Why Pharaoh Cried Woe When Israel Left Egypt

Midrash Tanchuma Buber, Beshalach 5:1

Another interpretation [of "And it came to pass when Pharaoh let the people go" (Exodus 13:17)]. Who cried "Woe" (vai)? Pharaoh cried "Woe." Rabbi Jonathan ben Eleazar said: To what is the matter comparable? To a man who had logs of cedar, and he sold them for a small sum of money. The buyer went and made from them chests and turret-shaped cabinets and many objects. That man who had sold them went out and saw those objects, and he began to lament, and he said: "Woe to that man! What has he sold!" So too with Pharaoh. Israel was enslaved to him with clay and bricks, and it was not recognized that they were a nation. As soon as they went out of Egypt and came and were made into banners at the sea, Pharaoh went out and saw them, that they had been made into banners. At that hour he began to cry "Woe": "And it came to pass when Pharaoh let the people go" (Exodus 13:17).

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Biblical References