The Tzedakah Box Bandit (Parshas Terumah)
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In this week's parsha, we learn about the mitzvah of tzedakah. Rashi, commenting on the phrase in the first verse, "Take for Me terumah," explains that "for Me" means "for My sake – l'shem Shamayim." The Baal Shem Tov clarifies that this does not mean the donor must give tzedakah l'shem Shamayim, as the mitzvah is fulfilled as long as the recipient receives the funds. Rather, it teaches that the recipient must accept tzedakah l'shem Shamayim—meaning he may not take charity for needs beyond his or his organization’s essential expenses.
This highlights an important principle: anyone receiving charitable funds, whether an individual or an organization, must ensure that the funds are obtained in the most kosher manner.
With this in mind, let’s examine a real halachic dilemma that came before Rav Zilberstein (names changed).
Bart, the ever-dedicated friend of IJE, decided to launch a special tzedakah box project. He knew quite a few store owners along Gelt Gutter Avenue (where the sidewalks sparkle with credit card points), and he approached each one, asking if they’d be willing to place a tzedakah box at the register and encourage their customers to support this worthy cause.
The response was overwhelmingly positive—especially from Sidney Snatcher, the owner of Swipe & Splurge, a high-end gift shop with a steady stream of well-to-do customers eager to spend. As the months rolled by, the project was a smashing success, raising thousands of dollars. The box at Swipe & Splurge alone reliably collected around $1,500 each month, and Bart was thrilled.
That is, until one day, his Gemara Sleuth buddy, Rob, pulled him aside with a grave expression. Rob, an expert in gift display arrangements (a skill that earned him the nickname The Presentation Sensation), was occasionally called in by Sidney to rearrange the shop’s wares. One evening, as he was setting up a particularly fancy menorah display, he caught sight of Sidney engaged in an unusual activity—using a mini vacuum cleaner to suction a healthy stack of fives and tens out of the tzedakah box!
Sidney, blissfully unaware that he’d been spotted, carried on as if nothing had happened. But Rob had seen enough. And when, on a separate occasion, he witnessed the same shtick again, he knew he couldn’t stay silent. He told Bart everything.
Now Bart faced a serious moral and legal dilemma. Should he confront Sidney and call him out? If he did, Sidney might deny everything—or worse, remove the tzedakah box from the store altogether, cutting off the much-needed donations to IJE. Or maybe, Bart thought, he should change the box for one that had a padlock on it. But being that Sidney would see all the other tzedakah boxes in the others stores that do not have padlocks on them, he would be suspicious that his scam was discovered and stop allowing the box to remain in his store. And if Bart stayed silent, he’d be allowing Sidney to continue siphoning off tzedakah money like a back-alley ATM withdrawal.
What was the right thing to do? Bart and Rob launched into a fierce debate, armed with Gemaras, commentaries, and moral musings, analyzing every angle of this heist in halacha.
  1. CAN THEFT BE FORGIVEN?

(ג) מותר לב"ד לוותר בממון היתומים חוץ מן הדין כדי להשקיטם ממריבות:

(3) It is permissible for the Court of Law to forgo [certain] rights in property belonging to orphans [provided this is carried out by a settlement] out of Court in order to set them at peace from [entering into future] disputes.18Thus Isserlein. Derived from B.K. 21a: ‘A certain man built a mansion on the ruins belonging to orphans. R. Naḥman confiscated the mansion from him… originally Carmanians (MS.M קדמאי; MS.R. and Rashi קדמונאי ‘old settlers’ or ‘nomads’) had been living on the abandoned property belonging to the orphans and had been paying a nominal rent (Hence the orphans suffered a loss however small it was). (When R. Naḥman) said to him, Go and make a peaceful settlement with the orphans, he paid no attention. R. Naḥman, therefore, confiscated the mansion from him.’ This shows that although legally the defendant was responsible in full, nevertheless, R. Naḥman suggested at first a peaceful settlement. Likewise, the legal guardian of the orphans may make a settlement on behalf of the orphans which would ultimately be advantageous to their welfare. He should, however, make the settlement in accordance with a recognized Court of Law — P.Tesh.

