Chessed
(כב) כִּי֩ אִם־שָׁמֹ֨ר תִּשְׁמְר֜וּן אֶת־כָּל־הַמִּצְוָ֣ה הַזֹּ֗את אֲשֶׁ֧ר אָנֹכִ֛י מְצַוֶּ֥ה אֶתְכֶ֖ם לַעֲשֹׂתָ֑הּ לְאַהֲבָ֞ה אֶת־יקוק אֱלֹקֵיכֶ֛ם לָלֶ֥כֶת בְּכָל־דְּרָכָ֖יו וּלְדָבְקָה־בֽוֹ׃
(22) If, then, you faithfully keep all this Instruction that I command you, loving the LORD your God, walking in all His ways, and holding fast to Him,

(א) ללכת בכל דרכיו - אלו דרכי הקב"ה, שנ' (שמות לד) יקוק יקוק אל רחום וחנון, ארץ אפים ורב חסד ואמת, נוצר חסד לאלפים, נושא עון ופשע וחטאה ונקה. ואו' (יואל ג) כל אשר יקרא בשם יקוק ימלט. וכי היאך אפשר לו לאדם להיקרא בשמו של הקב"ה? אלא מה המקום נקרא רחום וחנון - אף אתה הוי רחום וחנון ועשה מתנת חנם לכל. מה הקב"ה נקרא צדיק, שנ' (תהלים קמה) צדיק יקוק בכל דרכיו וחסיד בכל מעשיו - אף אתה הוי צדיק. הקב"ה נקרא חסיד, שנאמ' וחסיד בכל מעשיו - אף אתה הוי חסיד; לכך נאמר כל אשר יקרא בשם יקוק ימלט, ואומר (ישעיה מג) כל הנקרא בשמי ולכבודי בראתיו, יצרתיו אף עשיתיו, ואו' (משלי טז) כל פעל יקוק למענהו:

(ב) ולדבקה בו. וכי היאך אפשר לו לאדם לעלות במרום ולהדבק בו? והלא כבר נאמר (דברים ד׳:כ״ד) כי יקוק אלקיך אש אוכלה הוא! ואומר (דניאל ז׳:ט׳) כורסיה שביבים דנור יגלגלוהי נור דליק! אלא הדבק בחכמים ובתלמידים, ומעלה אני עליך כאלו עלית למרום ונטלתם. ולא שעלית ונטלת בשלום, אלא אפילו כאלו עשית מלחמה ונטלת! וכן הוא אומר (תהלים סח) עלית למרום שבית שבי לקחת מתנות באדם.

(ג) דורשי רשומות אומרים: רצונך שתכיר מי שאמר והיה העולם? - למוד הגדה, שמתוך כך אתה מכיר את הקב"ה ומדבק בדרכיו. ואם עשיתם מה שעליכם - אף אני אעשה מה שעלי:

(1) (Devarim 11:22) "to walk in His ways": Which are the ways of the Holy One Blessed be He? (Shemoth 34:6-7) "The L-rd, the L-rd, G-d of mercy and grace, slow to wrath and abundant in mercy and truth, keeping lovingkindness for thousands, forgiving transgression, offense, and sin, and cleansing …" And it is written (Yoel 3:5) "All who will be called by the name of the L-rd will escape": Now how is it possible for a man to be called by the name of the Holy One Blessed be He? But, (the intent is) just as the L-rd is called "merciful and gracious," you, too, be merciful and gracious, and give gratuitously to all. Just as the Holy One Blessed be He is called "righteous," viz. (Psalms 145:17) "Righteous is the L-rd in all His ways and saintly in all His acts" — you, too, be righteous. Just as the Holy One Blessed be He is called "saintly," — you, too, be saintly. This is the intent of "All who will be called by the name of the L-rd will escape." And it is written (Isaiah 43:7) "… everyone that is called by My name. For My honor I have created him, and formed him, and fashioned him." And it is written (Proverbs 16:4) "The L-rd has created all for His sake." (Devarim, Ibid.)

(2) "and to cleave to Him": How is it possible for a man to ascend the heights and cleave to Him? Is it not written (Ibid. 4:24) "For the L-rd your G-d is a consuming fire"? and (Daniel 8:9) "His throne was like a fiery flame and its wheels like burning fire"? But, (the intent is) cleave to the sages and to the disciples, and I will account it to you as if you had ascended the heights and had taken it (the Torah). And not as if you had taken it peacefully, but as if you had waged war and taken it. And thus is it written (Psalms 68:19) "You ascended on high; you took spoils; you took gifts for man."

