"Yisshaq loved Esav, because ‘sayid’ in his mouth, but Rebekah loved Yaacob." (Toledot 25:28)
In Hebrew the word means to hunt and the noun form of the word means wild game (the animal hunted). In this week's parasha, we learn that Yisshaq favored Esav because there was "sayid in his mouth". This verse is ambiguous, for we do not know whose mouth the verse is referring to. Rashi gives two different explanations for this verse, and we will investigate why.
First, Rashi states that the simpler meaning of the verse is that the mouth is referring to Yisshaq's mouth, as the Targum translates. The verse is telling us that Yisshaq favored Esav because he always brought wild game to feed his father Yisshaq. And so, because of this ‘sayid’ that was always in Yisshaq's mouth, Yisshaq favored Esav over Yaacob.
Second, Rashi states the opposite. The mouth in the verse is referring to Esav's mouth, and the ‘sayid’ is referring to Yisshaq himself! Esav used to deceive or entrap his father by asking questions in the nounces in halacha, trapping Yisshaq (the hunted) with his questions. Yisshaq was led to believe that Esav was a God-fearing person, and consequentially favored him more than Yaacob.
Why does Rashi give two different answers?
When Rashi gives two different answers, we must discover the problem in the first that the second answer fixes, and the reason why the first answer was still provided first, despite any lacking there might be in its solution. When Rashi explained that "his mouth" refers to Yisshaq's mouth it is difficult. For the word "his" would naturally go back to the last person mentioned in the verse, namingly Esav. In addition, there is no verb to describe that Esav "put" this food or "gave" this food to Yisshaq. Yet still, this answer does stick to the natural definition of "sayid" to mean wild game.
In the second answer, Rashi brings the midrash which tells how Esav entrapped Yisshaq with words. Here, the term "his mouth" does go back to the last person in the verse, and there is no need for a word to portray something being given over, because here Yisshaq was the actual item being hunted. In the second solution, both of the above mentioned problems are solved. However, the lack in this solution is that we turn away from the simpler meaning of ‘sayid’ and instead interpret it to mean "words that are entrapping."
The complexities one can find in Rashi, and the subtleties in his answers, are as vast as the ocean.