30 – The Mitzvah of Lending / Chapter four
C. Although we have explained that the mitzvah of chessedextends even to a person whom one hates, including someone upon whom there is a mitzvah to hate, nevertheless there is a difference between these cases. In a situation where two people approach someone with a request for a favor and one of them is a person whom he loves while the other is a person he hates, then the rule is this: If he hates that person without justification, then it is a mitzvah to help the hated one first, in order to subdue his [the benefactor’s] Yetzer Ha’ra (despite the fact that this will prevent him from helping the one he loves). But if he hates that person because of a sin that that person had committed, it is mitzvah to first help the good person, whom he loves, before helping the improper person who committed the sin.