Commanded to Be Generous
(יב) כִּ֣י תְכַלֶּ֞ה לַ֠עְשֵׂר אֶת־כָּל־מַעְשַׂ֧ר תְּבוּאָתְךָ֛ בַּשָּׁנָ֥ה הַשְּׁלִישִׁ֖ת שְׁנַ֣ת הַֽמַּעֲשֵׂ֑ר וְנָתַתָּ֣ה לַלֵּוִ֗י לַגֵּר֙ לַיָּת֣וֹם וְלָֽאַלְמָנָ֔ה וְאָכְל֥וּ בִשְׁעָרֶ֖יךָ וְשָׂבֵֽעוּ׃ (יג) וְאָמַרְתָּ֡ לִפְנֵי֩ יְהוָ֨ה אֱלֹהֶ֜יךָ בִּעַ֧רְתִּי הַקֹּ֣דֶשׁ מִן־הַבַּ֗יִת וְגַ֨ם נְתַתִּ֤יו לַלֵּוִי֙ וְלַגֵּר֙ לַיָּת֣וֹם וְלָאַלְמָנָ֔ה כְּכָל־מִצְוָתְךָ֖ אֲשֶׁ֣ר צִוִּיתָ֑נִי לֹֽא־עָבַ֥רְתִּי מִמִּצְוֺתֶ֖יךָ וְלֹ֥א שָׁכָֽחְתִּי׃ (יד) לֹא־אָכַ֨לְתִּי בְאֹנִ֜י מִמֶּ֗נּוּ וְלֹא־בִעַ֤רְתִּי מִמֶּ֙נּוּ֙ בְּטָמֵ֔א וְלֹא־נָתַ֥תִּי מִמֶּ֖נּוּ לְמֵ֑ת שָׁמַ֗עְתִּי בְּקוֹל֙ יְהוָ֣ה אֱלֹהָ֔י עָשִׂ֕יתִי כְּכֹ֖ל אֲשֶׁ֥ר צִוִּיתָֽנִי׃ (טו) הַשְׁקִיפָה֩ מִמְּע֨וֹן קָדְשְׁךָ֜ מִן־הַשָּׁמַ֗יִם וּבָרֵ֤ךְ אֶֽת־עַמְּךָ֙ אֶת־יִשְׂרָאֵ֔ל וְאֵת֙ הָאֲדָמָ֔ה אֲשֶׁ֥ר נָתַ֖תָּה לָ֑נוּ כַּאֲשֶׁ֤ר נִשְׁבַּ֙עְתָּ֙ לַאֲבֹתֵ֔ינוּ אֶ֛רֶץ זָבַ֥ת חָלָ֖ב וּדְבָֽשׁ׃ (ס)

(12) When you have set aside in full the tenth part of your yield—in the third year, the year of the tithe—and have given it to the Levite, the stranger, the orphan, and the widow, that they may eat their fill in your settlements, (13) you shall declare before Adonai your God: “I have cleared out the consecrated portion from the house; and I have given it to the Levite, the stranger, the fatherless, and the widow, just as You commanded me; I have neither transgressed nor neglected any of Your commandments: (14) I have not eaten of it while in mourning, I have not cleared out any of it while I was unclean, and I have not deposited any of it with the dead. I have obeyed Adonai my God; I have done just as You commanded me. (15) Look down from Your holy abode, from heaven, and bless Your people Israel and the soil You have given us, a land flowing with milk and honey, as You swore to our fathers.”

