Humility is something to be embraced by God's people. It is not usually considered a great thing because often to be humble means that you will not be on the top rung of things. Here where Solomon tells us it would be better to be humble in spirit with the lowly that truth comes out. The humble man is the one who is to embrace a low social position. The humble man does not seek great things for himself. The sense of this Hebrew word is that one is not only humble, but they are also meek (strength under control) and they are contrite (they know their sin and greive over it. The humble also associate with a group most people would shun - the lowly. The lowly are those who are poor, afflicted, and usually crying out for help to the Lord. These people are often absued by the rich and by oppressive leaders. When you associate with such people, it means that you most likely will not be among the movers and shakers of society. Yet it is better to be here among the lowest of the low than to be with those who suffer from pride. Something that will prove helpful in understanding the second part of this proverb is the reality that the humble are not seeking advancement for themselves. They serve God and look to Him for their advancement and their victories.
We are warned that it is better to be with the lowly and to be humble with them - than to divide the spoil with the proud. The proud (Hebrew word "ge'eh") are not just proud and haughty - they are those whose pride is bringing the Lord Himself to a point of desiring to judge them. Granted, they are getting the spoil - which meant money and things - but at what cost? The idea of spoil means that they are fighting or warring against another. The spoil was what was left over after they had wiped out their enemies. The proud conquer their opposition, and then rise up and take their stuff afterwards. Their advancement does not come by trusting the Lord - but by dominating and destroying their competition. They leave in their wake a large number of people who are either ruined or are so dominated that they surrender what is theirs to their conquerors. True, they may have a lot of money, a lot of stuff, and victories to their credit - but they also have God as their adversary. God watches all this and burns with anger - responding to their pride and arrogance by promising a recompense that may not come today - but it is surely coming. When you consider this, seeing that even though they have victories and spoils, they come at far too high a price, the judgment of God - you also see why it is better to be with the humble and even oppressed than with this crew who are one day going to face the wrath of God.