When a fur coat isn't enough.
Re'eh The holy Reb Simcha Bunim of Peshischa stopped in the town of Sheps on his way home from a trip. He sought out a local chossid, Reb Zalman, who was both pious and poverty-stricken, handed him a large sum of money, and asked him to prepare the customary meal for himself and his chassidim. The sum far exceeded the cost of the meal. Later, Reb Simcha handed his host additional money to purchase a fur coat and new clothes for Reb Zalman, and when he heard that Reb Zalman’s wife and children also wore rags, he added more money for their wardrobes too. After the meal, Reb Simcha gave Reb Zalman yet another handsome sum of money to buy drinks, and again there was money left over. Later, Reb Simcha summoned Reb Zalman and handed him still another large sum of money, but the chossid objected. “How could I?” he protested. “The Rebbe has already given me so much; I still have plenty left from all the shopping!”
“In Parshah Re’eh, we read about giving tzedakah,” Reb Simcha Bunim explained. “You shall surely give him, and your heart shall not be grieved when you give to him.” Why would a Jew be grieved by giving tzedakah? The Torah is teaching us the true meaning of the mitzvah. “I couldn’t tolerate seeing your poverty, nor could I bear knowing that you and your family have nothing but rags to wear. The money I gave you was not because there’s a mitzvah of tzedakah, it was to soothe my own conscience. My heart was grieved by your plight. But now that you have the basic necessities and my heart is settled, I can finally give you something to fulfill Hashem’s mitzvah rather than to satisfy my own need for comfort.” Spiritual Tzedakah On a more subtle level, perhaps this can also apply to spiritual tzedakah. For many years a woman had a Torah-study partner, until one day her partner let her know that she would be dropping her for a “better candidate,” since she hadn’t yet become religious as a result of their learning. “I was so hurt,” she confided. “I realized that my life and my journey weren’t important to her. She just wanted to check me off her create-more-religious-people list.” Hashem wants each of us to reach out to our fellow Yidden to help them both materially and spiritually. If I do only what makes me feel comfortable and fulfilled, then I need to re-examine my motivation. Am I doing this to sooth my own conscience? When I’m ready to help another Jew on their terms, to get them what they need, that’s when I know I’m serving Hashem and not myself. Gedolah hatzedakah shemikareves es hageulah. May all our efforts in tzedakah—material and spiritual—hasten the coming of moshiach.  I heard this story from my uncle, Reb Efrayim Majesky a”h. It’s also printed in Ramasayim Tzofim to Tana D’vei Eliyahu, 27.
Good Shabbos, Rabbi Lipskier