Parshas Vayishlach

In arranging his family for the potentially explosive meeting with Esav, Yaakov placed the shfachos (Bilhah and Zilpah, the maidservant wives) and their children first, followed by Leah and her children, and followed finally by Rochel and Yosef. 33:2. Rashi says that the reason for this formation is 'acharon acharon chaviv', meaning that whoever is most dear goes last. [This phrase is commonly used in Jewish schools and homes, usually to assuage the feelings of a child who is last in line to receive something.]

The first pasuk of Parshas Nitzavim delineates all who were standing before Hashem. Rashi there says the order is determined by 'hachashuv chashuv kodem', meaning that whoever is most important goes first.

Why does chashivus/importance lead to being placed first whereas chavivus/endearment leads to being placed last - why wouldn’t being dear also lead to being placed first?

Perhaps our common understanding of 'acharon acharon chaviv' is not accurate. Rather, chavivus/endearment leads to whatever best protects that which is dear. Sometimes that might be first, sometimes last, depending on the situation. Here Esav is a threat, and Yaakov protects those most dear to him by leaving them in the back. In fact, Rashi makes his acharon acharon chaviv comment on the words describing Leah's placement in the middle, further bolstering the idea that there is nothing special about being last per se, unless the context calls for it as a protective measure.

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