Parashat Toledot is a transitional one, in which the primary focus of the Chumash switches between the second and third of the Avot, from Yitzchak to Yaakov. For the next three Parashiyot, until the central drama shifts to the interactions between Yosef and his brothers, Yaakov Avinu represents the critical figure in the text.
Chazal, as we know, have associated Yaakov with the characteristic of Emet, truth, “Titein Emet LeYaakov,” just as his father is associated with Gevurah, courage, and his grandfather with the virtue of Chesed, kindness. Ab initio, the association seems strange. After all, the central incident of our Sidrah is one in which Yaakov, much to his own discomfort, deceives his own father. As Yitzchak himself notes to a crestfallen Esav, “Ba Achicha BeMirmah VaYikach Birchatecha,” “Your brother came in deception and took your blessing.” Even if Yaakov was not the one to initiate this decision, even if he was uncomfortable with it, and even if it was, in a sense, Kibud Eim, respect for his mother, his sheer willingness to engage in this kind of activity would seem to, in and of itself, disqualify him from association with the virtue of Emet.
Moving beyond this incident alone, Yaakov’s wresting of the Bechorah, birthright, from his brother by exploiting his fatigue and hunger, as well as his handling of the division of the sheep with Lavan and his brothers-in-law in Parashat VaYeitzei, would hardly seem to be the actions of the archetype of truthfulness.
In fairness, one may certainly justify our Sages’ association of truthfulness with Yaakov if one is willing to adopt a limited view which maintains that this association is rooted in the standards Yaakov maintained as an employee in the House of Lavan. As Yaakov himself testifies to his own wives, the daughters of his employers, “VaAteinah Yedaten Ki BeChol Cochi Avadeti Et Avichen,” “You know that I worked for your father with all my might.” To be sure, this aspect of Yaakov’s integrity and rectitude is on full display in the coda of Rambam’s Hilchot Sechirut, in which Yaakov’s honesty as an employee over two decades establishes the gold standard for the conduct of a hired laborer and earns Yaakov the prestigious appellation of Yaakov HaTzaddik.
This impressive feature of Yaakov’s personal integrity notwithstanding, one still yearns for a more holistic perspective on Chazal’s identification of Yaakov’s defining attribute as Emet. Perhaps we might suggest that Yaakov’s embodiment of the virtue of truth may indeed be best understood as a lifelong process of spiritual development, an evolution in his inner world.
In Parashat Toledot, Yaakov flees from his brother Eisav, much as in Parashat VaYeitzei, Yaakov flees from his father-in-law, Lavan, rather than directly and honestly confronting his erstwhile adversaries. As the Torah itself testifies, the latter was a clear example of deception, “VaYignov Yaakov Et Leiv Lavan HaArami Al Beli Higid Lo Ki Vorei’ach Hu,” “Yaakov deceived (lit. ‘stole the heart of’) Lavan the Arami by not telling him he was fleeing.”
Parashat VaYishlach represents the critical turning point. As Yaakov prepares for his confrontation with Eisav, he is all alone. He must stand and struggle with the man-angel. In this confrontation, Yaakov loses his capacity to run, as his leg is injured. However, he has gained something far more important: the confidence that he need not run from his problems nor engage in any other form of machination, but that he can confront his adversaries honestly and directly. As we know, Yaakov’s identity is transformed at this point to Yisrael, representing a transition from “VaYa’akeveini Zeh Pa’amayim,” He has deceived me twice,” to Yashrut, honesty and integrity. And even as he is wounded in the physical sense of the term and may no longer match the descriptive term of his youth, Tam, perfect, he is now, ironically, even with his Mum, blemish, so to speak, elevated to Sheleimut, completeness.
From this point forward, Yaakov’s life is marked inexorably by an unwavering commitment to direct and honest dealings even with the most difficult situations. When he meets Eisav in the next chapter, he asks Eisav to take back the blessing he has gotten through deception, “Kach Na Et Birchati Asher Huvat Lach Ki Chanani Elokim VeChi Yesh Li Chol,” “Please take my blessing that was brought to you, for God has favored me and I have everything.”
Critically, Yaakov does not run from Esav, but on the contrary, he confronts him directly, as the Pasuk says, “VeHu Avar Lifneihem,” Yaakov goes directly to the front of his carefully choreographed encampment. 
Likewise, in the difficult trials resulting from Dinah’s abduction in Shechem, Yaakov excoriates his sons for engaging in Mirmah, deceptive plotting. While the simple reading of the Torah indicates that Yaakov was primarily concerned about the practical implications of his sons’ violence, “VeNe’esfu Alai VeHiCuni VeNishmadti Ani UVeiti,” “They will gather upon me and kill me, and I and my family will be destroyed,” the end of Sefer BeReishit tells a different story altogether. As we know, Yaakov never truly forgives Shimon and Levi for their violent plot, continuing to reference their deception even on his deathbed, “Shimon VeLevi Achim, Kelei Chamas Mecheiroteihem. BeSodam Al Tavo Nafshi, BiK’halam Al Teichad Kevodi,” “Shimon and Levi are brothers; their weapons are tools of lawlessness. Let my soul not enter their council; let my honor not be included in their assembly.”
It seems to me that Yaakov’s lifelong growth, in which he cultivates over time a unique sensitivity and capacity for expressing direct truthfulness, even in difficult situations, may also play a role in what might be otherwise perceived as one of the great errors of Yaakov’s life: sending Yosef alone to the dangerous area of Shechem, to the brothers Yaakov well knows are, to put it mildly, in friction with Yosef. Perhaps, though, Yaakov’s decision to send Yosef was motivated by a desire for Yosef to be able to work out the growing tension that he was experiencing with his brothers in an honest and direct manner. Tragically, things do not work out as Yaakov might have hoped. But a man who spent his life developing the quality of truthfulness may not have had it any other way.
