What does Proverbs 28:27 mean?

Generosity reflects a godly spirit (Proverbs 14:21; 19:17) which is associated with better chances of earthly success (Proverbs 11:24; 28:25). Other proverbs note that those who properly care for the weak and needy are following God's will (Proverbs 14:31). This is one reason that those who are generous are more likely to succeed than those who are entitled and stingy (Proverbs 11:24; 28:22). This is contrasted with those who claim they didn't know about the needs of others, when they're simply choosing to look the other way (Proverbs 21:13; 24:11–12). The Lord and men look favorably on those who are giving, but greedy people are looked down on by both (Proverbs 11:26; 28:3).

In the Law God gave to Israel, He told farmers not to harvest fields right up to the edge or strip their vineyards bare. They were to leave some of the wheat and the fallen grapes for the poor and those travelling (Leviticus 19:9–10). When Naomi returned from Moab to Bethlehem, she was a widow, and was accompanied by her widowed daughter-in-law Ruth. Naomi had a relative of her late husband who was a righteous man. His name was Boaz, and he was a farmer. He was also very generous. Seeing Ruth following the reapers in his field and gleaning after them, Boaz instructed his reapers to let Ruth follow behind them to get the most possible grain. He also provided her with water and food (Ruth 2).