Midras Amsal 18:16: Devarim Rabbah, Midrash Tanchuma, Vayikra Rabbah & Bamidbar Rabbah

מַתָּ֣ן אָ֭דָם יַרְחִ֣יב ל֑וֹ וְלִפְנֵ֖י גְדֹלִ֣ים יַנְחֶֽנּוּ׃

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Devarim Rabbah

“When the Lord your God will expand your border” – this is what the verse said: “A man’s giving expands for him, and will guide him before the great” (Proverbs 18:16). What is [the meaning of] “a man’s giving expands for him”? There was an incident involving Rabbi Eliezer and Rabbi Yehoshua who went out to collect for the matter of a mitzva for our rabbis.12They sought to collect donations to support the rabbis. They went to the environs of Antioch and there was a certain man there who was called Abba Yudan, who was accustomed to giving generously to our rabbis. That Abba Yudan had become poor. He saw that Rabbi Eliezer and Rabbi Yehoshua had come there to collect, and he concealed himself from them and entered his house. He spent a day there, and a second, and did not go down to the marketplace. His wife said to him: ‘Why did you not go down to the marketplace these two days?’ He said to her: ‘Our rabbis came to collect for the matter of a mitzva for those who toil in Torah. I do not have enough to give them and I am embarrassed to go down to the marketplace.’ His wife, who was very fond of mitzvot, said to him: ‘Do we not have one field remaining? Sell half of it and give [the money] to them.’ He went and he did so. He sold half of the field for five gold pieces and gave them to our rabbis. He said to them: ‘Pray on my behalf.’ They prayed on his behalf and said to him: ‘May the Omnipresent restore what you have lost.’ Our rabbis went on their way to collect elsewhere. That Abba Yudan plowed half the field and found a large hidden treasure. He became wealthier than he had been previously. When our rabbis were returning, they passed through that same place. They said to someone: ‘As you live, arrange a meeting for us with Abba Yudan.’ That man said to them: ‘Who can arrange a meeting – with the king and not with him.’13It is easier to meet the king than to meet with Abba Yudan. They said to him: ‘We seek only to ensure that he will not find out that we passed here and did not inquire after his wellbeing.’ Abba Yudan found out and came to them and gave them one thousand gold pieces. He said to them: ‘Your prayer bore fruit.’ They said to him: ‘We were aware of your good deeds and placed you at the head of the list.’ The Sages read in his regard: “A man’s giving expands for him, and will guide him before the great.”
Another matter, there was an incident involving Rabbi Ḥiyya, who held a fundraising campaign in the great study hall in Tiberias and a certain person pledged a litra of gold.14This was a very significant sum of money. Rabbi Ḥiyya took him, seated him next to him, and read in his regard: “A man’s giving expands for him [and will guide him before the great].”15Rabbi Ḥiyya was indicating that, just as the end of the verse had been fulfilled, as he had been seated among prominent people, he should fulfill the beginning of the verse, by making good on his pledge and giving generously (Etz Yosef).
Another matter, there was an incident involving Reish Lakish who went to Basra. There was a certain person there who was called Avin Ramaa. It is not that he was, God forbid, a swindler [ramai], but rather, he would employ cunning [merameh] regarding mitzvot. The entire congregation would pledge, and then he would pledge a sum corresponding to that of the entire congregation.16At first he would abstain from making any pledge, leading others to think he would not participate. Therefore they would pledge more money, so that the charity collection would meet its goals. Only afterward would he pledge as much as everyone else donated together. Alternatively, the people would know that he would match their donations and therefore they would pledge more, knowing that their donation would lead to even greater gain for the charity. Reish Lakish held a fundraising campaign there and he gave corresponding to the entire congregation. Reish Lakish took him, seated him next to him, and read in his regard: “A man’s giving expands for him, and will guide him before the great.” Rabbi Abahu said: Why do I need another place, derive it from its own place.17Why do I need to derive from a verse in Psalms that if someone gives charity generously he will be rewarded materially, when this can be derived from the Torah itself? What is written prior to it? “Beware lest you forsake the Levite” (Deuteronomy 12:19) and then, “when the Lord your God will expand your border, as He spoke to you.”18The juxtaposition of the verses indicates that if the Israelites take care of the Levites, who did not have ancestral property, God will expand their borders.
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Midrash Tanchuma

