Weekly Parsha Review Laced with Humor and Sarcasm from The Oisvorfer Ruv

Vayeshev 2025: The Less-Than-Holy, Less-Than-Perfect, Yet Selected Few

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Raboyseyee and Ladies,

The Less-Than-Holy, Less-Than-Perfect, Yet Selected Few:

This week’s parsha post is brought to you by Delta Airlines, which the heylige Ois flew on his way -along with the eishes chayil- to Los Angeles to visit with our West Coast branch and most of what you are reading was taka written during the six- and one-half hour flight.

We begin where we would typically end, with the bottom line: REALITY TV AIN’T GOT NOTHING ON PARSHAS VAYESHEV. One could convincingly argue that the heylige Toirah -specifically this week’s parsha, inspired reality TV. In fact, the same is true of the entire Sefer Bereishis, and with that introduction, welcome to the Yaakov Ovenu family. They are the most dysfunctional family in all of Sefer Bereishis -though Yitzchok and Rivka’s family are in the hunt for 2nd place. Did the heylige Ois shock you? And yet it’s all emes! There’s more! One might argue -with some very good support, that this sort of rampant dysfunction is davka why the RBSO loved, and loves them anyway. More on that theme interspersed below.

Chevra, buckle up. Because while you’re thinking that today’s fractured families, blended households, sibling rivalries, lawsuits between cousins, and WhatsApp fights with in-laws, are the epitome of dysfunction, the Heylige Toirah says: “Hold my beer.”

Welcome to the house of Yaakov Ovenu — the original Jewish family. They were not the picture-perfect mishpocho we draw in coloring books. Theirs did not feature a serene Shabbis tish with everyone smiling, singing z’mirois, helping set and clear the table, reading from the Little Medrish while wearing their white Shabbis shirts. No. This family was on fire — and not in the tzaddik sense.
More like:

  • Four wives
  • Twelve kids
  • A daughter with a traumatic episode
  • Brothers who violently avenge her
  • One son who dreams of superiority
  • Ten who can’t stand him
  • A kidnapping
  • A sale
  • A faked death
  • A decades-long lie
  • Jealousy
  • Lust
  • Swords
  • Two son who went on a killing spree
  • Mandrakes
  • Idols
  • Deception
  • Another son who seemingly slept with one of his stepmother’s
  • And one who rose to become viceroy of Egypt despite zero time in yeshiva and a prison record.

Ladies and gentlemen, despite what you read above -which is all emes and is described vividly in the heylige Toirah itself, these very people were the founding family of Klal Yisroel, the future Yiddin. And they were -as titled above- The Less-Than-Holy, Less-Than-Perfect, Yet Selected Few.

Let’s get real: many a family has that one son or daughter who is different. Some might say they are off the derech (OTD), some might even call that one the prodigal child, ober in the Yaakov Ovenu family, it does epes appear that each one of his boys with the exception of Binyomin, was a shtikel or more rogue. What’s happening here? Is this not the definition of a dysfunctional family? Shoin, I can already envision the emails and name calling, maybe even a call from a rabbi or two, but am I wrong? The emes is that they know what the Ois is writing is emes; the difference is azoy: they can only think it while the Ois can write it.

That all said, efsher you’ve been wondering why the RBSO chose davka this motely group. Why not a nice family without all this controversy. One would think the RBSO would have selected for greatness people who were squeaky clean, without controversy. Ober the reality is quite different. In fact, it’s mamish farkert! And the big question is this: does good behavior, and a perfect resume disqualify one to lead and or to be selected? Are good families disqualified? It’s mamish deep!

Let’s begin with the obvious: Yaakov’s marriage situation was at the least mamish unconventional. One husband. Four wives. Zero peace.

  • Rochel wanted babies.
  • Leah wanted love.
  • Bilhah wanted legitimacy.
  • Zilpah wanted recognition.
  • Yaakov wanted a nap and day off!

This wasn’t just dysfunction — it was mamish a holy soap opera. Each birth became a theological press conference: “Hashem saw!” “Hashem heard!” “Now my husband will love me!” “This time I will thank Hashem!” In the end, twelve sons born into four separate maternity wards, each with emotional undercurrents deep enough to drown a nation. One night Leah goes out to greet Yaakov with a deal that would make today’s transactional marriages blush: Tonight you’re mine — I bought you with dudaim. We have previously discussed Yaakov’s very busy marital schedule, which seemingly included mandrake bartering. Shoin. Where do we file this? Under “Shalom Bayis”? Under “Fertility Economics”? Or, under “Things They Don’t Teach in Sem”?

