The Rabbis of the Midrash thought Pharaoh knew exactly how that felt when he finally let the Israelites leave Egypt.
Shemot Rabbah, a compilation of rabbinic interpretations on the Book of Exodus, dives deep into the implications of Pharaoh’s change of heart. It all starts with the verse, “it was when Pharaoh let the people go” (Exodus 13:17). But the Midrash doesn't just read the verse; it explores it.
To illustrate Pharaoh's predicament, the Midrash offers a parable, a mashal. Imagine a man who owns an orchard. He sells it for a maneh, a hundred dinar (a standard sum of money). What he doesn't realize is that his orchard is overflowing with riches: olive trees worth a hundred maneh, grapevines worth another hundred, pomegranate trees, spices… each and every species within the orchard is worth a fortune.
When the seller discovers the true value of what he sold, he's filled with regret. He didn't know what he had! Even if the orchard only had springs of water, as it is stated: “A spring of gardens, a well of spring water, and flowing streams from Lebanon” (Song of Songs 4:15), that would have been enough to justify a far higher price!
The Midrash then applies this parable to Pharaoh. Initially, he saw the Israelites as just a labor force, a group of slaves. Their freedom seemed like a small price to pay to end the plagues. But his advisors quickly set him straight, saying: “What have you done? If they had only the loot, that would suffice for them".
Think about it. The Israelites didn't leave empty-handed. Exodus 12:38 tells us “A mixed multitude, too, ascended with them, [and flocks and herds, even very much cattle]". And beyond the material wealth, there were the people themselves. As Song of Songs 4:13 puts it, “Your branches are an orchard of pomegranates.” Just as pomegranates are full of seeds, Israel is full of valuable assets: numerous wealthy people, wise men, artisans, men, women and children.
The Midrash draws a direct line to the book of Jeremiah: “The children of Israel and the children of Judah are oppressed…their Redeemer is mighty, the Lord of hosts is His name” (Jeremiah 50:33–34). The Israelites weren't just leaving; they were being redeemed.
The text emphasizes the anguish Pharaoh experienced when he realized what he'd lost. According to the Midrash, at that moment, when his advisors said: “What is this we have done, that we have let Israel go from serving us?” (Exodus 14:5), he began crying: “Woe, woe [vai vai].” "It was [vayhi] when Pharaoh let [the people] go.”
So, what’s the takeaway? This passage from Shemot Rabbah isn't just about Pharaoh’s regret. It's a reminder to recognize the true value of what we have, be it people, resources, or even our own potential. Sometimes, we don't see the richness within until it's almost gone. And sometimes, the redemption of others leads us to lament our own loss.