Yehudah's tefilah -- what took him so long?

The Midrash comments on the opening pasuk of our parsha, רַבָּנָן אָמְרֵי הֲגָשָׁה לִתְפִלָּה: וַיִּגַּשׁ אֵלִיָּהוּ הַנָּבִיא וַיֹּאמַר ה׳ אֱלֹקי וגו׳ (מלכים א י״ח:ל״ו).  This was not just a conversation between Yehudah and Yosef, but rather Yehudah was mispallel to Hashem that his brother Binyamin should be allowed to go free.  

Why, asks the Ostrovtza in Meir Einei Chachamim, did Yehuda wait until now to daven?  Why did he, or any of the other brothers, not daven to Hashem for help earlier, when Shimon was imprisoned by Yosef?  

My first thought when I saw this question is that of course Yehudah would daven now, as he put his own fate on the line in guaranteeing the return of Binyanim.  Were that true, it would be a very self-serving tefilah and not at all consistent with Yehuda's character or his words.  Yehudah offered to personally serve as a substitute for Binyamin.  He was willing to sacrifice himself for his brothers.  Surely his tefilah would come from that same spirit of self-sacrifice.

The Ostrovtza resolves the issue by taking us back to that episode of Shimon's imprisonment.  Why was it that only after three days in prison did the brothers finally admit  וַיֹּאמְרוּ אִישׁ אֶל⁠ אָחִיו אֲבָל אֲשֵׁמִים אֲנַחְנוּ עַל⁠ אָחִינוּ.  If, as Rashbam writes, this was מדה כנגד מדה, אנחנו השלכנוהו בבור והנה אנחנו נאסרים בבית השבי, shouldn't they have realized that on the first day when they were thrown  בבית השבי?  Secondly, when Yosef declared then אֲחִיכֶם אֶחָד יֵאָסֵר בְּבֵית מִשְׁמַרְכֶם וְאַתֶּם לְכוּ הָבִיאוּ שֶׁבֶר רַעֲבוֹן בָּתֵּיכֶם, the Torah tells us the brothers responded וַיַּעֲשׂוּ⁠ כֵן.  What exactly did they do?  They hadn't yet departed for home; they were still sitting in jail.  Lastly, what were Yosef's intentions in this whole charade?

Yosef was not out for revenge.  What he hoped to achieve was to cleanse his brothers of the horrible sin of his sale by bringing them to recognize and admit their error and do teshuvah.  We describe Hashem as זוכר כל הנשׁכּחות אתה  R' Shmelka m'Nikulsburg explains that if we forget about our sins, then Hashem will remember them and He will mete out punishment.  But if we are aware of our own wrongdoings and remember them ourselves, Hashem will forget about them because we will take care of doing teshuvah.  How does a person come to awareness of that which he does not remember of recognize as a sin?  The answer is that Hashem does us a favor -- the punishment always parallels the crime, midah k'neged midah.  Yosef acted in the same way, of leading his brothers down the path of midah k'neged midah to come to self-awareness.

First, Yosef accused them to being spies, מרגלים. Rashi comments on לא תלך רכיל that אני אומר על שם שכל משלחי מדיינים ומספרי לשון הרע הולכים בבתי רעיהם לרגל מה יראו רע או ישמעו רע לספר בשוק, נקראים הולכי רכיל, הולכי רגילה.  Since the brothers had accussed Yosef of spreading rechilus and tattling on them to Yaakov, he accused them of being מרגלים in the hope that they would get the message.

Three days of thinking it over were not enough, so Yosef made a deal that he would let them go provided one of them stayed behind.  The catch is that they, not he, would have to choose the one.  The Yerushalmi in Terumos (end of ch 8) writes that if the aku"m demand that one person of a group be turned over, we are not permitted to do so.  However, if it is clear that only one member of the group is culpable, he can be selected, e.g. Yonah being thrown overboard because he was the cause of the storm.  Yosef was forcing the brothers to make a choice -- you are being punished for doing wrong; figure out what you did and who the guilty party is among you (see Meshech Chochma who also refers to this Ylmi in the context of these pesukim but uses it a bit differently).  וַיַּעֲשׂוּ⁠ כֵן!  The brothers realized that it was the sale of Yosef that was the cause of their sorrows and the finger was pointed at Shimon, who they turned over.  This realization that they did something wrong prompted the brother's declaration  וַיֹּאמְרוּ אִישׁ אֶל⁠ אָחִיו אֲבָל אֲשֵׁמִים אֲנַחְנוּ עַל⁠ אָחִינוּ אֲשֶׁר רָאִינוּ צָרַת נַפְשׁוֹ בְּהִתְחַנְנוֹ אֵלֵינוּ וְלֹא שָׁמָעְנוּ עַל⁠ כֵּן בָּאָה אֵלֵינוּ הַצָּרָה הַזֹּאת

Yosef was not done.  אֲשֵׁמִים אֲנַחְנוּ means that "mistakes were made."  You bring a korban asham if you made a mistake and accidentally ate cheilev or violated a different issur kareis.  The brothers needed to do teshuvah for the intentional act of selling Yosef and not just pass it off as a mistake.  Therefore, Yosef planted his goblet, obviously an intentional act, to entrap Binyamin, midah k'neged midah just as the brothers had intentionally acted against him.

Yehudah says at the end of last week's parsha  הָאֱלֹקים מָצָא אֶת⁠ עֲוֺן עֲבָדֶיךָ.  A metziya means something lost which was now discovered. זוכר כל הנשׁכּחות אתה  Yehudah understood that until this point, they had not truly uncovered, discovered, realized and remembered all the wrong they had done. It was still b'geder הנשׁכּחות.  Now the full truth was revealed.    

Says the Ostrovtza: whatever tefilah Yehuda or the brothers had offered until this point would not have counted as tefilah.  It would be like toveil v'sheretz b'yado.  Prayers for relief can be accepted only after a person accepts responsibility for their own wrongs that led to the crisis at hand.  Therefore, it was only at this point, after the entire process of teshuvah was complete, that the Torah describes Yehudah as entering הֲגָשָׁה לִתְפִלָּה.

I only quoted the opinion in the Midrash that Yehudah was engaged in tefilah, but there is another view thay says he approached seeking to do battle, and another approach that says he approached in piyus, supplication.  Perhaps it was all three:   רַבִּי אֶלְעָזָר אָמַר פְּשַׁט לְהוֹן אִם לְמִלְחָמָה אֲנִי בָא, אִם לְפִיּוּס אֲנִי בָא, אִם לִתְפִלָּה  The Ostrovtza reads this like the stages of grief.  When something goes wrong, first there is the battle stage -- you want to fight G-d and argue that you are right and deserving and He is wrong.  Next comes the stage of piyus, negotiation -- you tell yourself that what you did was not so bad, that you've done plenty of good deeds to offset the wrong.  Finally there comes the stage of acceptance, where you understand the wrong that was done and come to regret it.  This is the stage of tefilah, where one can once again come close to Hashem in supplication and ask for forgiveness.