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It is always possible to pick on even the most inspirational stories, but hopefully in doing so we end up learning something. The Talmud relates this story:

Hillel the Elder worked every day to earn half a dinar, half of which he would give [as tuition] at the study hall… One time he did not find employment… and the guard did not let him enter. He went up to the roof, and sat at the edge of the skylight to hear the words of the living God from the mouths of [Rabbis] Shemaya and Avtalyon. It was Shabbat eve … Snow fell upon him from the sky… Shemaya and Avtalyon [noticed that less light was entering the study hall], went up, and found him covered with snow three cubits high. They freed him, washed him and smeared oil on him, and sat him opposite the bonfire to warm him. They said: This man is worthy for us to desecrate Shabbat for him. [Yoma 35b]

(1) Was Hillel stealing, by listening to lectures without paying? Why did he not simply ask for permission as a charity case, or ask for a loan?

(2) The rescuers said: "This man is worthy for us to desecrate Shabbat for him." Does that mean that for someone deemed less worthy we should not try to save him on Shabbat?

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The second question is posed by the Ein Yakov, who writes the following:

דאף שהיה ערב שבת, ועל פי רוב מתגבר הקרירות בערב שבת, ונתנו העולם סימן 'וקרקר כל בני שת' וגם תקופת טבת דרכו להיות גובר הקרירות, ואפילו הכי סיכן עצמו בשביל אהבת התורה, וסמך עצמו אמה דכתיב (קהלת ח, ה) 'שומר מצוה לא ידע דבר רע'. והשתא מדוקדק שאמרו: 'ראוי זה לחלל עליו את השבת', דלכאורה קשה, מאי שנא זה מאדם אחר, דהא אפילו משום תינוק בן יומו מחללין עליו את השבת, ומה רבותא דידיה דקאמר 'ראוי', אלא ודאי אפשר דבאחר הוי כמאבד עצמו לדעת, שלא היה לו להביא עצמו לידי סכנה כזו שיצטרך לחלל עליו את השבת, רק בזה, שעשה הכל לכבוד התורה, ראוי לחלל עליו את השבת אף בכי האי גוונא

Brief summary: In general, we do not desecrate Shabbos to save the life of someone who attempts suicide*. Ein Yackov assumes that one who climbs on a roof on Erev Shabbos in Teves as paramount to suicide, and would therefore not be eligibile for saving. However, since he was doing it for the sake of Torah, he invoked 'שומר מצוה לא ידע דבר רע' and it was permitted to save his life.


*This is not necessarily the accepted Halachah. For further sources about desecrating Shabbos to avert an attempted suicide, see Chochmas Shlomo (R Shlomo Kluger) to OC 329, and Shu"t Shevus Yackov #16. See also Minchas Chinuch 237:2 and Or Gadol #1). Practically, see Tzitz Eliezer ח"ח סי' טו קונ' משיבת נפש פ"ד who rules that one may desecrate Shabbos to save lives even in cases of suicide.

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Your first question is an interesting question which I haven't seen asked yet. As to the question why he didn't take a loan - perhaps he knew that it was highly unlikely that he would be able to pay back. Nor did he want to take charity as שונא מתנות יחיה. Perhaps the entrance fee was not charged for the right to learn there but to pay towards the heating- and upkeep costs of the learning hall. In that case, listening from the roof would not constitute theft. If you want to get more inspiration from this story, consider the following point made by the late Rav Zalman Rotbarg, the Rosh Yeshiva of Beis Meir in Bne Berak, and nephew (by marriage) of the Chazon Ish. He points to a רבינו יונה in שערי תשובה שער ב סימן כו (here https://hebrewbooks.org/pdfpager.aspx?req=52052&st=&pgnum=125 ) who explains the saying of הלל in אבות that אם אין אני לי מי לי to mean that it is never enough to listen to a lecture and think that you understand it. It requires a lot of thinking and drawing conclusions before it can become part of the person (עיין שם). Now הלל himself, must have been a tremendous listener if he managed to concentrate listening from the roof through a crack in the window (which in winter surely wasn't wide open) not even noticing that it was snowing! Nevertheless he told us that without constant contemplating, revision and stock-taking, anything you hear will not become internalized!

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