Re'eh: Tzedakah: How Much?

(10) מסת נדבת ידך means sufficient (די) free-will offerings of thy hand (i.e. of thy possession): everything must be in accordance with the blessing (which God has bestowed upon you אשר יברכך): offer peace-offerings of rejoicing and invite guests for the meal.

(7) שעריך [WITHIN ANY OF] THY GATES — this implies that the poor of thine own city have preference over the poor of another city (Siphre; cf. Rashi on Exodus 22:24).

(7) לא תאמץ THOU SHALT NOT MAKE [THY HEART] OBSTINATE — There are people who painfully deliberate whether they should give or not, therefore Scripture states, “thou shalt not make thy heart obstinate”; there again are people who stretch their hand forth (show readiness to give) but then close it, therefore it is written, “thou shalt not close thine hand” (Siphre).

(8) פתח תפתח [BUT] THOU SHALT SURELY OPEN [THINE HAND] — even many times.

(8) והעבט תעביטנו AND THOU SHALT LEND HIM ON PLEDGE — If he does not want a gift, give it to him as a loan (cf. Siphre; Ketubot 67b).

(8) אשר יחסר לו [SUFFICIENT FOR HIS NEED] IN THAT WHICH HE LACKETH — This implies: you must provide him even with a horse to ride on and a slave to run before him (if he was accustomed to such and now feels the lack of them) (Siphre; Ketubot 67b).

(8) לו — implies that you must help him even to get a wife; for so it states. אעשה לו עזר כנגדו “I will make a helpmate for him (לו)” (Siphre; Ketubot 67b).

Do not harden your heart: to speak nice things to his heart

This is an infinitive. And any place where it is not written, it is short hand. But the midrash is also nice.

All who avert their eyes are called wicked, and it’s as if their worship is idol worship. And much so one is to be cautious about it, because it is possible that it will lead to bloodshed, that poor person who asks will die if there is none giving to his hand, like the story of Naham Ish Gamzu.