(3) The expounders of metaphor say: Do you wish to recognize the One who spoke and brought the world into being? Learn haggadah. For if you do so, you will come to recognize the Holy One Blessed be He and cleave to His ways. And if you do yours, then I will do Mine, (Devarim 11:23) "and the L-rd will drive out, etc."

(ו) כָּךְ לָמְדוּ בְּפֵרוּשׁ מִצְוָה זוֹ. מַה הוּא נִקְרָא חַנּוּן אַף אַתָּה הֱיֵה חַנּוּן. מַה הוּא נִקְרָא רַחוּם אַף אַתָּה הֱיֵה רַחוּם. מַה הוּא נִקְרָא קָדוֹשׁ אַף אַתָּה הֱיֵה קָדוֹשׁ. וְעַל דֶּרֶךְ זוֹ קָרְאוּ הַנְּבִיאִים לָאֵל בְּכָל אוֹתָן הַכִּנּוּיִין אֶרֶךְ אַפַּיִם וְרַב חֶסֶד צַדִּיק וְיָשָׁר תָּמִים גִּבּוֹר וְחָזָק וְכַיּוֹצֵא בָּהֶן. לְהוֹדִיעַ שֶׁהֵן דְּרָכִים טוֹבִים וִישָׁרִים וְחַיָּב אָדָם לְהַנְהִיג עַצְמוֹ בָּהֶן וּלְהִדַּמּוֹת אֵלָיו כְּפִי כֹּחוֹ:

(6) In explaining this commandment the sages taught thus: Even as He is called gracious, be thou gracious; even as He is called merciful, be thou merciful; even as He is called holy, be thou holy.4Shabbat, 133b.; Sotah, 14a. C. In this way did the prophets attribute to God all such terms as long-suffering, abundant in benificence, just and right, perfect, mighty and powerful and others like these, to proclaim that they are good and straight paths, and that man is obligated to lead himself in them, and to be like unto Him in proportion to his power.

דרש ר' שמלאי תורה תחלתה גמילות חסדים וסופה גמילות חסדים תחילתה גמילות חסדים דכתיב ויעש יקוק אלקים לאדם ולאשתו כתנות עור וילבישם וסופה גמילות חסדים דכתיב ויקבר אותו בגיא
Rabbi Samlai taught: With regard to the Torah, its beginning is an act of kindness and its end is an act of kindness. Its beginning is an act of kindness, as it is written: “And the Lord God made for Adam and for his wife garments of skin, and clothed them” (Genesis 3:21). And its end is an act of kindness, as it is written: “And he was buried in the valley in the land of Moab” (Deuteronomy 34:6).
ת"ר בשלשה דברים גדולה גמילות חסדים יותר מן הצדקה צדקה בממונו גמילות חסדים בין בגופו בין בממונו צדקה לעניים גמילות חסדים בין לעניים בין לעשירים צדקה לחיים גמילות חסדים בין לחיים בין למתים
The Sages taught that acts of kindness are superior to charity in three respects: Charity can be performed only with one’s money, while acts of kindness can be performed both with his person and with his money. Charity is given to the poor, while acts of kindness are performed both for the poor and for the rich. Charity is given to the living, while acts of kindness are performed both for the living and for the dead.

Rabbi Jonathan Sacks - The Way of Chessed: Love as Compassion

Tzedakah is the gift of money or its equivalent. But sometimes that is not what we most need. We can suffer emotional as well as physical poverty. We can be depressed, lonely, close to despair. We may need company or comfort, encouragement or support. These too are human needs, no less real for being untranslatable into the language of politics or economics.

That is what chessed is about: emotional support, ‘loving-kindness’, love as compassion. It is what we mean when we speak of God in Psalm 147 as one who ‘heals the broken-hearted and binds up their wounds’. It includes hospitality to the lonely, visiting the sick, comforting the bereaved, raising the spirits of the depressed, helping people through crises in their lives, and making those at the margins feel part of the community.

It is tzedakah’s other side. Tzedakah is done with material goods, chessed with psychological ones: time and care. Tzedakah is practical support, chessed is emotional support. Tzedakah is a gift of resources, chessed a gift of the person. Even those who lack the means to give tzedakah can still give chessed. Tzedakah rights wrongs; chessed humanizes fate.

Abraham and Sarah were chosen because of their chessed to others. Ruth became the ancestress of Israel’s kings because of her chessed to Naomi. At the heart of the Judaic vision is the dream of a society based on chessed: society with a human face, not one dominated by the competition for wealth or power. Chessed is the mark of a people joined by covenant. Covenant creates society-as-extended-family; it means seeing strangers as if they were our long-lost brothers or sisters. A community based on chessed is a place of grace, where everyone feels honoured and everyone is at home.

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