There are two aspects of a person’s self-perfection: One is to excel in those traits for which he has a natural affinity; the other is to succeed in those areas that do not come naturally to him. The purpose of this second challenge is to demonstrate that one’s deeds emanate not from natural tendencies or habit, but from a pure desire to perform HaShem’s will, even when it contradicts his nature.
Yaakov Avinu is known the pillar of emes, truth, as it states in the book of Michah, “Give truth to Yaakov….” We see this quality of Yaakov’s in parashas Vayeitze. Accused of stealing Lavan’s idols, Yaakov responds by outlining his outstanding integrity: He never ate from Lavan’s flock, and if a sheep suffered an injury that reduced its value, Yaakov would deduct the loss from his own wages. Given Yaakov’s devotion to truth, it makes sense that he was tested in just this area.
Indeed, several major incidents in Yaakov’s life called for him to be less than honest. The purpose of such tests was to see if he could overcome his overriding devotion to truth when commanded to do so, or when it was clear that this was HaShem’s will.
The first and most famous of these tests involved deceiving Yitzchak Avinu in order to receive the coveted blessing he planned to bestow on the evil Esav. Rivkah overheard Yitzchak instructing Esav to bring him food, and then he would bless his son. Rivkah knew through prophecy that Esav did not deserve the blessings and that his receiving them would have tragic consequences. Accordingly, she instructed her pure son, Yaakov, to dress up as Esav, trick Yitzchak, and thereby secure the blessings. Yaakov was shocked at this directive and feared being exposed as liar. Nevertheless, Rivkah commanded him to comply, invoking his responsibility to listen to his mother. This way, Yaakov was convinced that it was G-d’s will that he deceive his own father in a matter of grave significance. Rav Yaakov Kamenetsky, ztz”l, describes this challenge as Yaakov’s own “Akeidah,” as difficult for Yaakov as the binding of Yitzchak was for Avraham.
Many years later, Yaakov returned to Eretz Yisrael, facing a hostile Esav. Yaakov appeased him so successfully that Esav offered to travel with him. Yaakov declined, promising to rejoin his brother at Mount Seir. In truth, Yaakov had no intention of catching up with Esav, and therefore he was technically lying. Under the circumstances, however, it was clearly correct to deceive Esav. Any other approach would have been disastrous for Yaakov’s family.
A final example of Yaakov’s bending the truth is the incident with Shechem. After Shechem had abducted Yaakov’s daughter Deenah, Shechem’s father, Chamor, king of the Chivim, suggested that the two of them marry and that the two nations join together. Rav Kamenetsky explains that Yaakov and his sons planned to trick the Chivim into circumcising themselves, and then the brothers would rescue Deenah. Yaakov realized it was impossible to be honest with people like Shechem and Chamor. However, without Yaakov’s knowledge, Shimon and Levi killed all the men in the city.
We have seen how Yaakov Avinu’s most difficult tests forced him to act in conflict with emes, verifying that Yaakov was capable of defying his truthful nature when that was HaShem’s will. In addition to the general principle that one must perfect the character traits that go against his nature, we learn a vital lesson in our approach to truth from Yaakov Avinu. A person may believe that emes overrides all other considerations, even when the truth hurts. The Gemara lists a number of situations in which it is correct to speak untruthfully – for example, for the sake of modesty, humility, or helping others. Even HaShem deviates slightly from the truth to keep the peace between Avraham Avinu and Sarah Imeinu. These cases teach us that we must emulate Yaakov Avinu and realize that sometimes honesty is not the best policy.
Needless to say, one must be very careful not to justify falsehood for the wrong reasons. It is advisable to consult a Torah scholar whenever questions arise.
Another pertinent point with regard to lying l’shem Shamayim (for the sake of Heaven) derives from Yaakov’s attitude in such situations. When Yaakov expresses his reservations about lying to Yitzchak, he says, “perhaps (ulai) my father will feel me, and I shall be a mocker in his eyes.” The commentaries point out that two Hebrew words mean “perhaps” – pen and ulai. Pen always indicates a negative consequence, while ulai refers to a positive one. Therefore, Yaakov should have used the word pen. Deep down, however, Yaakov hoped he would be caught, despite the disastrous consequences. Such was his love of truth. We learn from here that even when a person must lie, he should feel repulsion at having to do so; if he enjoys it, his intentions probably are not pure.
May we all emulate Yaakov Avinu’s devotion to truth.
Notes and Sources
 Michah 7:20.
 Divrei Yirmeyah, quoted in The Stone Edition Chumash (ArtScroll Mesorah Publications), p. 135.
 Rav Yaakov Kamenetsky, Emes l’Yaakov, Bereishis 27:12
 See Rashi, Bereishis 33:14, who explains how Yaakov’s words were ultimately truthful, as they will be fulfilled when the Jewish people judges the nation of Esav on Mount Seir.
 Emes l’Yaakov, Bereishis 34:13.
From the book “Beacons of Light”