If there will be among you a needy person, from one of your brothers in one of your cities... (15:7)
The poor of your city take precedence over the poor of a different city.
(Rashi)
Open, open your hand to him... (15:8)
Rabbi Elazar would give a coin to a pauper, and only then would he pray.
(Talmud, Bava Batra 10a)
Ten powerful things were created in the world: mountains are hard, but iron cuts through them; iron is hard, but fire melts it; fire is strong, but water extinguishes it; water is strong, but clouds bear it; clouds are strong, but wind scatters them; wind is strong, but the body contains it; the body is strong, bur fear breaks it; fear is potent, but wine dispels it; wine is powerful, but sleep assuages it; and stronger than all these is death. But charity delivers from death.
(Talmud, ibid.)
Turnusrufus asked Rabbi Akiva: "If your G‑d loves the poor, why doesn't He feed them?"
Said [Rabbi Akiva] to him: "So that we should be saved from purgatory (in the merit of the charity we give)."
Said he to him: "On the contrary: for this you deserve to be punished. I'll give you an analogy. This is analogous to a king who got angry at his slave and locked him away in a dungeon, and commanded that he not be given to eat or to drink; and a person came along and gave him to eat and to drink. When the king hears of this, is he not angry at that person...?"
Said Rabbi Akiva to him: "I'll give you an analogy. This is analogous to a king who got angry at his child and locked him away in a dungeon, and commanded that he not be given to eat or to drink; and a person came along and gave him to eat and to drink. When the king hears of this, does he not reward that person...?
(Talmud, ibid.)
King Munbaz squandered all his treasures, and the treasures put away by his ancestors, feeding the poor during years of hunger. His brothers and his father's family ganged up on him and said to him: "Your ancestors stored treasure and added to the treasures stored by their ancestors, and you squandered them!" Said he to them: "My ancestors stored below, and I stored above; my ancestors stored in a place where a foreign hand can reach, and I stored in a place where a foreign hand cannot reach; my ancestors stored things that do not bear fruit, and I stored things that bear fruit; my ancestors hoarded money, and I hoarded souls; my ancestors stored for others, and I stored for myself; my ancestors stored for this world, and I stored for the World to Come.
(Talmud, Bava Batra 11a)
Never, ever, have we seen or heard about a Jewish community that does not have a charity fund.
(Mishneh Torah, Laws of Gifts to the Poor 9:3)
There are eight levels of charity, each greater than the next.
[1] The greatest level, above which there is no greater, is to support a fellow Jew by endowing him with a gift or loan, or entering into a partnership with him, or finding employment for him, in order to strengthen his hand until he need no longer be dependent upon others...
[2] A lesser level of charity than this is to give to the poor without knowing to whom one gives, and without the recipient knowing from who he received. For this is performing a mitzvah solely for the sake of Heaven. This is like the "anonymous fund" that was in the Holy Temple [in Jerusalem]. There the righteous gave in secret, and the good poor profited in secret. Giving to a charity fund is similar to this mode of charity, though one should not contribute to a charity fund unless one knows that the person appointed over the fund is trustworthy and wise and a proper administrator, like Rabbi Hananya ben Teradyon.
[3] A lesser level of charity than this is when one knows to whom one gives, but the recipient does not know his benefactor. The greatest sages used to walk about in secret and put coins in the doors of the poor. It is worthy and truly good to do this if those who are responsible for distributing charity are not trustworthy.
[4] A lesser level of charity than this is when one does not know to whom one gives, but the poor person does know his benefactor. The greatest sages used to tie coins into their robes and throw them behind their backs, and the poor would come up and pick the coins out of their robes so that they would not be ashamed.
[5] A lesser level than this is when one gives to the poor person directly into his hand, but gives before being asked.
[6] A lesser level than this is when one gives to the poor person after being asked.
[7] A lesser level than this is when one gives inadequately, but gives gladly and with a smile.
[8] A lesser level than this is when one gives unwillingly.
(Mishneh Torah, Laws of Gifts to the Poor 10:7-14)