Meanwhile Rochel — beloved, righteous Rochel — steals her father’s gods, lies about it, and sits on them. She is forever known and beloved to us as “Mama Rochel,” but let us recall that she was not totally innocent when allowing her sister to bed Yaakov on their wedding night. According to some, she gave Leah the secret signs Yaakov and Rochel had prepared. According to others, Rochel was in the bedroom under the bed while Yaakov was topping off Leah. One cannot make this stuff up and these very ideas are brought to us by very famous and respected Sages. The bottom line: If you think your family has drama, remember: Yaakov had to juggle four competing wives, supernatural fertility tools, swapped beds, and thunderous emotions — and still had to get up in the morning to shepherd sheep.

Now let’s talk about the givaldige boys. When Dinah was violated (last week’s parsha), Shimon and Levi — age 13 — didn’t write angry letters to the editor. They didn’t ask Yaakov for a beis din psak (ruling). They didn’t organize a peaceful protest. They took their bar mitzvah swords and wiped out an entire city. Were they “loose cannons?” Were they but teenagers with righteous fury and absolutely no impulse control? And Yaakov’s response? Not: Really?! Not “Boys, that was wrong.” But: “You made me smell bad to the locals.” Shimon and Levi answered like Sicilian mafia dons: “Shall he treat our sister like a harlot?” Holy? Not exactly. But passionate, fiercely loyal, action-oriented, and ultimately the roots of the tribe of Levi, Kehuna (priesthood), Moishe Rabbeinu, Pinchas -another zealot and master of the spear who went on to kill Kozbi and Zimri. Let’s not forget Eliyahu. What does all this add up to? What have we here? Once again: The Less-Than-Holy, Less-Than-Perfect, Yet Selected Few. Did their behavior affect them? A nechtiger tug (fuhgeddaboudit).

Ober, let us -for a few paragraphs, zero in on the action in this week’s parsha where the bottom line is this: Yaakov’s kids were serial liars, kidnappers, and above all, expert gaslighters! Shoin I said it. Who does this? Their actions caused our Sages and many other exegetes to work overtime finding different defenses to their indefensible actions.


And before we get to Yehuda and his shenanigans, let’s quickly check out the events of Yoisef’s kidnapping. Ten grown men — the later to be known Shivtei Koidesh (the RBSO’s holy tribes) conspired to:

  1. Kill Yoisef.
  2. Change their minds.
  3. Sold him into slavery.
  4. Declared him dead.
  5. Dipped the coat in goat blood, the great coverup.
  6. Handed it to Yaakov like they just discovered a sock in the laundry.
  7. Watched their father collapse in grief.
  8. Said nothing for 22 years.

OMG! These are not kids who forgot to tell you they dented the car. These are Olympic-level emotional terrorists. And yet — they became the bedrock of the Jewish tribal system.  Says the Ramban (Bereishis 37:18): the brothers planned to kill Yosef:

וְנִתְחַכְּמָה לוֹ – כָּל אֶחָד מֵהֶם נָתַן עֵצָה לְהָמִיתוֹ.” And this on posik 20:   it was a real murder plot. “כַּוָּנָתָם לְהָמִיתוֹ הָיְתָה בְּלֹא סָפֵק.”

Raboyseyee, the Ois has said these many times over the past sixteen years: if this is not divine irony, nothing is. Ober, is the heylige Ois mamish an apikoires (heretic) and worse for stating his opinion on these matters? Is he a lone wolf? We shall address that later.

But wait, our parsha has more to give. Yet more individual stories which shine a not so flattering light on the behavior of Yaakov’s kids, some avada more than others, and let’s revisit with Yehudah, the man who almost had Tamar – his own daughter-in-law burned alive. Mistama she was hot before, but this would have put her over the top. Let us recall that one of her deceased husbands refused to finish his business inside of her davka because he didn’t want to mar her beauty. FYI: so says Rashi, I’m just repeating!

