Eisav’s tears have had a significant impact on the fate of Klal Yisrael. We have been considered unscrupulous for stealing Eisav’s birthright. Eisav was rewarded for his tears. He experienced peace and tranquillity as a result of his weeping. Moreover, the Zohar Hakadosh says that Moshiach will not come until Eisav’s tears will dry. This is the analogy: We will remain under Eisav’s power until we repent and shed tears that will overwhelm Eisav’s tears. What do Chazal mean by this? Ostensibly, Klal Yisrael has long ago surpassed the level of Eisav’s tears. What aspect of his tears condemned us so?
Eisav was sincere when he cried. He wept for the blessings that he had lost. He wept for something positive that now eluded him. What do we cry about? Do we cry because we cannot perform mitzvos properly? Do we cry because we cannot understand the Gemara? Eisav wept for blessings. We weep for the pain and suffering which have accompanied us throughout history. We may learn how and what to cry for–from Eisav. When we demonstrate that same sense of loss over mitzvos and berachos as Eisav did, then our tears will overwhelm his. It is not the quantity of our tears, but their catalyst that is important.
