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Can I Make a Berakha on non-Kosher Food?
1. Bava Kamma 95a

דְּתַנְיָא: רַבִּי אֱלִיעֶזֶר בֶּן יַעֲקֹב אוֹמֵר: הֲרֵי שֶׁגָּזַל סְאָה שֶׁל חִטִּין, טְחָנָהּ, לָשָׁה, וַאֲפָאָהּ וְהִפְרִישׁ מִמֶּנָּה חַלָּה, כֵּיצַד מְבָרֵךְ? אֵין זֶה מְבָרֵךְ אֶלָּא מְנָאֵץ! וְעַל זֶה נֶאֱמַר ''(תְּהִלִּים י':ג') בֹּצֵעַ בֵּרֵךְ נִאֵץ ה'.''

Rabbi Eliezer ben Ya’akov says: In the case of one who robbed another of a se’a of wheat, then ground it, kneaded it, and baked it, and he then separated challa from it, [i.e., he separated the portion of the dough that one is required to separate and then give to a priest,] how can he recite the blessing over the separation of challa? This individual is not reciting a blessing, but rather he is insulting/disrespecting God. And with regard to this it is stated: “The robber who recites a blessing disrespects Hashem (Psalms 10:3).”

2. Berakhot 45a

שְׁלֹשָׁה שֶׁאָכְלוּ כְּאַחַת, חַיָּיבִין לְזַמֵּן...אָכַל טֶבֶל, וּמַעֲשֵׂר רִאשׁוֹן שֶׁלֹּא נִטְּלָה תְּרוּמָתוֹ… אֵין מְזַמְּנִין עָלָיו.

Three who ate together as one are obligated to perform a zimmun [before bentching]... One who ate untithed produce [tevel], and first tithe from which its teruma was not separated… is not included among the three obligated with whom they ate in a zimmun.

3. Rambam, Laws of Berakhot 1:19

כָּל הָאוֹכֵל דָּבָר הָאָסוּר, בֵּין בְּזָדוֹן בֵּין בִּשְׁגָגָה - אֵינוֹ מְבָרֵךְ עָלָיו לֹא בַּתְּחִלָּה וְלֹא בַּסּוֹף. כֵּיצַד? הֲרֵי שֶׁאָכַל טֶבֶל, וַאֲפִלּוּ טֶבֶל דְּדִבְרֵיהֶם, אוֹ שֶׁאָכַל מַעֲשֵׂר רִאשׁוֹן שֶׁלֹּא נִטְּלוּ כָּל תְּרוּמוֹתָיו אוֹ מַעֲשֵׂר שֵׁנִי וְהֶקְדֵּשׁ שֶׁלֹּא נִפְדּוּ כְּהִלְכָתָן - אֵינוֹ מְבָרֵךְ. וְאֵין צָרִיךְ לוֹמַר אִם אָכַל נְבֵלוֹת וּטְרֵפוֹת אוֹ שָׁתָה יֵין נֶסֶךְ וְכַיּוֹצֵא בָּהֶן.

Whoever eats forbidden food, wilfully or in error—recites no blessing either before or after. For example, if one eats of that which is Rabbinically regarded as Tevel (produce from which priest's dues and Levite's tithes should have been, but had not been separated), or eats Levite's tithes from which the priest's dues (two per cent by the original owners, and ten per cent by the Levite of his portion) had not been taken, or eats (outside Jerusalem) Second tithes (which should be consumed in Jerusalem), or consumes that which had been set apart for the Sanctuary and had not been properly redeemed, he does not recite the blessings for the food. Needless to add that no blessing is recited if flesh is eaten of a beast that was not properly slain or was pronounced unfit for consumption by Jews owing to a lesion, or if wine is drunk that is forbidden to Jews etc.

