The various commentators seem to have one theme in their understanding of hbceghu. Targum Onkelos interprets it as “he has outsmarted me.” Ibn Ezra relates this term to ceg, as in ckv ceg (crooked heart), thereby meaning “to take a crooked and cunning route.” Rashi explains it as “setting a trap.” They all seem to be consistent in explaining ceg as including the idea of devious undertaking with malice aforethought to reach one’s goal. Indeed, this analysis is confirmed by the fact that Yaakov was compelled to “trick” his brother on two occasions.
As Rabbi E. Munk z.t.l. notes, this definition seems to detract from that unique middah, trait, of emes, truth, which characterized the very essence of Yaakov. This middah is viewed by Chazal as the predominant quality of Yaakov’s personality and the ideal to be achieved in his life. Throughout his life, Yaakov, the epitome of honesty and integrity, had to struggle with such adversaries as Esov and Lavan. The latter are people who “exemplify” deceit, hypocrisy and guile. Later on in his personal family life, he is subjected to the infighting and untruths of his own children and the mockery of Shechem made by Shimon and Levi. Yaakov seems to carry the responsibility of settling conflicts wherever he goes. As Rabbi Munk notes, however, these painful trials offered Yaakov the opportunity to raise the virtue of truth to its highest perfection — through tenacious confrontation with those elements opposing it. In the end, the emes of Yaakov was victorious; the Patriarch emerged from his ordeal with greater eminence and dignity.
In a profound thesis, Rabbi Munk explains that the Torah is actually indicating that there are times when guile and cunning are essential defenses against the onslaught of Esov. Yaakov Avinu, who represents Am Yisrael, at times is compelled to resort to these unconventional methods against his rival Esov. Esov had no scruples in his battle against Yaakov. Yaakov, on the other hand, confronted an impossible situation. Thus, he was well within his rights when he responded in the manner he did. Whenever the struggle for survival against the forces of Esov becomes perilous, Yaakov’s descendants are to use whatever devious means available to escape this ruthless enemy.
This obliquitious recourse, however, can only be temporary in nature. Indeed, the name Yaakov, which alludes to this unbecoming approach, was changed by Hashem to Yisrael, which denotes royalty and nobility. This change indicates Yaakov’s accession to a higher level of achievement with respect to his holy mission of fighting for Hashem. The names Yaakov and Yisrael interchange frequently in the centuries of the epic struggle between the descendants of Yaakov and the descendants of Esov.
Only at the “end of days,” during Y’mos Ha’Moshiach, will a third name Yeshurun, Replace them. The name “Yeshurun” signifies staltwartness and uprightness (derived from yashar, straight). This name emphasizes that Jewry will finally have the strength and direction to follow a straight and unswerving path towards realizing their desired goal of service to Hashem.