28:1: The wicked flee when no one pursues, But the righteous are bold as a lion.
This proverb is structured chiastically with “wicked” and “righteous” in the center:
When no one pursues
Like a lion
This structure is designed to make the contrast explicit at every point. In every way, they are different.
The point seems to be that all the difference is really in the moral qualities. Righteousness results in boldness and wickedness results in cowardice. It also suggests that the righteous are pursuers while the wicked are the pursued. The righteous are likened to a lion, a beast that hunts for prey. But the Proverb says that the wicked run away even when no one is pursuing. The proverb suggests that the righteous will be perceived as a threat by the wicked and the wicked will act in fear even when there is no danger. The proverb says that the righteousness of the righteous is really boldness, but the wicked see only a predator, a fierce lion on the loose. There is also an implicit comparison of fear. The righteous fear the Lord and are therefore bold, but because the wicked do not fear the Lord they are fearful. Fearing God means we have no fear of man. Conversely refusing to fear the Lord is a guarantee that we will fear men. Waltke also points out that there is good objective reason for this fear and lack of fear. The promises of God surround the righteous, but only warnings of punishment and disaster surround the wicked. In one sense their fear is unfounded (“no one pursues”), but on a deeper level it is actually very well founded. Living antagonistically with the King/Lion who rules the world is never safe.
28:2: Because of the transgression of a land, many are its princes; but by a man of understanding and knowledge right will be prolonged.
The parallels here are as follows:
In the transgression of the land
Many are its princes
In a man [ADAM] of understanding and knowledge
The right will long continue
The parallel sets up a contrast between “transgression” and an “Adam.” With the contrast in mind, we might think of “transgression of the land” as something like Adam’s first sin. The contrast is even stronger when we note that this Adam has understanding and knowledge which is what the original sin focused on, the tree of knowledge and the question of whether it would make one wise and give understanding. There is also the parallel between the “land” and “ADAM(AH).” A man is a sort of ground which can have produce, fruit grows out of it. A land full of transgression grows and multiplies princes. The implication is that princes are a sort of weed, a curse on the sins of the land. On the other hand where the soil is mixed with understanding and knowledge, right is maintained.
The political statement seems to be that where a people is unlawful, laws and law enforcers multiply, but where wisdom and prudence characterize a people, righteousness is maintained. Given the implied contrast, we assume that this righteousness is without many rulers. People know what is right and they do it without having to be forced or without enforcing what is right, i.e. its princes are few and do their jobs well. It may also be implied that the multiplication of princes is a futile attempt at dealing with transgressions. Many princes is not the same thing as righteousness being maintained, but in the implication is that princes were not doing their jobs well and so the burden of the transgressions can justly rest on weak rulers as well. The proverb says that only understanding and knowledge can produce sustainable justice. Remembering that Proverbs is written to a prince or perhaps multiple princes makes this a pointed warning to the original audience.
28:3: A poor man who oppresses the poor is like a driving rain which leaves no food.
The obvious point seems to be that rain ought to be a source of nourishment for crops. A poor man ought to understand the plight of a fellow poor person. The word for man often has connotations of strength. So this is a weak-strong-guy which is an oxymoron. And this weak-strong-guy is oppressing the poor apparently with his strength. The weak-strong-guy is probably a leader who has had some misfortune befall him. He’s had a bad year; there’s a recession, etc. And he grasps at what the poor-diligent have produced. This weak-strong-guy (leader) parallels that “driving” rain, the rain that is meant for nourishment has become a source of ruin. Literally the “driving” rain is a “prostrate” rain, a rain that lies down (Jer. 46:15). This highlights the oppression as a sort of laziness. Perhaps it also suggests a foolish impatience: ie. If I dump a lot of water on my plant right now, maybe it will grow faster. But overwatering is a good way to kill crops too. The final thought is: “there is no bread.” And this is ambiguous enough to cover a specific instance of oppression as well as broader national policies in any given land. There is a way of pouring resources into a land that is actually a form of oppress and results in less food for everyone.
28:4 Those who forsake the law praise the wicked, but such as keep the law contend with them.
This proverb is about antithesis. It describes those who have the law (Torah) and then abandon it and thereby align themselves with the wicked. And it describes those who guard the law (Torah) and thereby fight against the wicked. We are either for God and for His people or we are against the Lord and against His people.
Lawlessness is itself a compliment to the wicked. It praises them. It is also compliment because it is imitation. It also praises the wicked as an encouragement to be wicked, setting the apostate up as an proof of their pseudo-wisdom.
Conversely, Torah-keeping is a kind of warfare. This parallels 28:1 somewhat where the righteous are bold like lions and threaten the “wicked.” While in one sense the righteous are not a real threat to the wicked (in the way they think of a threat), in other sense the righteous are always a threat to their way of life. The righteous keep Torah, and that will always create contention and warfare with the wicked.
28:5:Evil men do not understand justice, but those who seek the Lord understand all.
Here the proverbs return to the necessity of having “understanding.” An Adam of understanding prolongs justice (28:2), but here evil guarantees the lack of understanding. And specifically, it is no understanding of judgment. And the contrast is radical: those who are seeking YHWH understand everything. The comparison may also be in the “seeking.” Evil from earlier in Proverbs are looking for evil to do, plotting to do wickedly. The only other option is to plot righteousness, seeking Yahweh. And the promise is that in the seeking, understanding will come. But we do not understand in order to seek; we seek in order to understand.