The Parsha ends with an account of the genealogy of Esav. In the midst of this we are told of the birth of Amalek, the progenitor of the nation that would constantly strive to destroy Klal Yisroel. “And Timna was a concubine to Eliphaz and Eliphaz gave birth to Amalek..”
The Gemara in Sanhedrin informs us of the background to this terrible occurrence. “Timna was a Princess, but she wanted to convert. She came to Avraham, Yitzchak and Yaakov [to convert] but they would not accept her. She then became a concubine to Eliphaz the son of Esav. She said that it was better to be a maidservant to this nation rather than be a powerful woman in another nation. [As a result] Amalek, who would cause Yisroel great pain, was born from her.
What is the reason [that this incident produced Amalek]? Because they [the Avos] should not have distanced her.” Rashi explains that the Gemara means that they should have allowed her to convert.
It seems clear that the Avos had sufficient reason to reject Timna’s efforts to join their nation. They were aware of the evil within Timna’s nature.Consequently, they refused to allow her to join the Jewish people. Accordingly, why were they punished so harshly for their seemingly correct decision? Rav Chaim Shmuelevitz zt”l explains that we learn from here that no matter how bad a person is, one should not totally reject him.It seems that the explanation for this is that as long as there remains any hope that the person will improve their ways it is forbidden to distance them and thereby remove any chance of their doing teshuva. Evidently, there was enough hidden potential within Timna that justified allowing her to join Klal Yisroel.
Rav Shmuelevitz says that we learn a similar lesson with regards to Avraham Avinu’s relationship with his wayward nephew, Lot. Avraham only split up with Lot when machlokes threatened to sour their relationship. Rav Shmuelevitz points out that Avraham did not receive prophecy whilst Lot was with him due to Lot’s presence. Nonetheless, Avraham refrained from distancing Lot until he perceived that there was no hope of preventing Lot’s yerida.
Despite all of Avraham’s efforts and self-sacrifice in helping Lot, Chazal still criticize him for distancing his nephew. “Rav Yehuda says, there was anger against Avraham Avinu at the time that he separated his nephew from him; Hashem said, ‘He (Avraham) clings to everyone but to his own nephew he does not cling?!’” Even though Avraham made great efforts to influence Lot and was even prepared to lose the gift of prophecy in order to influence him, nonetheless he is criticized for eventually sending him away.
We have seen how it is incorrect to reject someone if there is any chance of saving him. What then is the correct approach to dealing with this difficult issue? The Ohr HaChaim HaKadosh sheds light on how to deal with a wayward child in his explanation of why Yitzchak wanted to bless Esav instead of Yaakov. He argues that Yitzchak was totally aware of Esav’s low spiritual level, and he nevertheless wanted to give him the Brachos. He writes; “The reason that Yitzchak wanted to bless Esav Harasha was that he believed that through receiving the blessings, he (Esav) would change for the good and improve his ways, because righteous people feel pain when their children do evil and he (Yitzchak) was trying to help him improve his ways. And it is possible that it would have worked.”
The Ohr HaChaim does not explain how giving Esav the blessings would have caused him to improve his ways. It is possible that giving the Brachos to Esav would give him great encouragement and show him that his father had faith in his ability to continue the legacy of the Avos. Such a show of confidence could in and of itself be the catalyst to causing Esav to change his ways. We learn from here that encouraging and showing faith in the wayward person is a key tool in helping him find faith in himself and giving him the strength to change his ways.
We see this principle with regard to a remarkable story involving Rav Yitzchak Hutner zt”l. There was a bachur in his yeshiva who was struggling badly with his learning. As a result he was severely lacking in self-confidence and found himself in a downward spiral that placed him in great danger of drifting away from observance. Rav Hutner was giving a Gemara shiur and this Bachur asked a seemingly ordinary kasha.
On one occasion Rav Hutner responded as if he had asked a tremendous question and throughout the shiur repeated it several times with great admiration. Receiving such adulation from a Gadol gave a tremendous boost of self-confidence to the boy. As a result, after this one occasion he stemmed his yerida and experienced an incredible turnaround in his confidence, learning and general observance. His relatives described Rav Hutner’s achievement as no less than ‘techias hameisim’(reviving of the dead). By showing this young man that he was able to learn, Rav Hutner was able to give him the boost that saved his Yiddishkeit.
We learn from the incident with Timna that rejecting a person as a hopeless cause is a very serious matter. If Chazal tell us that Timna, the person who produced Amalek, was deserving of a chance to join Klal Yisroel, all the more so, a person who is struggling with his Yiddishkeit, deserves the opportunity to improve himself.
We also learn from the Ohr HaChaim’s explanation in Parshas Toldos that showing faith in a person is a tremendous way of helping him change his ways.
These principles do not only apply with regard to people drifting from Torah, they also apply to our general hanhagos with our children, students and people around us. The Gemara in Sotah tells us that we should push away with our left hand and bring in with our right. The right hand is stronger than the left, thus the Gemara is telling us that we should always give precedence to positive reinforcement over criticism. Showing others the inherent good in them is the most effective way of bringing about improvement.
May we all merit to bring out the best in ourselves and those around us.
Notes and sources
 Vayishlach, 36:12
 Sanhedrin, 99b.
 See Rif in Iyun Yaakov, Sanhedrin, 99b who offers a different explanation why the Avos rejected Timna. He explains that she was a mamzeres and they were concerned that if she joined the Jewish people nobody would want to marry her because of her tainted yichus.
 Sichos Mussar, Parshas Pinchar, Maamer 85. The one exception to this rule seems to be when the wayward person seriously threatens the spiritual well-being of those around him. This explains why Avraham banished Yishmael because Yishmael constituted a grave threat to Yitzchak Avinu. In a similar vein it is said in the name of the Chazon Ish that a bachur in Yeshiva is comparable to a sick person in hospital. Throwing a bachur out of Yeshiva is comparable to throwing a sick person out of hospital! The one exception he made was if the sick person’s disease is contagious and threatens the health of everyone else. So too, a wayward bachur should only be thrown out if his actions can seriously effect his fellow bachurim.
 Bereishis Rabbah, Ch.41:8.
 Ohr HaChaim, Toldos, 27:1.
From The Book “The Guiding Light 2”