In the beginning of the Torah section of Toldot (Bereshit 25:27), we read, “And the lads grew up and Esav became a man who knows trapping, a man of the field; but Jacob was a wholesome man, abiding in tents.” Regarding these descriptions, Rashi comments that “a man who knows trapping” refers to Esav’s ability “to ensnare and to deceive his father,” whereas Jacob’s being “wholesome” means that “he is not expert” in Esav’s behavior, but, instead, “as is his heart, so is his mouth.” Rashi sums up, “One who is not sharp in deceiving is called wholesome.”
In contrast to the aforementioned description of Jacob, his actions, on the other hand, as reported in the Torah, would appear to deviate considerably from that of an individual “not sharp in deceiving”! In fact, throughout the Torah’s anecdotes concerning Jacob’s life and travels, we find Jacob to be rather astute in outsmarting, first, his brother Esav, and, later, his uncle Lavan in utilizing quite clever and, one may say, duplicitous methods! More puzzling is the fact that Jacob is depicted throughout Jewish literature as the paradigm of truth (see Micha 7:20 et al). How do Jacob’s seemingly duplicitous actions jibe with his depiction as representing truth?
The Rebbe of Lublin, as cited by Ma’ayana Shel Torah (Bereshit 25:27), helps to clarify the seeming inconsistencies in Jacob’s character and the depiction of Jacob as representing truth by analyzing the matter more acutely. He points out that, to successfully promote truth and goodness, one must be in control of his character traits fully, knowing when and how to use them properly, for, at times, one must make use of an otherwise negative trait for good purposes, as our Sages say, “Whoever becomes compassionate when cruelty is in place, in the end becomes cruel when compassion is in place” (Kohelet Rabba, chap. 7). It is not enough, then, to develop the trait of compassion; one must also learn to control this trait and use it appropriately. Therefore, Jacob is not only referred to as “wholesome” but as a “wholesome man”. He was a “man” able to control and master his wholesomeness, knowing when to exercise it and when to put it aside, in order not to be taken unfair advantage of, following in G-d’s ways, as King David (Tehillim 18:27) extols the actions of G-d saying “with the crooked you act perversely.” This is what Rashi alludes to when he says, “One who is not sharp in deceiving is called wholesome.” One who does not know at all how to deceive is called “wholesome”. Jacob, however, although usually distancing himself, in practice and in thought, from his brother’s ongoing pattern of deception and deceit, knew when he needed to “fight fire with fire”. He knew how not to take the trait of compassion and honesty to self-defeating lengths. He knew when the situation called for the opposite. He knew that being compassionate did not include allowing those who are evil and lack compassion to thrive. He knew that promoting truth did not just mean not to tell a lie even if it meant allowing truth as a whole to be vanquished. He knew that to promote the proper spreading of real truth, and not let true and wholesome beliefs passed down from his grandfather Abraham to his father Isaac to be snuffed out by his consistently dishonest, deceptive and immoral brother Esav, negative traits, that are otherwise normally to be shunned, need, sometimes, to be employed, with appropriate control. Jacob represented truth because Jacob knew what it really means to promote truth.
With the crooked, you must be vigilant, not to let them get the upper hand. Allowing them to succeed will allow evil and wrong to flourish and suppress good and right. We must learn from Jacob. We must generally act “wholesomely” with great compassion, caring and absolute honesty, but we must know when and how to suppress this nature when we deal with the Esav’s and Lavan’s of the world who do not know or care what “wholesomeness” is. Only so can we ensure that the world as a whole will be a wholesome one. Only so can good succeed and righteousness flourish.