Both Yitzchak and Rivka were aware that Esav was not the perfect son. We see this in Parshat Toldot, Breisheet 26:34-35: “Esav was forty years old when he married Yehudit, the daughter of Be’eri the Chitite and Bosmat the daughter of Eylon the Chitite. They were a source of spiritual bitterness to Yitzchak and Rivka.”

What was so bad about these wives that caused Yitzchak and Rivka so much distress?

The Chitim were one of the seven nations that the forefathers specifically asked their children not to marry.

Breisheet Raba 65:4 explains that these women were idol worshippers.

Radak states that Esav specifically married these women in order to aggravate his parents.

If that is the case, then why did Yitzchak want to bless Esav?

Both Radak and Or HaChayim believe that Yitzchak did in fact see Esav’s faults, yet he was hoping that giving Esav a blessing may help improve his behavior.

Did Yitzchak’s blessing help influence Esav to become a better person?

We do see Esav making a slight effort to please his parents in Chapter 28:8-9: “Esav realized that the daughters of Cnaan were evil in the eyes of his father. Esav then went to Yishmael and took Mochlat the daughter of Yishmael, the son of Avraham and sister of Nevayot in addition to his other wives for a wife.”

It looks from here that Esav did take notice that Yitzchak told Yaakov not to marry the Cananite women.

According to Chizkuni, Esav thought that the reason that his father did not bless him with the inheritance of the Land of Israel was because he married the Cananite wives. Esav was hoping that if he would marry Yishmael’s daughter then maybe he would be worthy of inheriting the Land of Israel.

Marrying Yishmael’s daughter was a step up from marrying the Canaanite wives yet he remained married to his first wives as it says “in addition to his other wives”. Rashi points out that Esav did not divorce his first wives.

It is hard to imagine that a child who strayed off of the path will come back. However we must continue to bless all of our children.

Even Esav who seemed so far gone still said to his father in 27:32: “Bless me too, my father.”

In the end, Esav did not inherit the Land of Israel. However he did receive the blessing in 27:40: “…When you have cause to be grieved, you will throw off your brother’s yoke from your neck.”

According to Rashi, if the Israelites transgress the Torah and are undeserving of dominion, then Esav will have a right to be aggrieved that Yaakov has taken the blessing and then Esav may cast off Yaakov’s yolk from his neck. This is the fulfillment of Rivka’s prophecy from when she was expecting the twins: the two sons would not be able to coexist, when one ascended, the other would decline.

Yitzchak’s blessing for Esav was fulfilled. The Romans are descendents of Esav and there are countless times in history that they ruled over the Jewish people.

We learn from here that we can never give our children too many blessings and there is no reason to exclude any of our children from being blessed.