One of the most perplexing episodes in the whole Torah is that of how Yaakov tricked his father, Yitzchak in order to receive the blessing meant for Esav. There are numerous, famous questions on this story, but one question that is less commonly asked is why, in fact Yaakov needed this blessing. The Chikrei Levnotes that the blessing that was due to Esav was totally physical in nature, with promises of material abundance. This would seem to have suited Esav’s temperament as he was engulfed in the material world. In contrast, Yaakov was an ‘Ish tam, yoshev ohalim’ – a pure man who learned Torah. Why would he need such a gashmius blessing when all he craved was spirituality? In addition, it is evident that Yitzchak always planned to bless Yaakov with the blessing that he did indeed give him right at the end of the Parsha, which is far more spiritual in nature, and is a continuation of HaShem’s blessing to Avraham. Accordingly, why was it so important for Yaakov to receive Esav’s blessings of gashmius? Another strong question on this episode is why did HaShem arrange the course of events that the protagonists in the story had to act with so much ramaus (deceit)?
The Chikrei Lev explains Yitzchak’s intention in blessing Esav – Yitzchak surely realized that Yaakov was on a higher spiritual level than Esav, but he believed that Esav’s role was to physically provide for Yaakov so that Yaakov could focus on spiritual pursuits. This indeed was the nature of the highly successful relationship between Yaakov’s sons, Yissachar and Zevulun – Zevulun provided for Yissachar’s physical needs so that Yissachar could focus on his spiritual growth. Therefore, Yitzchak believed that Esav was most fitting to receive the blessings that were completely focused on material abundance, not spiritual blessing. Yitzchak’s error was that he believed that Esav could become a righteous person through elevating the physical world in order to provide for Yaakov. However, in truth, Esav had become so engrossed in the material world, that he had no connection to spirituality, rather he was immersed in all kinds of immoral behavior. The Chikrei Lev emphasizes that Yitzchak always planned on giving Yaakov the blessing that pertains to spirituality because he felt that Yaakov’s role was in the purely spiritual realm. However, Rivka recognized that now that Esav wasn’t fitting to fill the physical role that was required, Yaakov had to assume that role as well and he needed the blessing that accompanied it in order to give him the ability to succeed in this role.
Had Yaakov directly asked Yitzchak for a blessing, his father would only have given him the spiritual blessing, but not the one that he designated for Esav. Because of that, Rivka realized that it was necessary for Yaakov to act in a derech ramaus (trickery) and dress as Esav so that he would merit to get the blessing of gashmius as well. The question remains as to why did HaShem arrange events that the blessing would come about through ramaus, as this would seem that this lessens the value of the blessings?
The two people in this episode who had to act deceitfully were Rivka and Yaakov – Rivka instructed Yaakov to mislead his father, and Yaakov carried out the deceit. It seems that there are different reasons why Hashgacha determined that each one was forced to act in this way. With regard to Yaakov, the commentaries note that his outstanding natural Midda was that of Emes – truth – and yet, in this episode, and in other times of his life, he was forced to act in a way that was ostensibly contrary to Emes. This was not a co-incidence. Rav Yaakov Kamenetsky explains that all the Avos faced extremely difficult tests and that these challenges were particularly in areas that challenged their natural inclinations. Rav Kamenetsky notes that even though a person excels in his Avodas HaShem through his own natural trait, there is still the possibility that he is not purely acting from a desire to perform HaShem’s will, rather that he is simply acting according to his nature. In order to test him to ascertain the intentions behind his actions, it is necessary to place him in situations where he is required to act against his natural inclinations. If he still succeeds in doing HaShem’s will it demonstrates that he was acting purely for the sake of HaShem. Thus, all the Avos had to succeed in overcoming great nisyonos that contradicted their nature.
With regard to Yaakov Avinu, he was placed into a situation where he was convinced that it was G-d’s will that he should deceive his own father in a matter of grave significance. Rav Kamenetsky describes this challenge as Yaakov’s own ‘Akeidah’ showing that this test for Yaakov was comparable in difficulty and significance to that of Avraham.
It seems that the nature of Rivka’s test was different. She in fact had grown up in a home and society that was steeped in dishonesty. In this vein, the Midrash states: “…It says, ‘and Yitzchak was forty years of age when he took Rivka, daughter of Besuel the Arami, Padan Aram; the sister of Lavan the Arami.” [This comes to teach that] her father was a ramai (trickster), her brother was a ramai, and the people of her place were ramaim – and this righteous woman emerged from among them…”
Rivka was very well-versed in ramaus and her greatness was that she was unaffected by all the deceitful people around her, and became a Tzaddekes in all areas. Yet, the Chikrei Lev notes, the fact that she was so familiar with dishonesty, enabled her, firstly to recognize the dishonest nature of Esav and secondly, to be unafraid to act deceitfully when necessary. However, it appears that her test in this area was to take the midda that she had seen misused by so many people, and use it in the right way with pure motives. She succeeded in this test, with tremendous positive consequences.
We have seen how an essential aspect of the process of the creation of the Jewish nation was the rectification of normally negative character traits, to be used for the right reasons. This reminds us that all Middos, whether ostensibly ‘good’ traits’ or what we generally characterize as ‘bad’ character traits, must be directed to Avodas HaShem. That motivation alone is what determines the righteousness or otherwise of how we apply our natural traits.
 Maamar 23.
 See Darash Moshe, ibid for a similar explanation.
 Such as his dealings with Lavan.
 Avraham had to act against his natural trait of Chessed in a number of his tests, in particular the Akeidah. Yitzchak’s test is a little less obvious, but Rav Dessler writes that it was to overcome his natural internal focus and fear of sin, and come out into the world to teach them about HaShem. (Michtav M’Eliyahu, Chelek 2, pp.`162-163).
 Emes LeYaakov, Bereishis, 27:12.
 Shir HaShirim Rabbah, 2:5.