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Whoever despises his neighbor is a sinner, but blessed is he who is generous to the poor (Proverbs 14:21, ESV). Those who are of shallow substance, those who have a quality of character that is as deep as half-inch rain’s mud puddle are the quickest to lose interest in the well-being of another, especially one who is poor. In fact, as the Lord looks at it, there is no way that such a person can be saved in that state of mind. It is a state of mind that lacks love. How does one love another if there is no interest in the other person? On the other hand, those who are generous in their material goods are in great position to be generous in their words that are full of love and teaching. All this for a great purpose.
etsop95 
This is a great passage on human relations. More specifically with reference to how one treats and thinks of the poor (a common Biblical theme)
Clearly complimentary to the previous verse; in fact v21 seems to me to be a direct commentary on v 20. The context of the first phrase in v 21 is “sandwiched” between references to how one treats the poor in v 20: “the poor is hated even of his own neighbor” and v 21: “he that hath mercy on the poor happy is he”. Thus the general context is that of the treatment of the poor.
Note the warning regarding “despising your neighbor (poor? see above); and compare with the words of James the Just regarding such in his NT letter (James 2:5-8)
How one thinks of and treats the poor (the latter being subsequent to the former) is a common Bible theme, and thus apparently a common issue among the Hebrew people of that time. In this regard, there would seem to be a lesson for all peoples of all times of all cultures; ours certainly being no exception and perhaps even a prime example.
For as the bible says “the poor will never cease out of the land” (Deut 15:11). Since such seems to always be the case, then the matter of how one thinks of and treats the poor will always be a matter of practical importance. James the Just even ties the matter into whether one fulfills what he calls the royal law: “Thou shalt love thy neighbor as thyself”
Appreciate your thoughts, Dave