And the light is darkened by the clouds.

Again, darkness and light are used in a metaphorical sense. When Israel is destroyed, Israel is in “darkness”. The “light” is shut out, as Israel is left without hope and mourns for the dead.