2. IS INTENTION TO DO A SIN, ALSO A SIN?

דְּתַנְיָא: ״אִישָׁהּ הֲפֵרָם וַה׳ יִסְלַח לָהּ״, בַּמָּה הַכָּתוּב מְדַבֵּר? בְּאִשָּׁה שֶׁנָּדְרָה בְּנָזִיר, וְשָׁמַע בַּעְלָהּ וְהֵפֵר לָהּ, וְהִיא לֹא יָדְעָה שֶׁהֵפֵר לָהּ בַּעְלָהּ, וְהָיְתָה שׁוֹתָה יַיִן וּמִטַּמְּאָה לְמֵתִים. רַבִּי עֲקִיבָא כִּי הֲוָה מָטֵי לְהַאי פְּסוּקָא הֲוָה בָּכֵי, אָמַר: וּמָה מִי שֶׁנִּתְכַּוֵּין לֶאֱכוֹל בְּשַׂר חֲזִיר וְעָלָה בְּיָדוֹ בְּשַׂר טָלֶה, אָמְרָה תּוֹרָה: צְרִיכָה כַּפָּרָה וּסְלִיחָה, מִי שֶׁנִּתְכַּוֵּין לֶאֱכוֹל בְּשַׂר חֲזִיר וְעָלָה בְּיָדוֹ בְּשַׂר חֲזִיר – עַל אַחַת כַּמָּה וְכַמָּה.

The Gemara explains the source that one who intended to transgress is punished even though he did not actually sin. As it is taught in a baraita concerning a husband who nullified the vow of his wife: “Her husband has made them null; and the Lord will forgive her” (Numbers 30:13). With regard to what case is the verse speaking? Why would the woman require forgiveness if her husband has nullified her vow? It is referring to a woman who vowed to be a nazirite, and her husband heard and nullified her vow. And she did not know that her husband had nullified her vow, and she drank wine and contracted impurity from a corpse, violating her presumed vow. The Gemara relates: When Rabbi Akiva came to this verse he would cry. He said: And if with regard to one who intended to eat pork, and kosher lamb came up in his hand, like this woman who intended to violate her vow but in fact did not, the Torah nevertheless says: She requires atonement and forgiveness, all the more so does one who intended to eat pork and pork came up in his hand require atonement and forgiveness.

3. PUTTING A STUMBLING BLOCK BEFORE THE BLIND

(יד) לא תקלל חרש ולפני עור לא תתן מכשל ויראת מאלקיך אני יקוק

(14) You shall not insult the deaf, or place a stumbling block before the blind. You shall fear your God: I am יקוק.

(ב) ולפני עור לא תתן מכשול. לִפְנֵי הַסּוּמָא בְדָבָר לֹא תִתֵּן עֵצָה שֶׁאֵינָהּ הוֹגֶנֶת לוֹ, אַל תֹּאמַר מְכֹר שָׂדְךָ וְקַח לְךָ חֲמוֹר, וְאַתָּה עוֹקֵף עָלָיו וְנוֹטְלָהּ הֵימֶנּוּ (שם):

(2) ולפני עור לא תתן מכשל THOU SHALT NOT PUT A STUMBLING BLOCK BEFORE THE BLIND — This implies: "Give not a person who is "blind" in a matter an advice which is improper for him. Do not say to him: "Sell your field and buy from the proceeds of the sale an ass", the fact being that you are endeavouring to circumvent him and to take it (the field) from him (Sifra, Kedoshim, Section 2 14).

(ג) ויראת מאלקיך. לְפִי שֶׁהַדָּבָר הַזֶּה אֵינוֹ מָסוּר לַבְּרִיּוֹת לֵידַע אִם דַּעְתּוֹ שֶׁל זֶה לְטוֹבָה אוֹ לְרָעָה, וְיָכוֹל לְהִשָּׁמֵט וְלוֹמַר לְטוֹבָה נִתְכַּוַּנְתִּי, לְפִיכָךְ נֶאֱמַר בּוֹ וְיָרֵאתָ מֵּאֱלֹקֶיךָ הַמַּכִּיר מַחְשְׁבוֹתֶיךָ; וְכֵן כָּל דָּבָר הַמָּסוּר לְלִבּוֹ שֶׁל אָדָם הָעוֹשֵׂהוּ וְאֵין שְׁאָר הַבְּרִיּוֹת מַכִּירוֹת בּוֹ, נֶאֱמַר בּוֹ וְיָרֵאתָ מֵּאֱלֹקֶיךָ:

(3) ויראת מאלקיך BUT THOU SHALT BE AFRAID OF THY GOD — Because in this case it is not given to human beings to know whether the intention of this man (the offender) was for the advantage or the disadvantage of the person whom he advised, and he thus might be able to evade the responsibility by saying: "I meant it for the best", Scripture therefore states with reference to him: "But thou shall be afraid of thy God" Who is cognizant of thy secret thoughts. Similarly in all actions where it is given only to the heart of him who does it to know the motive that prompts him and where other people have no insight into it, Scripture states, "But be afraid of thy God!" (Sifra, Kedoshim, Section 2 14; Bava Metzia 58b).

