I should probably break this post into different ideas instead of one big jumble, but hopefully lumping everything together doesn't ruin it.
Nedarim 32a
אמר רבי אבהו אמר רבי אלעזר מפני מה נענש אברהם אבינו ונשתעבדו בניו למצרים מאתים ועשר שנים מפני שעשה אנגרייא בת"ח שנאמר וירק את חניכיו ילידי ביתו
M'mah nafshach: If Avraham was justified in going to war to save Lot, it is a milchemet mitzvah and there should be no penalty for taking talmidei chachamim to battle. If there was no justification, then Avraham himself should be culpable for fighting, even if no one else was involved.
This question requires a halachic explanation (It is important to note that the rule is that everyone fights in a milchemet mitzvah. It's this gemara that requires an explanation. Using this as a prooftext to argue that yeshiva students are exempt from the draft, putting side whether a 20 year old yeshiva bachur is really what is meant by "tamid chacham" in this context, confuses the rule with the exception. Aside from the fact that this is an aggadita, it is just one of three views quoted in that gemara, there is also an interesting Shita M'Kubetzet which explains that אנגרייא means unpaid volunteer (אנגרייא = אין אגרא). The problem is that Avraham did not pay his soldiers properly, not in the fact that he took them to war with him.), R' Chaim Elazari at least provides us with a moral explanation. Regarding Lot's being saved from Sdom, Ramban writes in next week's parsha (19:29):
ויזכור אלקים את אברהם וישלח את לוט – ענין הכתוב הזה כי לוט נתחסד עם הצדיק ללכת עמו לשוט בארץ באשר ילך, והוא שנאמר: וילך אתו לוט (בראשית י״ב:ד׳) כי לצוות שלו הלך, ולכן היה לו זכות להצילו בזכות אברהם, כי בעבורו הוא גר בסדום, ולולי אברהם עודנו היה בחרן עם מולדתו, ולא יתכן שתבא אליו רעה בעבור אברהם שיצא במצות קונו. וגם זה היה הענין ששם אברהם נפשו בכפו לרדף המלכים בעבורו.
Lot did not have to leave home and travel to Eretz Yisrael with Avraham. He voluntarily took it upon himself so that Avraham would have a travelling companion. True, Lot have made some bad choices that led to his being in Sdom, but it all started with a good choice -- to follow Avraham on his journey. If not for having taken that first step, he would be safely ensconced in his home in Charan and in no danger at all.
That first step was for the sake of the tzadik Avraham; therefore, Lot deserved in return to be saved in the merit of Avraham and not suffer on his behalf.
Avraham's obligation to save Lot was not m'din milchemet mitzvah, but m'din hakarat ha'tov. Since Lot went out of his way for Avraham, Avraham owed him something in return. No one else among Avraham's followers had a similar obligation; therefore, Avraham should not have involved them in this war.
The flipside of this Ramban is the Ramban's justification of לֹֽא־יָבֹ֧א עַמּוֹנִ֛י וּמוֹאָבִ֖י בִּקְהַ֣ל ה׳ (Devarim 23:9): והנראה אלי כי הכתוב ירחיק שני האחים האלה שהיו גמולי חסד מאברהם, שהציל אביהם ואמותם מן החרב והשבי, ובזכותו שלחם השם מתוך ההפכה והיו חייבים לעשות טובה עם ישראל, והם עשו עמהם רעה
Maharal in Gevuros Hashem ch 9 offers a different explanation of what the gemara means to suggest. Maharal faults Avraham for a lack of bitachon. If he needed to raise an army, he should have enlisted the help of professional soldiers, not talmidei chachamim who had no prior training in battle. Doing so reeks of desperation, lack of faith, and that is what Avraham is faulted for. The punishment of galus is a tikun, as it would serve as the means for Avraham's descedents to aquire more perfect faith in Hashem.
Hold that thought in mind for a little while as we make a little detour...
וַיֵּחָלֵ֨ק עֲלֵיהֶ֧ם ׀ לַ֛יְלָה ה֥וּא וַעֲבָדָ֖יו וַיַּכֵּ֑ם (14:15)
Rashi explains al pi pshat the the pasuk's words are out of order. The word וַיֵּחָלֵ֨ק applies to ה֥וּא וַעֲבָדָ֖יו; meaning, Avraham and his men divided themselves so as to lead a two pronged attack.
Rashi then quotes a Midrash:
ומדרש אגדה: שנחלק לילה, ובחצות ראשון שלו נעשה לו הנס, וחציו השיני נשמר ובא לחצות לילה של מצרים
It was the night that was divided in two. In the first half, there were miracles done to enable Lot to be saved and Avraham to win the war. The second half of the night was also primed for miracles, but those would only happen at the time of yetzi'as Mitzrayim.
