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According to those Shitos (such as the Ran) brought in Is a neder about something compulsory valid? that one violates Lo Yachel Devaro if they break a Neder not to do something which is already Assur, what would be the Halacha in the following case:

Reuven makes a Neder not to eat pork. However, a month later he realizes that he cannot stop himself from eating pork, no matter how hard he tries. He then goes to a Beis Din to ask them to be "Matir Neder". Assuming they find Halachic grounds to be Matir this Neder:

  1. Is it appropriate for the Beis Din to be Matir Neder in order to save Reuven from the extra Aveira each time he eats pork?
  2. Should the possibility (or, according to some, the inevitability) that their Heter will be considered by some as sanctioning the eating of pork be a reason to avoid being Matir it?
  • Is this actually a neder, or is it considered a shevuah (negative about the future)? If it is a shevuah, it may be a shevuas shav (it’s pointless). It’s been a while since I did the sugya, so I may be way off; someone who does daf yomi would be better equipped to answer this. – DonielF Dec 21 '17 at 4:02
  • @DonielF I don't know the exact rules, but see here (judaism.stackexchange.com/questions/14884/neder-vs-shevua) which lays out a simple definition, so it could easily be said in a way that it would be a neder or shevuah. – רבות מחשבות Dec 21 '17 at 4:07
  • @DonielF Also, note that I am basing my question on the conclusion of "Is a neder about something compulsory valid?", which is quoted above, so we are assuming it is a valid neder/shevuah for this question. – רבות מחשבות Dec 21 '17 at 4:08
  • This seems related to the question of the propriety of increasing the chances of smaller sins to prevent larger sins, and the question of whether it is ever appropriate for society, or its formal representative; the courts, to sanction, or appear to sanction, anything prohibited. A famous application is a woman in a single woman in an illicit sexual relationship going to the mikve, and whether it should be allowed / encouraged, see Rivash (425) who would not encourage it. – mevaqesh Dec 21 '17 at 4:35
  • See also Akedat Yitshak (Vayera 20) who states that the courts mustn't support prostitutes under the argument that they prevent men from worse sin, and Rivash similarly condemned this. Similarly, see Maharsham (551:30) regarding sale of meat during the week of 9 bav lest people buy non-kosher meat. He too condemns this. – mevaqesh Dec 21 '17 at 4:35
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A similar question is the subject of much discussion in YD 228. Rav Moshe Stern, the Debreciner Rav, in Shu"t Beer Moshe Chelek Gimel, Siman 163-165 (which includes the summary of his answer), was asked about a person who promised never to bring a TV into his house, and now wanted him to be Matir his Neder:

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Basically his answer is that it is Assur to be Matir such a Neder, and it is based off of his understanding of the Poskim in the Sugya (it's important to see Tur/SA/Rema 128:16 and Nosei Keilim on all of that). His main decisions are based on the Shu"t Rivash 43:2 (copied below), although there is some room for Heter in certain cases based off the Shu"t Rema 103. All of the discussion revolves around being Matir a Neder not to do a prohibited act, with the classic example being Mesachek Bekubiya, or gambling.

... אבל שבועה שנעשית למנוע מאסור אין מתירין אותה. ושחוק בקוביא, הנה יש בו אסורא דרבנן, כדאיתא בסנהדרין פרק זה בורר (כ"ד:). ואפילו לרב ששת דס"ל התם דליכא אסמכתא בקוביא, מ"מ דבר מכוער ומתועב ומשוקץ הוא. ורבים חללים הפיל ועצומים כל הרוגיו. ומפורש הוא בירושלמי (נדרים פ"ה ה"ד) דמי שנדר שלא לצחוק, אין מתירין אותו. וכן דעת הרמב"ן ז"ל במשפט החרם שלו וכ"כ הרשב"א ז"ל בתשובה...

After the fact, he brought the Orchos Chaim (Hilchos Shevuos Unedarim), who says that according to Ramban and Semak it is Assur to be Matir a promise not to gamble, and even if he is already gambling, we should fine him and place him in "Nidui":

...מי שנשבע שלא לשחק בקוביא, אפילו עבר כבר על שבועתו אסור להתיר לו כדי שלא יהיה חוטא נשכר, אלא יש לנדותו ולהבדילו עד שישים קנס עליו ויקבל על עצמו שלא ישב במקום המשחקים...

Based on the sources brought within and the Pesak above, in our case it would be Assur to be Matir Reuven's Neder not to eat pig. Both of points 1 and 2 from the question seem to be addressed in the above Teshuva, and the answer is not to be Matir this, for these reasons.

If someone was Matir this Neder, that is a separate Halachic discussion as to whether it is valid, and not the topic of this post.

For MY users that appreciate "easter eggs" in Shu"t Sefarim, it would be worth it to read the final two paragraphs of his Teshuva, Beer Moshe 165:12.

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