(ג) ואכלו בשעריך ושבעו. תֵּן לָהֶם כְּדֵי שָׂבְעָן, מִכָּאן אָמְרוּ אֵין פּוֹחֲתִין לֶעָנִי בַּגֹּרֶן פָּחוֹת מֵחֲצִי קַב חִטִּים וְכוּ' (ספרי; תלמוד ירושלמי פאה פ"ח ה"ה):
(3) ואכלו בשעריך ושבעו THAT THEY MAY EAT WITHIN THY GATES, AND BE SATISFIED — Give them sufficient to satisfy them. From here they (the Rabbis) derived the law: one must give the poor in the barn no less than half a kab of wheat or a kab of barley (Sifrei Devarim 303:2; Talmud Yerushalmi Peah 8:5; see also Rashi on Deuteronomy 14:29).
(א) השקיפה ממעון קדשך. עָשִׂינוּ מַה שֶּׁגָּזַרְתָּ עָלֵינוּ, עֲשֵׂה אַתָּה מַה שֶּׁעָלֶיךָ לַעֲשׂוֹת (ספרי), שֶׁאָמַרְתָּ (ויקרא כ"ו) "אִם בְּחֻקֹּתַי תֵּלֵכוּ … וְנָתַתִּי גִשְׁמֵיכֶם בְּעִתָּם":
(1) השקיפה ממעון קדשך GLANCE DOWN FROM THE RESIDENCE OF THY HOLINESS . . [AND BLESS THY PEOPLE ISRAEL — “We have done what Thou hast laid upon us, do Thou now what has upon Thee to do, because Thou hast said, (Leviticus 25:3, 4) If ye walk in My ordinances … Then I will give you rain in its season etc.
(א) בערתי הקדש. שהוא המעשר. וגם שלא הפקדתיו רק נתתיו לאשר אני חייב לתת לו:
(1) I have removed that which is holy i.e., the tithe. Moreover, I have not stored it up; rather, I have given it to those to whom I am obliged to give it.
(ג) ולא שכחתי. שלא הוצאתי המעשר או פירושו על שני המעשרים:
(3) neither have I forgot to distribute the tithe. (It is also possible that these two verbs refer respectively to the two different tithes.)

We have done what you decreed for us: do that which You must do (Rashi). The word used by Rashi for "decree," gezeirah, generally implies a harsh command, and how does that fit into this context? If we examine it, though, we will realize that this is indeed a harsh decree. After all, how can a Jew be commanded to say: "I have done all that You commanded me"? Can any person make such a declaration without lying? Thus the decree is that we must make such a declaration regardless of the fact that it is not true.

R. Menahem Mendl of Kotzk

And have give it to the Levite, the stranger, the oprhan, and the widow, that they may eat within your gates, and be filled... The Torah added the word "and be filled" to teach us that when one gives tzedakah, they must be generous in how much they give.

Tiferet Shlomo

(ד) עַל הַסֵּדֶר הַזֶּה מַפְרִישִׁין בְּשָׁנָה רִאשׁוֹנָה מִן הַשָּׁבוּעַ וּבַשְּׁנִיָּה וּבָרְבִיעִית וּבַחֲמִישִׁית. אֲבָל בַּשְּׁלִישִׁית וּבַשִּׁשִּׁית מִן הַשָּׁבוּעַ אַחַר שֶׁמַּפְרִישִׁים מַעֲשֵׂר רִאשׁוֹן מַפְרִישׁ מִן הַשְּׁאָר מַעֲשֵׂר אַחֵר וְנוֹתְנוֹ לָעֲנִיִּים וְהוּא הַנִּקְרָא מַעֲשַׂר עָנִי. וְאֵין בִּשְׁתֵּי שָׁנִים אֵלּוּ מַעֲשֵׂר שֵׁנִי אֶלָּא מַעֲשַׂר עָנִי. וְעָלָיו נֶאֱמַר (דברים יד כח) "מִקְצֵה שָׁלֹשׁ שָׁנִים תּוֹצִיא אֶת כָּל מַעְשַׂר תְּבוּאָתְךָ בַּשָּׁנָה הַהִיא וְהִנַּחְתָּ בִּשְׁעָרֶיךָ" (דברים יד כט) "וּבָא הַלֵּוִי". וְעָלָיו נֶאֱמַר (דברים כו יב) "כִּי תְכַלֶּה לַעְשֵׂר":

(4) According to this system, they should tithe, in a seven year cycle, the first, second, fourth, and fifth years, but on the third and the sixth years of the seven year cycle, after one has tithed ma'asér rishon, one should take out from the remainder another tithe [one-tenth] and give it to the poor. This is called ma'esar ani. In these two years there is no ma'asér sheni but instead ma'esar ani.118See Babylonian Talmud Rosh Hashanah 12b. About this it is written, (Deut. 14:28-29) Every third year you shall bring out the full tithe of your yield of that year, but leave it within your settlements. Then the Levite, [who has no hereditary portion as you have, and the stranger, the fatherless, and the widow in your settlements shall come and eat their fill, so that the LORD your God may bless you in all the enterprises you undertake.] And about this it is written, (Deut. 26:12) When you have set aside in full the tenth part [of your yield in the third year--the year of the tithe--and have given it to the Levite, the stranger, the fatherless, and the widow, that they may eat their fill in your settlements].