Is there a shortage of nights that can be used for miracles? We can only give Avraham half a night or miracles, because we need to hold the other half in reserve for Bn"Y in the future? Why not give Avraham the whole night, and in the future give Bn"Y some other whole night so that things don't need to be divided up?
R' Mordechai Eliyahu explained that what Rashi/Chazal are trying to tell us is that Lot did not really deserve a miraculous victory to be done on behalf of his being saved. Having abandoned Avraham for the pleasures of Sdom, he had allied himself with the wrong team. He was saved only because he rode the coattails of Avraham Avinu, so to speak.
In reality, that night was a night of miracles only because Bn"Y would need it to be so in the future. However, once is was going to be a night of miracles anyway, Hashem skimmed off a little and gave something to Lot. All boats rise with the tide, whether they deserve it or not.
In a similar vein, there were three angels sent to Avraham (18:3) מיכאל, וגבריאל, ורפאל, מיכאל שבא לבשר את שרה, רפאל שבא לרפאות את אברהם, גבריאל דאזיל למהפכיה לסדום Rashi adds that the angel who came to heal Avraham was the same angel that later saved Lot from Sdom. Here too, one might ask: is there a shortage of angels upstairs? Why not send another angel to fulfill the mission of saving Lot?
R' Mordechai Eliyahu says this is the same idea. Lot rides Avraham's coattails. He did not have enough zechyus to merit earning his own angel, but once one came for Avraham, he was saved as well.
Perhaps one can answer the original question a little differently.
Rashi writes that the two sheep which Rivka prepared for Yaakov to serve to Yitzchak on the night he intended to bless Eisav were the korban pesach and korban chagigah. I once quoted Malbi”m who explains that Pesach is the time when we reach l’ma’alah min ha’teva. There is no way barring supernatural intervention that Klal Yisrael could have escaped the bondage of Mitzrayim and there was no way based purely on merit that we deserved to escape. “Halalu ovzei avodah zarah v’halalu ovdei avodah zarah.” Pesach means destiny trumps zechuyus/chiyuvim. The bracha of the Avos that Yitzchak was going to pass on was a bracha that transcended any and all obstacles.
The famous vort is "pasach Hashem al ha'pesach," even though normally Hashem says pischu li at least a pesach shel machat, on leil ha'seder Hahsem is even willing to forgo that. This is why Eisav thought he had a shot at those brachos. When you are not counting merits/demerits, anything is possible.
Perhaps this is why Lot was able to merit being saved that night as well. Had it been any other night, all bets would be off, but leil ha'seder is different. Lot could experience his own personal "yetzi'as Mitzrayim" and be rescued from captivity even if unworthy because that night is a night like no other.
All this is well and good, but When I took a peek at the language of the Midrash Rabbah that Rashi is based on, my impression of what's going on here changed.
וַיֵּחָלֵק עֲלֵיהֶם לַיְלָה – רַבִּי בִּנְיָמִין בַּר יֶפֶת מִשֵּׁם רַבִּי יוֹנָתָן הַלַּיְלָה נֶחְלַק מֵאֵלָיו. וְרַבָּנָן אָמְרֵי יוֹצְרוֹ חִלְּקוֹ, אָמַר הַקָּדוֹשׁ בָּרוּךְ הוּא אֲבִיהֶם פָּעַל עִמִּי בַּחֲצִי הַלַּיְלָה, אַף אֲנִי פּוֹעֵל עִם בָּנָיו בַּחֲצִי הַלַּיְלָה. וְאֵימָתַי בְּמִצְרַיִם, שֶׁנֶּאֱמַר: וַיְהִי בַּחֲצִי הַלַּיְלָה וַה׳ הִכָּה כָל בְּכוֹר וגו׳ (שמות י״ב:כ״ט).
אָמַר רַבִּי תַּנְחוּמָא אִית דְּמַפְקִין לִישְׁנָא אַחֲרִינָא אָמַר הַקָּדוֹשׁ בָּרוּךְ הוּא אֲבִיהֶם יָצָא בַּחֲצִי הַלַּיְלָה אַף אֲנִי אֵצֵא עִם בָּנָיו בַּחֲצִי הַלַּיְלָה, שֶׁנֶּאֱמַר: כֹּה אָמַר ה׳ כַּחֲצֹת הַלַּיְלָה אֲנִי יוֹצֵא (שמות י״א:ד׳).
