Most of the second half of the book of Genesis is about Yakov’s children, with a strong focus on Yosef. Yet, right in the middle of the Yosef narrative, the Torah interrupts with a cryptic parallel side story about Yehuda. It’s commonly glossed over as it’s content is perhaps a little awkward.

Yehuda has a son who displeases God and dies. Presuming some form of levirate marriage, wherein marriage outside the clan is forbidden, Yehuda’s second son marries Tamar, but refuses to do his duty and have a child with her, so he dies as well. Fearing that Tamar was somehow killing his sons, Yehuda withheld his third son from her, leaving her in limbo as the first chained woman – aguna. The story continues that she pretended to be a harlot to seduced Yehuda, and became pregnant.

When word spread that Tamar was pregnant, the natural presumption was that she had violated the prohibition of staying within the clan, and she ought to be executed. Only at the last minute, she revealed her ruse, and Yehuda admitted fault.

What is this story doing in the middle of the Yosef story?

R’ Jonathan Sacks observes that this story mirrors the Yosef story, and illustrates that Yosef and Yehuda had a parallel rise and fall.

Both stories involve deception through clothing – Yosef with his blood-stained tunic, and Yehuda with Tamar’s seductive disguise.

The way the Torah begins this narrative is that Yehuda was isolated:

וַיְהִי בָּעֵת הַהִוא וַיֵּרֶד יְהוּדָה מֵאֵת אֶחָיו וַיֵּט עַד־אִישׁ עֲדֻלָּמִי וּשְׁמוֹ חִירָה. וַיַּרְא־שָׁם יְהוּדָה בַּת־אִישׁ כְּנַעֲנִי וּשְׁמוֹ שׁוּעַ וַיִּקָּחֶהָ וַיָּבֹא אֵלֶיהָ – And afterward, Yehuda descended from his brothers and camped near an Adullamite whose name was Hirah. There Judah saw the daughter of a certain Canaanite whose name was Shua, and he married her and lived with her. (38:1, 2)

Yehuda’s descent was both literal and figurative – וַיֵּרֶד יְהוּדָה מֵאֵת אֶחָיו – the Midrash teaches that the remaining brothers held Yehuda responsible for their father’s misery. He separated himself and did what no one else in the family had done – he married a Canaanite.

The turning point in this story is powerful, where Tamar reveals that she fulfilled her duty to the clan when the family would not fulfill theirs:

הִוא מוּצֵאת וְהִיא שָׁלְחָה אֶל־חָמִיהָ לֵאמֹר לְאִישׁ אֲשֶׁר־אֵלֶּה לּוֹ אָנֹכִי הָרָה וַתֹּאמֶר הַכֶּר־נָא לְמִי הַחֹתֶמֶת וְהַפְּתִילִים וְהַמַּטֶּה הָאֵלֶּה. וַיַּכֵּר יְהוּדָה וַיֹּאמֶר צָדְקָה מִמֶּנִּי כִּי־עַל־כֵּן לֹא־נְתַתִּיהָ לְשֵׁלָה בְנִי וְלֹא־יָסַף עוֹד לְדַעְתָּה – As she was being brought out, she sent this message to her father-in-law, “I am with child by the man to whom these belong.” And she added, “Examine these: whose seal and cord and staff are these?” Judah recognized them and said, “She is more in the right than I since I did not give her to my son Shelah.” And he was not intimate with her again. (38:25,26)

As surely as Yosef and Yehuda hit their rock bottoms, they could both rise again.

Admitting his wrongdoing, he could now make amends, and the man who had proposed murdering Yosef could find his way back to become the man who would volunteer to stand in for Binyamin when Binyamin was in danger.

Parenthetically, it is worth noting that Tamar took an enormous gamble to avoid embarrassing Judah. Chazal hyperbolically liken humiliating someone to murder. R’ Jonathan Sacks quips that we cover bread at the Shabbos table so that we don’t embarrass the bread when we make kiddush first; if only we would be so careful with people with feelings!

R’ Jonathan Sacks notes throughout the Yosef story that it contains the first instances of teshuva – repentance and forgiveness, healing what would otherwise lead to permanent fractures in family relationships. Yakov’s family could find their way back once they could admit their mistakes to themselves and each other, and so can we.

One of the most tragic figures in the Torah is Reuven. His haunting story is replete with squandered potential and the road not traveled. When he wanted to bring his mother flowers, he might have waited until Leah was alone. After Rachel’s death, he might have spoken directly to his father instead of moving the beds.

