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In Parashat Toldot, there seems to be a handful of deception schemes carried out by our forefathers, Yitzchak and Yaakov, and by our foremother, Rivka. One would expect - if we relate to the Torah as a guideline for moral conduct - that these acts would not go unpunished by Hashem. Yet, at first glance, it appears that not only is there no punishment for these actions; on the contrary, these immoral acts bring about blessing and good fortune to their perpetrators.

Yitzchak lies to the Plishtim about Rivka – falsely presenting her as his sister – yet still receives protection from their ruler, Avimelech, and prospers for some time in Philistine. Yaakov tricks both his brother, Esav, and his father, Yitzchak, and steals his brother's firstborn-blessing – yet faces no significant consequences, neither from his father nor from Hashem. Esav, on the other hand, a hard-working hunter, who respects his father and tells the truth, receives a token blessing, which is really a curse (see Bereishit 27:39-40).

How do the Torah and its interpreters reconcile this unfolding of events, where deception seems to pay and honesty fail?  
The medieval commentator, Rashi, tries to  soften the impact of Yaakov’s blatant lie – when Yaakov says "I am Esav, your first-born son" – Rashi suggests that what Yaakov really answered when Yitzchak asked him about his identity was, "It is I, comma –  Esav is your first-born son." Rabbi Shlomo Riskin, a prominent modern Orthodox rabbi in Israel, criticizes Rashi’s classical commentary for its forced and superficial attempt to reconcile Yaakov’s lie with the moral character we attribute to him and with his promising legacy.

It may be tempting to zoom in on the unfolding of events – Yaakov’s lie and the undeserved blessing that follows – and to conclude directly that before us is a clear case of unfairness and injustice, evidence of evil in the world, “Tzadik ve’Ra Lo, Rasha ve’Tov Lo” (it is the righteous who suffers and the wicked who prospers). But, if we zoom out and read further in the Parsha and in future Parashot, we see that Yaakov didn’t have it so easy after all.

Yaakov’s deception forces him to escape from his parents to his uncle, Lavan the Aramean. Later on, Lavan deceives him, giving him his eldest daughter, Leah, for a wife instead of Rachel. Yaakov then has to put in an additional 7 years to gain Lavan’s consent for marrying Rachel.

Several weeks from now, in Parshat VaYeshev, Yaakov’s sons also lie to him about his son Yosef. Yaakov is told that Yosef has fallen prey to a wild beast, when in fact the brothers have sold him to the Ishmaelites.

In reality, Yaakov took the easy route, and found short-term benefit (the blessing), but in the long run he had to pay, over and over again.  

What would have happened if Yaakov had confronted Esav and his father…if he had insisted on getting the blessing truthfully (which was well-deserved after he bought firstborn rights from Esav) as opposed to deceiving them and going behind their backs? We do not know – but it may have been the just, though definitely not the easy, thing to do at the time. In retrospect, Yaakov’s heritage, the heritage of the Jewish people, does not turn out all that rosy despite Yitzchak’s blessing - slavery in Egypt, 40 years of roaming the desert, the destruction of two Temples and living under exile and persecution for most of Jewish history – by no means the manifestation of a perfect blessing.

Notwithstanding, Yaakov only starts to see this blessing come alive after struggling all night with the angel of Hashem in several Torah portions from now, Parshat Va’yishlach.  By morning, his name is changed to “Israel” – literally meaning to struggle with Hashem. Yaakov, in other words only becomes deserving of his heritage (albeit an imperfect one) after he has matured and transformed, after he has learned to stand up for himself, and, better yet, to tell the truth. I don’t think it is a coincidence that the word “ישראל” consists of the words ישר – אל , literally meaning “honest” and “God” or honesty before Hashem. We could interpret this to mean that sometimes telling the truth may not be easy, it may involve a struggle, but it is a struggle that will eventually be worth our while.

It is this kind of struggle that is part of the Jewish DNA. As the people of Israel, we traditionally wrestle with each other (as evident in Talmudic discourse) and with Hashem. We confront, disagree, question, challenge ourselves and each other, and while it may not yield immediate short-term benefit, I believe that it is essential for meaningful long-term success and prosperity.

I often tell students of Israel advocacy that to be effective advocates they have to grapple with Israel’s past, gain mastery of the facts, and then, as advocates for Israel – (ישר-אל), they are obliged to tell the truth. They should realize that there are parts in Jewish – and Israeli – history that are not impeccably moral. And they should understand that to the degree to which they are able to acknowledge Israel’s imperfections, is the degree to which they will be able to fairly and effectively advocate for Israel. Still, I do not hesitate to share with them my belief that - for the most part - to be pro-Israel is to have truth and justice on our side.

I want students to realize that it is not always easy to confront others or to stand up for the truth. But I believe that these Jewish values – tenacity and honesty – which are eternally engrained in our name (Israel) – are fundamental in ensuring the survival and prosperity of the Jewish people today and in days to come.