What does Psalm 37:21 mean?
ESV: The wicked borrows but does not pay back, but the righteous is generous and gives;
NIV: The wicked borrow and do not repay, but the righteous give generously;
NASB: The wicked borrows and does not pay back, But the righteous is gracious and gives.
CSB: The wicked person borrows and does not repay, but the righteous one is gracious and giving.
NLT: The wicked borrow and never repay, but the godly are generous givers.
KJV: The wicked borroweth, and payeth not again: but the righteous sheweth mercy, and giveth.
NKJV: The wicked borrows and does not repay, But the righteous shows mercy and gives.
Verse Commentary:
One of the distinguishing marks of a wicked person is his lack of trustworthiness. This is symbolized by David as a person who borrows but does not pay back what is owed. In contrast, a righteous person not only meets their obligations, they practice generosity. Sin leads a person to selfishly take from others; godliness encourages charity and kindness.

The righteous have what they need, because God blesses them, and therefore they can give to others. God promised to reward Israel's faithfulness by making it possible for the Israelites to lend to many nations (Deuteronomy 15:6). He repeated this promise in Deuteronomy 28:12. So far as literal material prosperity is concerned, this promise does not extend to every believer in every period of history. It was given to the nation of Israel and was conditioned on Israel's faithfulness to the Lord. It is, therefore, a generalization, as is much of the advice in the book of Proverbs.

However, verses such as this show clearly that God frowns on untrustworthiness but smiles on generosity. Second Corinthians 9:11 teaches us that God enriches us for a reason: so that we may be generous in every way.
Verse Context:
Psalm 37:21–31 points out the blessings of the righteous. David describes not only their blessings but also their character and conduct. The Lord blesses the righteous with the promise of an inheritance, personal guidance, protection, provision, a good posterity, and His presence.
Chapter Summary:
In this psalm, David contrasts the way God protects and saves His people, contrasted with the ruin which awaits the wicked. Much of this seems to be based on David's own experiences (Psalm 37:25, 35). As with many other passages in Psalms and Proverbs, this passage encourages godly wisdom. Those who reject God and His ways can expect uncertainty on earth and disaster in eternity.
Chapter Context:
Psalm 37 lies in the first division of Psalms and addresses mankind. Its tone resembles that of the book of Proverbs. The psalm dispenses wisdom about the security of the righteous man and the insecurity and fate of the wicked man. Psalms 36 and 39 also describe the insecurity and fate of the wicked. The covenant God made with Israel in Leviticus 26 and Deuteronomy 27—30 is the basis for David's assurance that the righteous are secure. The issue of the prosperity of the wicked is also featured in Psalms 49 and 73. David most likely wrote Psalm 37 in his old age.
Book Summary:
The book of Psalms is composed of individual songs, hymns, or poems, each of which is a ''Psalm'' in and of itself. These works contain a wide variety of themes. Some Psalms focus on praising and worshipping God. Others cry out in anguish over the pain of life. Still other Psalms look forward to the coming of the Messiah. While some Psalms are related, each has its own historical and biblical context.
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