'And Eisav saw that the daughters of Canaan were evil in the eyes of his father Yitzchak. So Eisav went to Yishmael and betrothed Machalas, who was the daughter of Yishmael, Avrohom's son, and who was the sister of Nevayos, as an additional wife.' (Bereshis 28:8-9)

Rashi (on pasuk 9) notes from Bereshis Rabbah that Machalas, Eisav's new wife, was an evil person, and that Eisav remained married to his earlier Canaanite wives after he betrothed Machalas, merely adding the wicked Machalas to his household. This prompts one to ask why the Torah implies that Eisav betrothed Machalas in order to please his father Yitzchak, who was opposed to Eisav's marriages to Canaanite women due to their evil ways. By marrying Machalas, Eisav took yet another evil wife (who was not from Canaan, but was nonetheless evil), and he retained his Canaanite wives as well! How could Eisav have imagined that marrying Machalas and staying married to his first wives would please his father?

Before we try to answer this question, we need to address an ever more perplexing matter. We read (27:36-39) that, upon discovering that he blessed Yaakov rather than Eisav, Yitzchak confirms that Yaakov would keep the berachos he received and states to Eisav that the berachos bestowed upon Yaakov are irrevocable. Yitzchak thereupon grants Eisav an inferior set of berachos and verifies that Yaakov will be the dominant progeny. After this experience, one would expect Eisav to resent his father, who seemed quite at peace for having blessed Yaakov with the berachos reserved for Eisav and showed no anger toward Yaakov for what he did. Why – after this episode of the berachos - did Eisav still seek to please his father?

Rav Moshe Chaim Luzatto in Mesilas Yesharim devotes much discussion to one's awareness of his actions and his general path in life. The Jew is required to constantly review his deeds and his direction, never having the attitude that he can ‘take it easy’ and assume that he is set on the correct path, needing no correction or redirection. On the contrary, the Jew must systematically reevaluate his actions and direction in light of what the Torah requires and expects, and he must be prepared to make all changes necessary to keep on target. Those who fail to do so and are set in their ways are bound to falter. The Mesilas Yesharim (ch. 5) notes that the truly wicked do not change as a result of introspection or exhortations; only punishments from Hashem can possibly cause the truly wicked to rethink their ways. The righteous, who are humble, are never over-confident and routinely question their actions, correcting them without being pressured to do so; the resha'im, in their haughtiness, do not doubt their ways and often only change them under duress.

In light of this, we can understand what Eisav was thinking. Unlike a righteous or average individual who would have 'gotten the message' and perceived that the reason that he was denied something in favor of another person was very possibly because of that person’s superior merit in the eyes of Hashem, Eisav’s wickedness did not allow for such reflection. Eisav could not imagine that he did not earn Yitzchak’s berachos as a result of his evil ways; the idea did not cross his mind. Rather, Yaakov was to blame for scheming to steal the berachos, reasoned Eisav, and Yitzchak had now himself become a victim of Yaakov, as was he (Eisav). Eisav understood that the berachos were irreversible, and he viewed Yitzchak as having come to terms with Yaakov’s usurping of the berachos which rightfully should have gone to Eisav, but went to Yaakov instead, with Yitzchak’s regret but acquiescence.

Eisav’s evil character prevented him from engaging in introspection and viewing the situation objectively; he could only construe it in a way that did not bring his own merit into question. As a result of his subjective interpretation of what transpired, Eisav had no reason to resent his father, for Eisav viewed himself and Yitzchak as co-victims of Yaakov, the only one whom Eisav could contemplate as evil. The idea that Hashem had determined that Yaakov was more deserving of the berachos and that He therefore caused Yaakov to receive them did not cross Eisav's mind.

We can now understand Eisav’s actions pertaining to his new wife, Machalas. Eisav did not entertain the idea that he needed to change – that his original choices of spouses were objectively wrong and needed to be corrected. Eisav did not feel that the negativity associated with his first wives imputed any wrongdoing to him. On the contrary, Eisav was of the opinion that his first wives were objectionable because of their ancestry, for they stemmed from the base nation of Canaan; he blocked out the possibility and allegation that there was anything inherently wrong, at least not in a way that related to him. Therefore, rather than eradicate the evil from his household and disassociate himself from the wicked, Eisav took a spouse who was of the best lineage, thereby easily solving the problem, as he viewed it. Eisav did not question his path or assess the true correctness of his actions; he interpreted the situation in a myopic, pragmatic and narrow manner, refusing to engage in introspection or to really face himself and evaluate how he was leading his life. Just as he concluded that he ‘lost out on’ Yitzchak’s berachos due to the sneakiness of Yaakov and did not think of the possibility that he (Eisav) was denied the berachos because he was not worthy of them, Eisav viewed the problem with his wives as a superficial and technical matter that could be easily solved by merely adding a woman with good lineage to his home, overlooking the underlying problem. Having readily and satisfactorily resolved the issue of his wives, as far as he was concerned, Eisav expected his father to be quite pleased.

There is a contemporary term used for those who think on a broad, creative and often unconventional scale: ‘thinking out of the box’. This cliché (which will likely be overused and forgotten in the near future) encapsulates how the Jew must live. The Jew is not permitted to be ‘set in his ways’ as regards his actions, lifestyle and values. He must honestly assess his path and deeds with utmost objectivity and determine if or when change is needed, and he must be prepared to make such change, no matter how creative or radical, if his path and deeds are not in conformity with what is expected. The measuring tool for the Jew’s self-assessment is the Torah, and the Jew’s life must be calibrated to conform to it. Eisav refused to look into himself and audit his soul. Yaakov and his household, whose examples we are bound to follow, demonstrated how to evaluate one’s self and correct one’s path – no matter what it takes – to affect true personal change and betterment.