The reason it is difficult to sleep on Motzaei Shabbat [Saturday night] is because the revelation of Elijah the Prophet begins then. As our Sages of blessed memory taught (Eruvin 43b): Elijah does not come on Shabbat or on Erev Shabbat, but he may come on Motzaei Shabbat. Thus, from that time, the revelation of Elijah begins.
And our Rabbis taught (Eduyot, ch. 8) that Elijah comes only to distance those who were brought near by force [i.e., improperly], and to bring near those who were distanced by force [i.e., improperly rejected]. This means to distance falsehood and to draw close truth.
As taught in the Zohar (Zohar, Tisa 188a): A heretic asked, “It is written, ‘The lip of truth shall be established forever’” (Proverbs 12:19). Rabbi Elazar answered: It does not say “kunanta” [you have established] but rather “tikon” [shall be established], because truth will only be truly established in the future—when Elijah and the Messiah come (cf. Jeremiah 23). Then the verse “The lip of truth shall be established” will be fulfilled, meaning falsehood will be pushed away and truth will be drawn near.
And our Sages said (Shabbat 104a): Falsehood is close to him, but truth is distant from him. Therefore, Elijah will come to push away the falsehood, which is the aspect of the serpent(Genesis 3:14). And the serpent brought death into the world. Sleep is one-sixtieth of death (Berakhot 57b).
Since Elijah’s revelation begins on Motzaei Shabbat, and he pushes away falsehood—the aspect of the serpent—therefore, it becomes difficult to sleep.
For our Rabbis said (Kiddushin 49b): “Ten measures of sleep descended into the world; nine were taken by slaves.” And a slave is the aspect of “Canaan, servant of servants” (Genesis 9:25), which is also called “cursed”—an aspect of the serpent.
Therefore, since on Motzaei Shabbat the aspect of Elijah is revealed, and the aspect of the serpent (i.e., Canaan the slave) is pushed away, the sleep that descended to the slaves is also pushed away. “Elijah” is numerically equal to “son” (ben)—the opposite of a “slave.”
Additionally, our Sages said: “If there is no understanding, from where comes separation?” (Yerushalmi Berakhot, ch. 5). It follows that the separation made on Motzaei Shabbat [Havdalah] is in the aspect of understanding. Therefore, it is difficult to sleep, because sleep involves a removal of understanding.
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