When the Lord enlarges your territory (Deuteronomy 12:20): This is what is stated in the verse (Proverbs 18:16), "A man’s gift eases his way." It is a gift so that a person will give from his, that the Holy One, blessed be He, enlarges [what he has]. There is a [relevant] story about Abbun Ramah (probably a nickname, meaning the father of tricking) who lived in Batsra. His rabbis went to there and were seeking sustenance. He sat and did not decide [what he would give] at first, until all the people of the city decided, so that he could decide corresponding to all [the others]. That is why he was called Abbun Ramah, as he would be tricky with all of the commandments. From when he knew how much all of the people of the city had decided, he decided corresponding to all of them. What did our rabbis do? They took him and sat him at the edge next to them, in order to fulfill that which is stated, "A man’s gift eases his way [and places him next to the great]." Another interpretation of "A man’s gift eases his way": This is [referring to] Avraham. When he chased the [four] kings, the king of Sodom came out to greet him. He said to him (Genesis 14:21), "Give me the persons, and take the possessions for yourself." Avraham said [back], "I have raised my hand to the Lord, God Most High [.... I will not take] so much as a thread or a sandal strap, etc." The Holy One, blessed be He, said to him, "You have said, 'a thread [or a sandal strap]." By your life, I will sustain your children with that same expression, 'How lovely are your feet in sandals' (Song of Songs 7:2)." Another interpretation of "A man’s gift eases his way": This is [referring to] Israel. When the Holy One, blessed be He, said to them to bring a freewill offering, what is written there? "These continued to bring freewill offerings to [Moshe] morning after morning" (Exodus 36:3), two mornings. What did they merit [by this]? He enlarged their territory, as stated, "When the Lord enlarges your territory." In the merit of what does He enlarge it, "as he stated to you" (Deuteronomy 12:20)? In the merit of the ten statements (Ten Commandments) that you accepted. Another interpretation: "As he stated," in the merit of your forefathers.
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Vayikra Rabbah

“A man’s giving expands him [and guides him among the great]” (Proverbs 18:16). There was an incident involving Rabbi Eliezer, Rabbi Yehoshua, and Rabbi Akiva, who went to the environs of Antioch to engage in collecting charity for the Sages. There was a certain person there whose name was Abba Yudan, and he would generously provide support. One time, he had become impoverished, and when he saw our rabbis there he turned pale. He went to his wife. His wife said to him: ‘Why is your face sickly?’ He said to her: ‘My rabbis are here and I do not know what to do.’ His wife, who was more righteous than he, said to him: ‘All that remains for us is such and such field. Go and sell half of it and give it to them.’ He sold half of it and gave it to them. They prayed on his behalf and said: ‘May the Holy One blessed be He restore what you have lost.’ Sometime later, he went to plow his half field. As he was plowing, the earth opened before him and his cow fell there and its leg was broken. He descended to take it up, and the Holy One blessed be He illuminated his eyes and he found buried treasure there. He said: ‘My cow’s leg was broken for my benefit.’ When the rabbis returned there, they asked about him and said: ‘How is Abba Yudan doing?’ They said to him: ‘He is Abba Yudan with the slaves, Abba Yudan with the goats, Abba Yudan with the camels, Abba Yudan with the oxen. Who is able to see the face of Abba Yudan?’ When he heard [that they had come], he went out to greet them. They said to him: ‘How is Abba Yudan doing?’ He said: ‘Your prayer bore fruit and the fruit bore fruit.’ They said to him: ‘As you live, even though others gave more than you, we wrote you at the head [of the list].’ They took him and seated him in their midst, and they read this verse in his regard: “A man’s giving expands him.”
Rabbi Shimon ben Lakish went to Basra. There was a certain person there whose name was Abba Yudan Ramai. Not that, Heaven forbid, he was a swindler [ramai], but rather because he would employ cunning [meramei] in mitzvot. When all the people would pledge donations, he would pledge corresponding to them all.12At first he would abstain from making any pledge, leading others to think he would not participate. Therefore they would pledge more money so that the charity collection would meet its goals. Only afterward would he pledge as much as everyone else put together. Alternatively, the people would know that he would match their donations and therefore they would pledge more, knowing that their donation would lead to even greater gain for the charity. Rabbi Shimon ben Lakish took him and seated him next to him and read this verse in his regard: “A man’s giving expands him.”
Rabbi Ḥiyya bar Abba conducted a fundraising campaign to donate to the study hall in Tiberias. There was a certain person there, a resident of Silkha, who pledged one liter of gold. Rabbi Ḥiyya took him and seated him next to him and read this verse in his regard: “A man’s giving expands him.” Rabbi Abahu said: It is written: “Beware, lest you forsake the Levite” (Deuteronomy 12:19), and it is written thereafter: “When the Lord your God will expand your border” (Deuteronomy 12:20). What does one matter have to do with the other? It is that the Holy One blessed be He said: In accordance with your gifts, [God] will expand your [wealth].
Rabbi Aḥa in the name of Rabbi Hoshaya: If a servant brings a bull and his master brings a bull, the servant precedes his master, as it is taught there: If the bull of the anointed priest and the bull of the congregation are pending, the bull of the anointed priest precedes the bull of the congregation in all actions done to it.13Mishna Horayot 3:6.
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