4. Ra’avad ad loc. (Rabbi Abraham ben David, 12th Century France)

אָמַר אַבְרָהָם: טָעָה בְּזֶה טָעוּת גְּדוֹלָה שֶׁלֹּא אָמְרוּ שֶׁאֵין מְבָרְכִין אֶלָּא שֶׁאֵין מְזַמְּנִין עֲלֵיהֶם לוֹמַר שֶׁאֵין לָהֶם חֲשִׁיבוּת קְבִיעוּת הוֹאִיל וְאוֹכְלִין דָּבָר הָאָסוּר וְהוּא כְּעֵין אֲכִילַת פֵּרוֹת שֶׁאֵין לָהֶם קֶבַע לְזִמּוּן, אֲבָל בְּרָכָה תְּחִלָּה וְסוֹף לָמָּה לֹא יְבָרְכוּ הוֹאִיל וְנֶהֱנוּ?!

[The Rambam] made a big mistake [in understanding the mishna]. The mishna doesn’t say to not recite berachot, but it says that one does not do a zimmun for birkat ha-mazon because eating forbidden foods has no value in contributing to a zimmun, it’s like eating fruits [which is not satisfying enough to say birkat ha-mazon/zimmun after eating]. But why should you not make a beracha before and after eating [something forbidden], didn’t you benefit from eating it?!

5. Berakhot 35a

תָּנוּ רַבָּנַן: אָסוּר לוֹ לָאָדָם שֶׁיֵּהָנֶה מִן הָעוֹלָם הַזֶּה בְּלֹא בְּרָכָה. וְכׇל הַנֶּהֱנֶה מִן הָעוֹלָם הַזֶּה בְּלֹא בְּרָכָה מָעַל.

The Sages taught in a Tosefta: One is forbidden to derive benefit from this world, which is the property of God, without reciting a blessing beforehand. And anyone who derives benefit from this world without a blessing, it is as if he is guilty of misuse of a consecrated object.

6. Shulchan Aruch 196:1-2 (Rabbi Yosef Karo, 15th Century Spain/Israel)

אָכַל דְּבַר אִסוּר, אַף עַל פִּי שֶׁאֵינוֹ אָסוּר אֶלָּא מִדְּרַבָּנָן, אֵין מְזַמְּנִין עָלָיו וְאֵין מְבָרְכִין עָלָיו לֹא בִּתְחִלָּה וְלֹא בַּסוֹף. אִם אָכַל דְּבַר אִסוּר בִּמְקוֹם סַכָּנָה, מְבָרְכִים עָלָיו.

If you ate something forbidden, even if it’s only rabbinically prohibited, you don’t participate in a zimmun and you don’t make a beracha on it before or after eating. If you ate something forbidden because your life was in danger, you should make a beracha before and after eating it.

7. Peninei Halakha Berakhot 12:10 (Rabbi Eliezer Melamed, Modern-day Israel)

(ד) הָאוֹכֵל מַאֲכָל כָּשֵׁר בְּשָׁעָה שֶׁאָסוּר לוֹ לֶאֱכֹל, כְּגוֹן שֶׁאוֹכֵל בְּתַעֲנִית, אוֹ בְּמוֹצָאֵי שַׁבָּת לִפְנֵי הַבְדָּלָה, אוֹ לִפְנֵי תְּפִלַּת שַׁחֲרִית, אוֹ בְּסוֹכוֹת מִחוּץ לַסֻּכָּה, כֵּיוָן שֶׁהַמַּאֲכָל עַצְמוֹ כָּשֵׁר וְרַק זְמַן הָאֲכִילָה אוֹ מְקוֹמָהּ אֵינָם רְאוּיִים, צָרִיךְ לְבָרֵךְ עַל הֲנָאָתוֹ מֵהַמַּאֲכָל הַכָּשֵׁר.

Someone who eats kosher food but at time where it is forbidden to eat (for example, on a fast day, or on Saturday night before saying havdala, or before Shacharit, or outside of a sukka on Sukkot, since the food itself is kosher but it’s not the right time/place to be eating it, you must make a beracha on the benefit/enjoyment of eating the kosher food.

This source sheet accompanied an after-school learning program at SAR High School. Check out my Twitter thread on how to facilitate this session and how my students responded: https://twitter.com/tzvei_dinim/status/1481049620616728582?s=21