מִנַּיִן שֶׁלֹּא יוֹשִׁיט אָדָם כּוֹס שֶׁל יַיִן לְנָזִיר, וְאֵבֶר מִן הַחַי לִבְנֵי נֹחַ? תַּלְמוּד לוֹמַר: ״וְלִפְנֵי עִוֵּר לֹא תִתֵּן מִכְשֹׁל״; וְהָא הָכָא, דְּכִי לָא יָהֲבִינַן לֵיהּ, שָׁקְלִי אִיהוּ, וְקָעָבַר מִשּׁוּם ״לִפְנֵי עִוֵּר לֹא תִתֵּן מִכְשֹׁל״! הָכָא בְּמַאי עָסְקִינַן? דְּקָאֵי בִּתְרֵי עֶבְרֵי נַהֲרָא. דַּיְקָא נָמֵי, דְּקָתָנֵי ״לֹא יוֹשִׁיט״ וְלָא קָתָנֵי ״לֹא יִתֵּן״, שְׁמַע מִינַּהּ.

From where is it derived that a person may not extend a cup of wine to a nazirite, who is prohibited from drinking wine, and that he may not extend a limb severed from a living animal to descendants of Noah? The verse states: “And you shall not put a stumbling block before the blind” (Leviticus 19:14). But here, in both cases, if one does not give it to him, he can take it himself, and yet the one who provides it to him transgresses due to the prohibition: “You shall not put a stumbling block before the blind.” The Gemara answers: Here we are dealing with a case where they are standing on the two sides of a river, and therefore the recipient could not have taken it himself. Since his help was instrumental, the one who conveyed the item has violated the prohibition of putting a stumbling block before the blind. The Gemara adds: The language of the baraita is also precise, as it teaches: A person may not extend, and it does not teach: One may not give. Learn from the usage of the term extend that the baraita is referring to one located on one side of a river, who extends the item to the one on the other side.

מנין שלא יושיט אדם כוס יין לנזיר - נראה דה"ה בכל שאר איסורין, אלא להכי נקט כוס יין לנזיר משום דמסתמא למישתי קא בעי ליה, כיון דכ"ע חמרא שתו, ושמא שכח נזירתו. אבל ישראל שאמר "הושיט לי נבלה או חזיר או שום איסור", אין לחושדו מלהושיט לו. אבל אם ידוע לו שרוצה לאכלו, אסור להושיט לו, ואפי' הוא שלו, מדקאמר "אי לא יהיב ליה שקיל ליה איהו". ולפי זה, אסור להושיט למומרים לעבודת כוכבים דבר איסור, אע"פ שהוא שלהם, כי הדבר ידוע שיאכלוהו, והוא נאסר להם דכישראל גמור חשבינן ליה. ומיירי בדקאי במקום שלא יוכל ליקח אם לא יושיט לו זה, וכדמסיק "דקאי בתרי עברי נהרא":

From where do we know that one should not hand a cup of wine to a Nazir?
It seems this principle applies to all prohibitions, but wine and a Nazir are mentioned because it's assumed the Nazir wants to drink it – everyone drinks wine, and he might have forgotten his Nazirite vow. However, if a Jew asked for neveilah (carrion), pork, or another clearly forbidden item, one wouldn't suspect he intends to eat it and therefore wouldn't hesitate to hand it over. But if it's known he does intend to consume it, handing it over is forbidden, even if it's his own property. This is implied by the question, "if you don't give it, he'll take it himself!" Therefore, it's also forbidden to give apostates something forbidden to them, even if it's theirs, because they'll certainly consume it, and they're still considered fully Jewish. This applies when the sinner is in a situation where they can only obtain the forbidden object if someone else hands it to them, as the Gemara concludes, like being on opposite banks of a river.

4. PEOPLE WHO WANT TO STUMBLE

הגה...אע"פ שחייב אדם למחות בעוברי עבירה וכל מי שאינו מוחה ובידו למחות נתפס באותו עון מ"מ אין אדם חייב להוציא ממונו על זה ולכן נהגו להקל מלמחות בעוברי עבירה שיש לחוש שיהיו עומדין על גופינו ומאודנו (מהרי"ו סי' קנ"ז) :

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Similarly, R’ Shlomo Zalman Auerbach zt”l (Teshuvos Minchas Shlomo 1:7) discusses the case of a borrower who refuses to return the loan and threatens that if the lender sues him in court, he will curse Hashem’s Name. Even if the lender knows that the borrower will make good on his threat, he may still sue him. This is not considered placing a stumbling block before the blind. It is no worse than any normal case of a borrower who denies owing money. The lender may demand an oath from him in Beis Din, even if he knows that the borrower will lie under oath. False oaths are so severe that the entire world can be punished for it. Nevertheless, this is the lying borrower’s problem, not the honest lender’s. The lender may demand an oath for the money he is owed, and need not concern himself with the sinful false oath that the borrower will make as a consequence.