R' Mordechai Eliyahu's approach is that Hashem was going to do miracles for Bn"Y anyway, so he threw some miracle power Lot's way as well. According to the Midrash, aderaba, it's the reverse -- Hashem did miracles for Bn"Y on this night because of what Avraham did! It's not an absolute proof, but look at the order in which things occurred: if Lot is riding the coattails of the future miracles for Bn"Y, then shouldn't the first half of the night be dedicated to those miracles, as they are primary, and Lot get the second half, the leftovers, similar to how the malach came to heal Avraham as its primary mission and then only secondarily went on to save Lot? From the fact that the first half is dedicated to Lot, it seems that is primary, and what happened in Mitzrayim is secondary.
What bothers me about this Midrash is the idea of הוּא אֲבִיהֶם פָּעַל עִמִּי בַּחֲצִי הַלַּיְלָה. Those words פָּעַל עִמִּי makes it sound like Avraham was acting for Hashem's sake. Wasn't he acting for Lot's sake? For his family's sake?
I don't know if I have a good explanation, but let me try. I want to revisit something I wrote 10 years ago. At the end of the pasuk וַיִּקְח֨וּ אֶת־ל֧וֹט וְאֶת־רְכֻשׁ֛וֹ בֶּן־אֲחִ֥י אַבְרָ֖ם וַיֵּלֵ֑כוּ the Torah adds וְה֥וּא יֹשֵׁ֖ב בִּסְדֹֽם. We already know Lot was living in Sdom. Why stick that in again here? I suggested is that the Torah is telling us that Lot had no regrets. "Put yourself in Lot's shoes: you left Avraham to go move to greener pastures, and suddenly you find yourself in the midst of a war, taken hostage, and all the wealth you had accumulated thanks to Avraham gone. What would be going through your mind? I know what I would be thinking. I would be imagining the quiet evenings sitting in an armchair in Avraham's tent and kicking myself for turning my back on that." That's not what Lot thought. וְה֥וּא יֹשֵׁ֖ב בִּסְדֹֽם -- his mind was still fixated on his home in Sdom, happy to be where he was, irrespective of what had occurred.
R' Shlomo Kluger suggests this pshat, but then he suggests something different, 180 degrees the opposite, and I am going to put a slight twist on what he says while keeping the basic idea. The reason Lot was calm and at peace with where he was is not because he was so steeped in the culture of Sdom that he was incapable of regret, but aderaba, it was because he still had faith. His bitachon was intact. Even though he knew he was in Sdom, the bottom of the barrel, he was confident, whether because of something he had done or in the merit of Avraham, that he would be saved.
רַבִּ֥ים מַכְאוֹבִ֗ים לָ֫רָשָׁ֥ע וְהַבּוֹטֵ֥חַ בַּֽה׳ חֶ֝֗סֶד יְסוֹבְבֶֽנּוּ (Teh 32:10). The Yalkut explains that the seifa of the pasuk is referring to the same rasha as the reisha: רבים מכאובים לרשע. רבי אליעזר ורבי תנחום בשם רבי ירמיה אפילו רשע ובוטח בה׳ חסד יסובבנו. You can be a Lot who has turned his back on Avraham and gone to Sdom, but so long as you have bitachon left, Hashem will not abandon you.
Did Avraham want to save Lot because he was family? Imagine you had a nephew like Lot who turned his back on you after you had given him everything, who walked away from everything you valued, who chose a lifestyle antithetical to your entire belief system. Is that the guy you are going to endanger your life to save? Blood is thicker than water, but ad k'dei kach?!
Maybe it's not family ties that motivated Avraham to go to bat for Lot. פָּעַל עִמִּי means Avraham on a personal level may have wanted nothing to do with Lot, but for the sake of doing good l'shem Shamayim, since he recognized Lot as a fellow man of faith (albeit on a far lower level), Avraham put aside his personal feelings and came to Lot's rescue. In turn, Hashem put aside all the many faults of Bn"Y and granted them miracles upon miracles in leaving Egypt.
You didn't forget how I started this post I hope : ) Perhaps this is the context that helps us better understand and appreciate Maharal's view that Avraham is held accountable here for taking talmidei chachamim to war because it showed a lack of bitachon. The whole justification for the war here is an outgrowth of the bitachon of Lot, of a rasha. When someone like that rises to the occasion and shows that in his heart of hearts he still has faith, how much more so is it incumbent upon Avraham Avinu, the tzadik, to rise to an even higher level in his bitachon. That's why Hashem was so medakdeik here on Avraham.
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