| Gill's Exposition of the Entire Bible Better it is to be of an humble spirit with the lowly,.... The followers of the meek and lowly Jesus, whose spirits are humbled under a sense of sin; have mean thoughts of themselves and their own righteousness, and submit to the righteousness of the Son of God, and wholly trust in him for salvation; and ascribe all they have and are to the free grace of God; humble themselves under the mighty hand of God; are resigned to his will, and patiently bear all afflictions without murmuring, and think better of others than themselves: these are not in so much danger of falling as the proud and haughty, and are more grateful to men, and acceptable to God; with these he vouchsafes to dwell; to these he gives more grace, and they shall inherit the earth. Wherefore it is better to be of such a spirit, and be ranked among and keep company with the meek and lowly, than to divide the spoil with the proud; the spoils of the poor with proud oppressors; or spoils gotten in war with proud and ambitious princes; or the spoils of kingdoms and states with antichrist, divided by him among his proud followers: it is better to be the followers of Christ, and have but little, than to be his, and have ever so much.
Keil and Delitzsch Biblical Commentary on the Old Testament19 Better in humility to dwell among sufferers, Than to divide spoil among the proud. The form שׁפל is here not adj. as Proverbs 29:23 (from שׁפל, like חסר, Proverbs 6:32, from חסר), but inf. (like Ecclesiastes 12:14, and חסר, defectio, 10:21). There existed here also no proper reason for changing עניּים (Chethı̂b) into ענוים; Hitzig is right in saying that עני may also be taken in the sense of ענו [the idea "sufferer" is that which mediates], and that here the inward fact of humility and the outward of dividing spoil, stand opposed to one another. It is better to live lowly, i.e., with a mind devoid of earthly pride (Demut [humility] comes from do with the deep e, diu, servant), among men who have experience of the vanity of earthly joys, than, intoxicated with pride, to enjoy oneself amid worldly wealth and greatness (cf. Isaiah 9:2).
Geneva Study BibleBetter it is to be of an humble spirit with the lowly, than to divide the spoil with the proud.
Jamieson-Fausset-Brown Bible Commentary19. divide the spoil-that is, conquer. Avoid the society of the proud (Jas 4:6).
Matthew Henry's Concise Commentary16:12. The ruler that uses his power aright, will find that to be his best security. 13. Put those in power who know how to speak to the purpose. 14,15. Those are fools, who, to obtain the favour of an earthly prince, throw themselves out of God's favour. 16. There is joy and satisfaction of spirit, only in getting wisdom. 17. A sincerely religious man keeps at a distance from every appearance of evil. Happy is the man that walks in Christ, and is led by the Spirit of Christ. 18. When men defy God's judgments, and think themselves far from them, it is a sign they are at the door. Let us not fear the pride of others, but fear pride in ourselves. 19. Humility, though it exposes to contempt in the world, is much better than high-spiritedness, which makes God an enemy. He that understands God's word shall find good. 21. The man whose wisdom dwells in his heart, will be found more truly prudent than many who possess shining talents. 22. As waters to a thirsty land, so is a wise man to his friends and neighbours. 23. The wise man's self-knowledge, always suggests something proper to be spoken to others. 24. The word of God cures the diseases that weaken our souls. 25. This is caution to all, to take heed of deceiving themselves as to their souls. 26. We must labour for the meat which endureth to everlasting life, or we must perish.
Matthew Henry's Whole Bible CommentaryVerse 19 This is a paradox which the children of this world cannot understand and will not subscribe to, that it is better to be poor and humble than to be rich and proud. 1. Those that divide the spoil are commonly proud; they value themselves and despise others, and their mind rises with their condition; those therefore that are rich in this world have need to be charged that they be not high-minded, 1 Tim. 6:17. Those that are proud and will put forth themselves, that thrust, and shove, and scramble, for preferment, are the men that commonly divide the spoil and share it among them; they have the world at will and the ball at their foot. 2. It is upon all accounts better to take our lot with those whose condition is low, and their minds brought to it, than to covet and aim to make a figure and a bustle in the world. Humility, though it should expose us to contempt in the world, yet while it recommends us to the favour of God, qualifies us for his gracious visits, prepares us for his glory, secures us from many temptations, and preserves the quiet and repose of our own souls, is much better than that high-spiritedness which, though it carry away the honour and wealth of the world, makes God a man's enemy and the devil his master. | 