If we are to accept this approach to the affiliation between Yaakov and truthfulness, a related point comes into, I believe, a completely new light. In the prophetic final Pasuk of the Navi Michah, which serves as the basis for the association between Yaakov and truthfulness, his grandfather, Avraham, is associated with Chesed.
There is no doubt whatsoever that this description can be justified, whether it is our first Patriarch’s adoption of his nephew and subsequent risk of his own life to rescue him from bondage; his astonishing capacity for welcoming guests in a state of postoperative infirmity; or his intercedence with the Almighty on behalf of the people of Sodom. And yet, when one contemplates Avraham’s early life through the prism of various Midrashim, and especially in Rambam’s classical description in the first chapter of Hilchot Avodah Zarah, the iconoclastic quality of Avraham’s youth comes to the fore. In his youth, apparently, Avraham brought his Keri’ah BeSheim Hashem, monotheistic message, to a pagan society through the means of confrontation and iconoclasm; he literally and figuratively Shibeir Et HaTzelamim, smashed the idols. Far from leaving an impact on the society around him, Avraham escapes with his own life only through a miracle. Neither Nimrod, nor the denizens of Ur Kasdim for that matter, are elevated through this process.
Moving from the realm of the Midrash to the text, one notes a striking instance of selfishness on the part of Avraham. When Avraham expresses concern for his own life as he descends to Egypt together with Sarah, he asks her to expose herself to enormous risk for his sake. Whether or not it would have been appropriate for Avraham to expose Sarah to Pharaoh merely to save his own life is itself debatable, though the Ramban was unequivocal that even self-preservation could not possibly have justified exposing Sarah to this situation. What seems to me beyond debate is the acceptability of doing so for material benefit, which Avraham articulated as his first, and perhaps, primary motive, “Lema’an Yitav Li Ba’avureich, VeChayetah Nafshi Biglaleich,” “So it will be good for me because of you, and I will survive because of you.”
And yet, as he develops, Avraham dramatically alters his approach. He is still, of course, Korei BeSheim Hashem, calling out in the name of Hashem, but as Chazal describe so vividly, he does so not through confrontation but through compassionate engagement, the Achilah Shetiyah ULevayah, eating, drinking, and accompaniment of his Eishel, to the point where he becomes the paragon of “SheYihyeh Sheim Shamayim Mit’aheiv Al Yadecha,” “the name of Heaven should be loved by you.” The results are self-evident; it is not for naught that the Hittite denizens of Kiryat Arba refer to Avraham as the “Nesi Elokim,” “prince of God.”
In this respect, then, a new parallelism between Emet LeYaakov and Chesed LeAvraham emerges: both are authentic descriptions of a life’s work of molding of one’s inner world, in which each of these respective Avot reversed a certain spiritually suboptimal proclivity of their youth into the defining quality of the unstinting Avodat Hashem of their mature years. In the timeless words of Rabbeinu Yonah, “HaSeichel Matanah VeHaMusar Kinyan,” “Intellect is a gift, but character is acquired.”
 See, for example, BeReishit Rabbah 70:7.
 The prophetic root of this association can be found in Michah 7:20. In context, the reference to Yaakov is not a reflection on his personal honesty but rather a petition to the Almighty to fulfill the promise he made to Yaakov, as noted by Rashi, Ibn Ezra, Radak, and Metzudat David ad loc.
 BeReishit 27:35. Admittedly, Onkelos and Rashi both take the edge off the term and simply render it “BeChochmah,” “with wisdom.” Yet, it should not be lost on us that “BeMirmah” is precisely the term the Torah uses to describe the deception perpetrated by Yaaakov’s sons (discussed below) on the people of Shechem, which so infuriated Yaakov. Moreover, this is precisely the term Rambam (discussed below) chose in Hilkhot Sekhirut as a contrast with the honesty of Yaakov as an employee of Lavan.
 BeReishit 31:6
 Rambam Mishneh Torah Hilchot Sechirut 13:7
 BeReishit 31:20
 BeReishit 27:36
 Admittedly, Chazal do assert that Sheleimut reflects the healing of his wound and therefore is not mutually exclusive with a state of physical Temimut, perfection. See Rashi to 33:18. In contrasting the two, I have opted to follow the simple Peshat of the text, which does not indicate that Yaakov healed from his confrontation with the man-angel.
 BeReishit 33:11
 BeReishit 33:3
 BeReishit 34:30
 The shift in Yaakov’s rationale for being critical of Shimon and Levi from a pragmatic concern to a more fundamental one concerning the use of such deceptive violence seems critical to me in illuminating another element of the text. When Yaakov voices his concerns in practical terms in Chapter 34, the Torah quite famously cedes the last words in the discussion to Shimon and Levi, “HaCheZonah Ya’aseh Et Achoteinu?” “Shall he make our sister like a harlot?” Yet, when Yaakov gives voice to a deeper, more principled objection to his sons’ behavior at the very end of his life, the Torah very clearly gives him the last words on the incident.
 BeReishit 49:5
 Ramban to BeReishit 12:10, s.v. VaYehi Ra’av BaAretz.
 BeReishit 12:13. See Rashi, ad loc., who explicitly notes that Avraham was interested in the gifts that he thought he would receive as Sarah’s brother. In fairness, see Radak, ad loc., who is scandalized by Rashi’s approach.
 Sotah 10b
 Rambam Sefer HaMitzvot Asei 3
 BeReishit 23:6
 See commentary of Rabbeinu Yonah to Avot 5:12.