As Jacob's family gets ready to meet Esau, Jacob arranges them in backward priority - maidservants first then Leah then Rachel. So that if, G-d forbid, Esau attacks them, then the most beloved will be spared because they will be further back in line. Then the Torah says:
He placed the maidservants and their children first, Leah and her children later (in Hebrew 'acharonim') and Rachel and Joseph last ('acharonim.')
And Leah and her children later (acharonim').: Rashi: The most last is the most beloved.
This is a famous Rashi quote. In Hebrew it is 'Acharon, acharon, chaviv."
But this comment is puzzling. It seems to say that Leah is the most beloved, whereas we know that Rachel was Jacob's most beloved wife. Why then does Rashi say, in reference to Leah, 'the most last is the most beloved'? And if you will say that the most last in this line is Rachel and thus she is the most beloved, then I ask why does Rashi make his comment on the words "And Leah and her children later"? He should have made it on the words "And Rachel and Joseph last."
An Answer: It is true that the most last is the most beloved. It is also true that Rachel was the most last. It is also true that she was the most beloved to Jacob.
And while all this is true, nevertheless Rashi did not make his comment about Rachel. The reason is that Rashi was bothered by something in this verse. Can you see what that is?
What Is Bothering Rashi?
An Answer: Rashi is bothered by the word "acharonim" after Leah's name. Leah was not last, why then does the Torah say that Leah and her children were 'acharonim'?
Rashi's answer is that the word 'acharonim' does not necessarily mean 'last,' it can also mean 'latter'. It is a relative term. Leah was 'last' vis a vis the maidservants who came before her. On the other hand, she was not 'last' vis a vis Rachel who came after her. And the reason Rashi comments only on Leah, and not on Rachel where the same word 'acharonim' appears, is because the word 'acharonim' is apparently problematic when placed in reference to her, since she wasn't last. But when the Torah says that Rachel and Joseph were 'acharonim' last, that presents no problem, because in fact they were the last in line.
An Important Lesson
It is important to take notice of this. Rashi, in his commentary, never makes a comment just in order to teach us some wisdom, however true it may be (like the saying 'acharon, acharon, chaviv'). He comments only when there is something apparently problematic in the Torahs' words. Then he may use a wise saying to explain away the problem, as he does in our verse.
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