In Yore De’ah 249:3, the Mechaber cites the halacha that one must give tzedakah, charity, with a smile, with joy and good-heartedly. When there is a poor person, one should empathize with him in his struggles and one should speak to him with words of consolation and comfort. If he gave the tzedakah in a negative or mean manner – he lost his zchus.
But what is when one gives the tzedakah not to an ani, athe poor person himself, but rather through a Gabbai? Do these Halachos still apply?
Rav Chaim zt”l answered that he must be careful in these matters even when dealing with a Gabbai, and not just the poor person himself.
In Rav Chaim’s Derech Emunah (BH “B’aitzev in Siman 249) in his recitation of the position of the Ri Korkos, the wording is “he gives it with a sad face” – which indicates that the issue is also if one only deals with the Gabbai. This is the focus is on the giver’s own sadness. It is interesting to note as well that Rav Yoseph Karo changes the language of the Rambam in Matanos Aniyim 10:4. The Mechaber leaves out the word “ani.”