ויאהב יצחק את עשו כי ציד בפיו ורבקה אהבת את יעקב
Rashi explains tzayid b’fiv as “cunning in his mouth.” Eisav was extremely smooth and able to articulate halachic questions, thereby giving the ruse that he was meticulous in his observance – which he was not. The obvious question is: How did Eisav pull one over Yitzchak Avinu? To suggest that, due to his immense level of kedushah, our Patriarch was slightly “naïve” in the evil ways of the world demeans the greatness of Yitzchak. Being holy does not mean being naïve. Indeed, Torah study makes one wiser and equips him with greater acuity. We have no question that Yitzchak knew…
