When we read the story of the sale of Esav’s birthright we see a sequence of events that seem at first glance to be completely out of order.
First, we see Esav selling his birthright to Jacob, then he eats and drinks, and finally, we are told that Esav disparaged his birthright.
Now for him to sell his birthright for a bowl of lentils and a drink wouldn’t it make more sense that he first trivialized its value and then gave it up for almost nothing, shouldn’t his contempt for it be expressed first as the reason he sold it?
Why is it that only after he sold his firstborn rights and responsibilities and satisfied his hunger that he then denigrates its worth?
The Torah, here, is describing, in very real terms, a very common human failing. When a person does or says something wrong in a moment of weakness, he later has feelings of regret or remorse. To subdue those feelings of guilt, instead of admitting his failure, he tries to justify his behavior by arguing that there was nothing improper with what he did and his actions were correct, thereby reinforcing his mistakes by denying that they were wrong in the first place.
One of our greatest prophets, Yirmiyahu, declared, “Your guilt will be for saying ‘I have not sinned.’” In modern terms, the coverup is sometimes worse than the crime! And why is this so bad? Because as we all know, when a person acknowledges his flaws, then there is hope that he can correct them (that is why it is the first step in the famous 12 step addiction programs). However, if he defensively rationalizes and justifies his behavior, there is no hope that he will correct them.
In the end, as the Torah states, Esav did not sell his birthright because he disparaged it, he disparaged it because he sold it.