Rebecca said, “Now my son [Jacob] listen to me and heed my instructions. Go to the sheep and take two choice young kid-goats. I will prepare them the way your father likes. You must then bring it to your father, so that he will eat and bless you before he dies.”
“But my brother Esau is hairy,” replied Jacob, “I am smooth skinned.”
The Midrash [Genesis Rabbah 65:15] makes a strange comment about this dialogue: when Jacob describes Esau as hairy, he uses the Hebrew term “ish sa’ir,” which has the connotation of “demonic,” as in the verse from Isaiah, [13:21] “And satyrs (se’irim) shall dance there.” When he describes himself as smooth, he uses the Hebrew word chalak, having the same sense as in the verse from Deuteronomy, [32:9] “For the chelek (portion) of G-d is His people” which suggests that he was completely at one with G-d, so to speak, a part of G-d.
The Midrash compares Esau and Jacob to two men, one possessing a thick head of hair and the other bald, who stood near a threshing floor. When the chaff flew into the locks of the former, it became entangled in his hair. But when it flew on the head of the bald man he passed his hand over his head and easily removed it. In other words, hairy Esau’s wild demonic desires made him susceptible to getting messed up in the chaff of life; he was not able to easily cleanse himself of his wrongdoings. However, Jacob was a simple and straight fellow and was therefore less prone to getting caught up with his problems and any mistakes he might make he could easily fix.
This Midrash seems to indicate that Jacob was reluctant to do what Rebecca suggested not only because he feared getting caught by Isaac, but because he saw the act as lowering himself to Esau’s level. He did not want to incorporate qualities in himself that would make him vulnerable to sin, or endanger his state of purity and surrender by adopting such an orientation that would generate an even greater struggle with the evil inclination. His point was: Why complicate life? Let’s keep it simple.
When Jacob posed as Esau and deceived his father he actually accepted the struggles with the evil inclination implicit in the Esau-like orientation. He realized that for the sake of G-d and a true relationship of love he had to take this risk. Only a person capable of sinning and overcome the urge can really serve G-d. Only a person who is able to violate a loving relationship can really fulfill it.