Let us spend some time on Yehudah, the man who proves that leadership is earned through struggle, mistakes, and passion — not perfection. Yehudah isn’t perfect; farkert: he is the poster child of Divine scandal. The heylige Toirah (Bereishis 38:1) tells us this: “Vayered Yehudah” — he went down. Rashi and others tell us that he went down socially, morally, and in family leadership. Rashi also says that he went down in his finances; he was down on his luck. He was demoted. His brothers didn’t trust him. Seemingly they weren’t happy with his plan to spare Yosief’s life and instead sell him to a pack of unknowing travelers into slavery. And yet, somehow, the Moshiach himself comes from the Yehudah line. Oh my! How is it that Yehudah, not the bechor (firstborn), and not the biggest tzaddik, becomes the ancestor of Moshiach. Ver veyst? Let’s look at his rap sheet, I meant, check his résumé:

  • Concocts the plan to Sells Yoisef to strangers-
  • Lies to Yaakov about it-
  • Marries a shiksa Canaanite woman-
  • Visits what he thinks is a roadside zoinah (spoiler: Tamar in disguise)-
  • Impregnates her-
  • Orders Tamar executed-

Another OMG! The story always bothered me. Yehudah, after cavorting with what he thought was a roadside service provider, discovers Tamar is pregnant and what does he do? He calls for her execution. Excuse me?! Was the service not up to his standards? What right did Yehudah have? What leg was he standing on? Never mind! Did Tamar swear an oath of celibacy? Was she under contract? Did she violate halacha? Was there even halacha yet? And who put Yehudah in charge of capital punishment? Hello, what about the RBSO; isn’t’ He in charge? Let’s set the record straight.

Fact #1: Yehudah had zero authority. The Toirah literally just said “Vayered Yehudah”—he was demoted. He wasn’t head of his family. He wasn’t head of anything. He was down and out, rejected by the brothers because of the Yoisef fiasco. Authority? The guy couldn’t even lead a caravan.

Fact #2: Tamar didn’t do anything wrong. She wasn’t married. She wasn’t betrothed. She was, halachically speaking, single and ready to mingle. The whole “she’s the daughter of Melchizedek the priest so she should’ve known better” is, to put it mildly, holy hogwash. Melchizedek wasn’t Jewish. There were no Kohanim. No priestly hierarchy. No churches. Nothing. Zero. Pure later midrash retrofitting holiness into pre-historic spreadsheets. Why medrish needed to gout of its way with all these bubamysehs (BS), ver veyst?

Tamar isn’t a saintly volunteer. She isn’t spinning yarn in a quiet corner. She’s bold, clever, morally audacious. She disguises herself, confronts Yehudah, and ensures the lineage that produces kings and Moshiach continues. She didn’t wait for the “perfect” brother-in-law to notice her. She acted strategically. And in doing so, she earns divine praise.  While Yehudah had her front, if you chap,  the RBSO had her back. Only in the heylige Toirah does scandal + audacity = righteousness. Gishmak! The bottom line: of course there is no logic here. This can only be explained as part of some masterplan the RBSO was involved with.

The bottom line: Tamar’s only “crime” was that she outsmarted Yehudah. And that’s not a crime; it’s a hobby in Tanach. And the Medrashic Whitewashing? Oy vey. A good number of midrashim twist themselves like pretzels trying to justify Yehudah’s death sentence as if Tamar somehow deserved it. No she didn’t. None of the pshat sources say she did. Yehudah acted impulsively, hypocritically, and stupidly. The heylige Toirah exposes it for what it was: male ego meeting moral myopia. And guess what? Tamar handled it with dignity, courage, and tact. No shouting. No exposure. No courtroom drama. Just: “Haker na.” Recognize, please… this signet ring that you, holy man, left behind.

In case you forgot, here’s what went down. Facing death by fire, she asked that the person with whom she consorted roadside, the very person who left a few personal items behind, recognize them. In that moment Yehudah crumbled and said the most honest line of his life: “Tzadkah mimeni”—she is more righteous than I. Finally, a moment of accountability. Yet despite all that, Yehudah – a proven riser, if you chap- rises again. Because he took responsibility, he became the template for righteous leadership. He learned from mistakes. Greatness doesn’t require perfection. It requires courage, humility, and accountability.  As an aside, lest you think the heylige Ois is off the reservation when he speak of the despicable acts committed by Yehudah and his bothers, the Sforno -on posik 38:26- says this about Yehudah’s admission when cornered by Tamar: Yehudah didn’t volunteer confession — he had no choice.

