"Bind up the money in your hand" (Deuteronomy, 14:25)
Bind up your money and keep it in your hand—in your control. You should con-trol your wealth—not let your wealth bind and control you.
(Rabbi Meir of Premishlan)
"You shall open your hand to him" (Deuteronomy 15:8)
From this verse our Sages learned that charity is a positive commandment from the Torah. If so, why do we not recite a blessing before fulfilling this mitzvah?
Because if pious people would pause to make all the customary preparations be-fore the blessing—washing their hands, reciting L'shem Yichud, and so on—the poor person might die of hunger while they were preparing.
(Rabbi Bunim of Peshischa)
"You shall surely give to him, and your heart shall not be grieved when you give to him..." (Deuteronomy 15:10)
Even if a person gives generously to the poor, if he lacks genuine empathy for the poor person's situation, it is considered akin to bloodshed.
(the Baal Shem Tov)
"...and you will begrudge your needy brother and not give him, and he will cry out to the L-rd against you, and it will be a sin to you." (Deuteronomy 15:9)
If not only do you fail to help the poor man, but you also look upon him with a begrudging eye and attribute his suffering and distress to his own sins, then "he will cry out to the L-rd against you." Heaven will examine your deeds, and "it will be a sin to you"—your own sins will be re-membered.
(Rabbi Shmelke of Nikolsburg)