“Eisav is still crying.” Since the time that Yaakov received the brochos from Yitzchak, Chazal say that Eisav has never stopped crying. This is surprising for two reasons. Firstly, if we look at the pesukim, it would appear that Eisav received virtually the same brocho as Yaakov. Secondly, if there was a slight difference, why can’t he get over it? It’s been a long time. Eisav has enjoyed mighty empires over the years which we never had. Why does Eisav still cry?
Firstly let’s look at the posukim. Yitzchak blessed Yaakov as follows: “May Hashem give you of the dew of the Heavens and of the fatness of the Earth, abundant grain and wine. Peoples will serve you and regimes will prostrate themselves before you. You should be a lord to your brothers and the sons of your mother will bow down to you; cursed be they who curse you and blessed be they who bless you.”(Bereishis 27:28-29). Yitzchak blessed Eisav as follows.” Behold of the fatness of the Earth shall be your dwelling and of the dew of the Heaven from above. By your sword you shall live but your brother you shall serve; yet it shall be that when you are aggrieved because Yaakov is not worthy, you may cast off his yoke from upon your neck. (ibid 39-40) They both received dew. The fatness of the Earth which Eisav was blessed with presumably includes the same abundant grain and wine that Yaakov was blessed with. Yes, Yaakov was blessed that he should rule over his brother but Eisav was told that if he is aggrieved he will be able to cast off the yoke of Yaakov. So why the tears?
Gemoro Succah (28b) compares rain on Succos to a servant who brings a cup of wine to his master and the master pours a jug of water over him. The Vilna Gaon (Kol Eliyahu Emor) asks why the Gemoro doesn’t say simply that the master throws the cup of wine over the servant? Why bring the jug of water into the moshol? He gives an illuminating answer. Hashem has arranged Succos after Rosh Hashono and Yom Kippur because He loves us. As we know, Rosh Hashono and Yom Kippur are days when we are being judged. It could be that we have davened sincerely, tried to do teshuva sheleima, committed ourselves to do better next year but alas at the final count, after Neila, our merits are not quite enough. Our aveiros still outweigh our mitzvos and Hashem has no choice but to respond with harsh judgement. But He loves us and wants to give us a last chance. Therefore Hashem gave us the mitzvos of Succah, arba minim, simchas Yom Tov (which women are also obliged to fulfil) as a way of diluting the judgment which He would have had to bring on us. There are so many mitzvos which we can do over Succos that we have an excellent chance to add enough merits to tip the scales of justice in our favour. Hashem’s desire to ‘dilute’ our judgment is symbolized by the water in the Gemoro’s moshol. If Hashem makes it rain (this is clearly talking about Eretz Yisroel where it rarely rains, not a country where rain is frequent anyway) and thus denies us the opportunity to fulfill the mitzvah of Succah, it is like the water, which was ready to dilute the strong wine into a pleasant drink, being thrown over the servant. The undiluted wine, which symbolises strict judgement, will now remain unpalatable. The main inspiration of this explanation, however, is how much Hashem loves us and wants us to deserve to be blessed with a successful year. He decrees a Yom Tov with its many mitzvos just at the moment that the merits acquired can tip the scale of judgment in our favour.
In Tehilim (149) we are told to “sing a new song…rejoice…praise His Name with dancing…make music with drums and a harp… because Hashem loves His People.” This could be a hint to Succos, according to the Vilna Gaon’s explanation. On Succos we can particularly appreciate how much Hashem loves us, wants us to be successful in judgement and wants to bless us. Of course we love Hashem in return and want to play our drums, harp, and other musical instruments to dance and sing in His honour which may hint to the simchas beis hashoeva of Succos.
True, Eisav’s dew, grains and wine etc were equal to Yaakov’s. That is not what Eisav cries about. He cries that Yaakov receives his blessings from Hashem: “Veyiten lecho Elokim”, whereas in his brocho the name of Hashem is not mentioned, as the Sfas Emes points out. Eisav’s brochos will come but without Hashem’s love. He might rule empires but will have no connection to Hashem. His life will lack the sweetness which a connection with Hashem produces. No beauty of Shabbos. No joy of Yom Tov. No inspiration from the Torah. A spiritual vacuum.
Yaakov was told that Hashem will bless him. His descendants will always feel His closeness. And this is the greatest brocho, which gives the greatest simcha. No wonder Eisav still cries.