Robbing the Poor
Any harm done to a poor person is especially cruel because his suffering is amplified by his poverty. Most people can make do even if robbed, but when a poor man is robbed, he is left without resources.
Crowded places, such as the city gates are unpleasant for everyone, but they can be especially difficult for poor people. Therefore, one should make an extra effort to help poor people overcome the embarrassing conditions in such places.
אַל תִּגְזָל דָּל כִּי דַל הוּא וְאַל תְּדַכֵּא עָנִי בַשָּׁעַר
(22) Don’t rob the pauper. His suffering is greater because he is poor,
and do not crowd the pauper at the gate.
This proverb encourages us to make extra allowances for the difficulties faced by the poor. That means being careful not to deprive a poor person of his property and not to deprive him of the space he needs to be comfortable.
(22) Don’t rob the pauper — אַל תִּגְזָל דָּל
because of his poverty, — כִּי דַל הוּא
that increases his suffering.
Don’t crowd the poor — עָנִי וְאַל תְּדַכֵּא
at the gate where they suffer more. —בַשָּׁעַר
 Don’t be tempted by the weakness of the poor to rob them. Hashem will protect them from depredation. (רש”י)
 Don’t be tempted to rob the poor, thinking that Hashem wants them to be poor. (חבל נחלה).
 The gate may be a reference to the courts of justice, which typically met in the gates of the city. The judge is forbidden from discriminating against the poor (דעת סופרים).
 The reference to the city gate suggests that one must be careful not to embarrass a poor man in public. (רבינו יונה).
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