In this week’s parsha we have the mitzvah of tzedokah, the pasuk which teaches us this mitzvah ends with enigmatic command to give the poor person: די מחסרו אשר יחסר לו - “that which is lacking to him”. Rashi briefly explains, based on a Gemara (Kesubos 67b), that this teaches that one must even give the poor person a horse to ride on and a servant to run in front of it.
The Gemara elaborates that normally one does not need to give a poor person so much money that he will become rich, rather one should provide him with what he is lacking, such as basic needs. However, in the case of a person who was wealthy and then lost all of his wealth, the Torah is teaching that one must provide for him those things that he feels lacking now when compared to when he was wealthy.