 “וַיַּכֵּר יְהוּדָה – הִכִּיר בֶּאֱמֶת כִּי לֹא הָיָה פֶּתַח תִּרוּץ.”

The bottom line: In the end, Yehudah is the spiritual ancestor of Dovid HaMelech? Who are we to argue? More on Dovid and his sex-capades another time but you get the point. Yehudah is a prime example of the Less-Than-Holy, Less-Than-Perfect, Yet Selected Few.

Our parsha also features everyone’s favorite Toirah personality, Yoisef, who finds himself tested, tempted, and avada traumatized. Let’s be honest: he was not the typical yeshiva bochur. Did he learn all day? No. Did he hang out with the girls? Yes. Did he strut in his multicolored coat like an influencer? Absolutely. Mrs. Potiphar tries to seduce him for months. Chazal say he almost gave in. They also discuss semen leakage through his fingers but that for another day. He held strong — but not effortlessly. Yoisef rises not despite his temptations, but because of them.

And the bottom line? It does appear that the RBSO likes humans who struggle and win — not sanitized saints. He may like them too, but it seems that He likes and selects for greatness, those who have some pep in their steps. And the Ois’ proof: Aside from the characters we have to date in Sefer Bereishis, let us take a very quick tour across Tanach:

  • Moishe killed an Egyptian-
  • Dovid messed up with Batsheva-
  • Rochov was a zoinah and becomes prototype of teshuvah-
  • Rus was a Moabite outsider-
  • Shlomo had 1,000 women and still wrote Koheles-

The list avada goes on and point made. The RBSO consistently chooses the flawed, the bold, and the messy. All humans but not the quiet perfect ones. Why is that? Ver veyst, as He never told us. What we do know is this: Perfection creates statues while flaws create stories, and stories create leaders. And that raboyseyee is good news for most us including avada the heylige Ois!

So yes — the family of Yaakov Ovenu was dysfunctional. Not mildly. Not quietly. But extravagantly. And yet — this is the family the RBSO chooses to build the Jewish people. Why? Because: Holiness is not the absence of mess. Holiness is what you build through the mess. Perfection is boring. Dysfunction is where the RBSO does His greatest work. The people of Jewish history, and the people who move it, are rarely the calm, quiet, “good boys and good girls.” They are the wild ones. The passionate ones. The impulsive ones. The heart-driven ones. The fighters. The lovers. The ones who make mistakes and learn from them. The ones who break the mold and then rebuild it. They are… THE LESS-THAN-HOLY, LESS-THAN-PERFECT, YET SELECTED FEW. My own father, OBM- said quite often about one of his own kids, “from wild ponies come thoroughbred prize winning horses.” May we learn from them. May we be inspired by them. And may we accept that our own messy families are not a bug in the system — they are the system.

The final bottom lines: “Chazal loved the Avos; who doesn’t,” and so they often tiptoed around the ugly. Rashi sugarcoats. Ramban hints. Sforno whispers. Ibn Ezra dodges. But the plain text?

For that let’s check in with Rav Yoel Bin-Nun who famously said this: “The plain text shows deep family dysfunction that midrashim sometimes avoid.” But who was he? So happens that is the founding father of the New Tanach Revolution. He co-founded Yeshivat Har Etzion (Gush) with Rav Amital, and was a central architect of the “Gush School” of Tanach — pshat-first, real-world psychology, no sugarcoating. His approach: “No halos — only human beings.”

  • The Avos make mistakes
  • The heylige Toirah wants you to see the mistakes
  • The moral lessons come precisely because they were flawed
  • The dysfunction is part of the divine plan, not an embarrassment

He’s one of the very few Orthodox scholars who openly writes this: The family of Yaakov was fractured, broken, jealous, competitive, angry, and at times immoral — and the heylige Toirah records this so we can learn from it.

So, the Yaakov family was a delightful dysfunctional mess. Boom! That’s not kefira or apikursis; that is honestly reading Tanach with both eyes open. So say I, and finally with some real support.

A gittin Shabbis!

The Heylige Oisvorfer Ruv

Yitz Grossman

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