What does Proverbs 14:21 mean?
ESV: Whoever despises his neighbor is a sinner, but blessed is he who is generous to the poor.
NIV: It is a sin to despise one's neighbor, but blessed is the one who is kind to the needy.
NASB: One who despises his neighbor sins, But one who is gracious to the poor is blessed.
CSB: The one who despises his neighbor sins, but whoever shows kindness to the poor will be happy.
NLT: It is a sin to belittle one’s neighbor; blessed are those who help the poor.
KJV: He that despiseth his neighbour sinneth: but he that hath mercy on the poor, happy is he.
NKJV: He who despises his neighbor sins; But he who has mercy on the poor, happy is he.
Verse Commentary:
Unlike most other works of Scripture, individual statements in the book of Proverbs are often meant to stand alone. That does not mean context never applies. In this case, the neighbor being mentioned is likely the same referred to in the prior verse (Proverbs 14:20). The two statements together imply that it is a serious sin to favor the rich while mistreating those who are poor.

Both pride and stinginess are part of the sin depicted, but hatred may be included also. God made provision in the Law for the care of poor people (Exodus 23:11; Leviticus 19:15; 23:22; Deuteronomy 15:7–8). The word rendered "despises" here is from a root word literally meaning "to show contempt" or "to belittle." Those who sneer at the poor or fail to care for them sin against the Lord.

The flip side of this issue is the blessing the Lord pronounces on those who show generosity to the poor. The New Testament includes a story of a rich man and a poor beggar. The rich man could have shown kindness and generosity to the beggar, but he didn't. The beggar had to try to satisfy his hunger by eating scraps from the rich man's table. The situation differed, however, in eternity. The beggar enjoyed blissful comfort, whereas the rich man was in torment and longed to have a drop of water placed on his tongue (Luke 16:19–31). The point of that parable is not that a person's eternal destiny depends on how they treat the poor. Rather, it's that earthly wealth is not a sign of moral conduct.

In the case of this verse from Proverbs, it's true that those who are generous to the poor frequently benefit from their own generosity. Their reputation and influence can be enhanced, and along with that their own success.
Verse Context:
Proverbs 14:15–35 continues Solomon's wise sayings, once again mostly contrasting the wicked and the upright. He points out that those who do evil, by rejecting God's wisdom (Proverbs 1:7) are foolish and have no security. Those who do God's will (Proverbs 3:5) are wise and have unfailing security.
Chapter Summary:
This continues a series of literal "proverbs:" short statements of general-case wisdom. The first ten verses of this chapter contrast positive and negative traits related to work ethic, self-control, and seeking wisdom. Then come several verses contrasting the fate of the righteous with that of the wicked. The rest of this passage provides statements on a broad range of subjects.
Chapter Context:
Proverbs 14 continues King Solomon's wise sayings. In this chapter he discusses a variety of topics such as wisdom and folly, honesty and dishonesty, righteousness and evil, national security and national disgrace, personal security and destruction, the fear of the Lord, generosity, and wise servanthood. This series of astute comments will continue for several more chapters.
Book Summary:
Proverbs is best understood in context with the books of Ecclesiastes and Job. In Proverbs, “wisdom” is given in short, simple, general terms. Ecclesiastes represents wisdom based on observation and experience. This often shows how the general principles of the book of Proverbs don’t apply in absolutely every circumstance. Job represents wisdom based on the experience of suffering and injustice. All three come to the conclusion that God does indeed know best, and the most sensible course of action is to follow His will.
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