One of his defining missed opportunities is when the brothers resolved to dispose of Joseph, and Reuven convinced them to change their scheme:

וַיִּשְׁמַע רְאוּבֵן, וַיַּצִּלֵהוּ מִיָּדָם; וַיֹּאמֶר, לֹא נַכֶּנּוּ נָפֶשׁ. וַיֹּאמֶר אֲלֵהֶם רְאוּבֵן, אַל-תִּשְׁפְּכוּ-דָם–הַשְׁלִיכוּ אֹתוֹ אֶל-הַבּוֹר הַזֶּה אֲשֶׁר בַּמִּדְבָּר, וְיָד אַל-תִּשְׁלְחוּ-בוֹ:  לְמַעַן, הַצִּיל אֹתוֹ מִיָּדָם, לַהֲשִׁיבוֹ, אֶל-אָבִיו – But when Reuven heard, he tried to save him from their clutches. He said, “Let us not take his life.” And Reuven went on, “Shed no blood! Cast him into that pit out in the wilderness, but do not touch him yourselves”—intending to save him from them and restore him to his father. (37:21, 22)

Yet his good intentions never materialize:

וַיָּשָׁב רְאוּבֵן אֶל-הַבּוֹר, וְהִנֵּה אֵין-יוֹסֵף בַּבּוֹר; וַיִּקְרַע, אֶת-בְּגָדָיו.  וַיָּשָׁב אֶל-אֶחָיו, וַיֹּאמַר:  הַיֶּלֶד אֵינֶנּוּ, וַאֲנִי אָנָה אֲנִי-בָא – When Reuven returned to the pit and saw that Joseph was not in the pit, he rent his clothes. Returning to his brothers, he said, “The boy is gone! Where do I go now?” (37:29, 30)

R’ Shamshon Raphael Hirsch wonders whether his previous failures might have crippled him, or that he felt threatened by Joseph; what is certain is that by deferring action to avoid the tension of confrontation, the moment fizzled out and disappeared.

The Midrash laments the missed opportunity, saying that if Reuven had known that the Torah would record for posterity that “when Reuven heard, he tried to save him from their clutches”, he would have carried Joseph back to his father on his shoulders; and the Midrash concludes with the lesson that we should do everything wholeheartedly.

But if you think about it, that’s the wrong message. If Reuven would act because of his audience, he wouldn’t be saving Joseph because he cared at all! Isn’t the Midrash honing in on the wrong point?

R’ Elya Meir Bloch observes that since the Torah spans centuries and generations, it has time skips. The stories and sagas that make the cut resonate not just in the protagonist’s lives, but in the lives of their readers for all time.

R’ Shlomo Farhi teaches that we can never know which moments in our lives are the inflection points. The Midrash is not about insincerity; it’s about indecisiveness. If we knew which moments would be the ones that mattered, we’d be fully present and engaged to give our all.

If Reuven had only known, says the Midrash. If he’d known that the future was watching that moment, he might have found the conviction to follow through. But Reuven could not know. He had not read the story. None of us can read the story of our life – we can only live it.

As R’ Jonathan Sacks notes, it is impossible not to recognize in Reuven a person of the highest ethical sensibilities. His heart is in the right place and he only means the best. But though he had a conscience, he lacked courage and conviction. He knew what was right, but dwelling on his mistakes had robbed him of the resolve to act boldly and decisively; and in this particular moment, more was lost than Joseph. So too was Reuven’s chance to become the hero he could and should have been.

The feeling of regret is the pain of what could have been. To minimize regret, engage in every moment wholeheartedly and fully present.

The future is watching.

During the famine in Canaan, Yakov sent his sons to Egypt to obtain provisions for their family. But they were arrested and imprisoned. Unbeknownst to them, their captor was their long lost brother Yosef. While in prison, they speculated how they’d wound up in their precarious situation:

וַיֹּאמְרוּ אִישׁ אֶל-אָחִיו, אֲבָל אֲשֵׁמִים אֲנַחְנוּ עַל-אָחִינוּ, אֲשֶׁר רָאִינוּ צָרַת נַפְשׁוֹ בְּהִתְחַנְנוֹ אֵלֵינוּ, וְלֹא שָׁמָעְנוּ; עַל-כֵּן בָּאָה אֵלֵינוּ, הַצָּרָה הַזֹּאת – The brothers lamented to each other, “We are guilty! For what we did to our brother… We saw his suffering! He pleaded with us, and we ignored him. We have brought this on ourselves!” (42:21)

But reviewing the entire episode as it unfolded, the story is simply about what they did to him. There is no record of Yosef saying anything to them, let alone pleading!

What were they talking about?

R’ Shlomo Freifeld powerfully suggests a frightening resolution.

Vision has two aspects. There is a physical aspect, governed by our eyes. But there also the mental aspect, governed by our minds. Lacking the physical aspect will result in literal blindness, lacking the mental aspect will result in figurative blindness. But the result is the same. You do not perceive.

In the brothers eyes, Yosef was trouble, and he had to go. It was settled in their minds. They were single-mindedly focussed solely on the task at hand of exiling Yosef. As the story unfolded in their minds eye, he was an object to be removed.

But is there any doubt that a third-party observer to this traumatic episode would have witnessed the victim crying and pleading? But the Torah records the story from the actor’s perspective. Powerful emotions had dulled their sensitivity. Caught up in the heat of the moment, he hadn’t made a sound in their eyes.

Only in hindsight, sitting in jail years later, could they take stock of the terrible ordeal as it truly happened.

It’s scary because our minds corrupt our vision to conform to our biases.

And your eyes are useless when your mind is blind.