He learned them in ways his forebears may not have, the painful nature of of their travails notwithstanding; it’s one of the major reasons the enduring messianic kingdom is ultimately established through him.
What did he do that they didn’t? And where was he effective where they might not have been?
One irony of the Yehuda narrative is that unlike the ostensible mistakes of his ancestors, which usually involve midrashic amplifications of what textually seem like minor infractions but are exegetically revealed to be actions that carry heavy spiritual consequences, Yehuda’s warts are blatantly narrated and are otherwise apparently exegetically blunted.
Starting with the sale of Yosef, his primary role in deceiving Yaakov and temporary loss of prestige as a result, going through his become an eminent personage among Canaanites, his sons’ rather sordid deaths, and the entire episode with Tamar.
Meanwhile, he has forced himself into a corner by essentially pledging himself as a surety for the return of Binyamin, in part as a penance for the sale of Yosef, but in part because, as the enforcer of the code of silence regarding the sale, he hasn’t left himself with a lot of room to maneuver.
However, starting with his admission in Chapter 38 and now with his effective carrot-and-stick approach with Yosef, Yehuda—having made his own mistakes—avoids the ones his ancestors made and not only succeeds in his mission but also catalyzes the first tribal reconciliation.
What mistakes did his forebears make?
Often in the interests of peace, they may have been too diplomatic; too much carrot, not enough stick.
Avraham and Yitzchak are criticized by Chazal for giving away too much in their dealings with the Avimelechs and the Philistines, who are portrayed as taking a lot more than they gave, even as both Avraham and Yitzchak recognized the extractive if not rapacious nature of the populations they were negotiating with.
Yaakov himself goes a step further before he meets his brother for the first time. He prepares on three tracks: prayer, militarism, and diplomacy. In fact his approach exemplifies almost the ideal response, even to the point that he is almost as worried that he will be forced to kill others as much as he or his over ones might be killed. Yet—while the material flattery detailed in Chapter 32 isn’t criticized—Yaakov’s self-reference as “your servant Yaakov” to Esav is viewed as a positive, if only because the diplomatic balance is tipped ab initio: Yaakov is presenting self-effacement before he can show strength.
[One wonders whether Shimon and Levi’s ostensible”overreaction” after Dina’s rape and the surreptitious manner in which they subdue the entire populace—even given the ultimate justification for the action—is to preempt a possible overture that might be deemed too diplomatic, which might be borne out by the exchange with Yaakov at the end of the Chapter after Shechem is wiped out.]
Even Yaakov’s sending Yosef to look after his brothers in the middle of Chapter 37 after having himself referred to the hostilities between the brothers [a possible angle to interpret “shamar es hadavar”?] indicate a somewhat misplaced faith in diplomacy.
It might no be accidental that Yehuda learns his most crucial diplomatic lesson and where to draw lines from his erstwhile daughter-in-law Tamar, who has seduced him in response to his essentially rendering her an agunah despite the fact that his sons were at fault for their demise.
When Tamar forgoes the explicit naming-and-shaming even at the possible cost of her life using material evidence and coded language that only Yehuda could and would understands, she actually exemplifies the best of diplomatic traditions even more than a knee-jerk adherence to pre-Sinaitic notional of halbanah: knowing that both she has taken advantage of Yehuda’s blind spots and on the cusp of fulfilling a messianic mission, she invites him to now consent to the mission he’s been avoiding. What she DOES manage to by not making it personal is keeping said mission under wraps, even from him, until this very moment. Making it personal by embarrassing him might save her life but would cancel the mission for both of them, and somehow she’s seen enough to count on her triggering an epiphany of his part.
[In fact—at the risk of violating a certain level of moreh halacha lifnei rabbanim—anyone who uses Tamar as the paradigmatic example of avoiding embarrassing someone even at the cost of ones own life—STOP IT. There’s SO much more going on in the Yehuda-Tamar narrative; making the ostensible halbanah its sole locus and then generalizing it as a teachable moment for tinokos shel beis rabban ensures that understanding the maaseh never gets past that level. It’s frankly….embarrassing.]
The sum total of all these lessons—his and his forebears—were not lost on Yehuda in crunch time. And—like the texts that until now seems to scrutinize him more than the exegetes—this time, the textual narrative in Chapter 44 is very diplomatic/carrot, but the subtexts are very….stick. [“I’ll kill you and your master.”]
And while the instant effect looks perplexing—Yehuda didn’t know who he was talking to—the ultimate effect almost mirrors the midi kneged mida in reverse that Yehuda experienced when Tamar subtly called him out and he admitted that she had the mission correct: this time, Yosef assuages Yehuda, telling him that there was a mission to complete that he was unaware of, but that this time he did everything he was supposed to.
And finally, Yosef, by revealing himself and letting his brothers know that this stage of the mission has been completed and even giving them credit for helping bring about the completion—also tells them that, in way, this was all pre-game: the real contest hasn’t even begun yet.
Which is why it’s Yehuda who gets sent to Goshen to lay the groundwork.
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