Before Klal Yisrael left Egypt, they were given a special command: “Please speak in the ears of the people: Let each man request of his fellow and each woman from her fellow silver vessels and gold vessels.” [Shemos 11:2] This is why the Jews left Egypt extremely wealthy. They took the gold and silver from their Egyptian neighbors.
This was in fact a fulfillment of the Almighty’s promise to Avraham “Afterwards (i.e. – after the 400 years of being strangers and enslaved) they will leave with great wealth” [Bereishis 15:14]. In fact, the Talmud makes the point that Hashem had to “request” of Moshe that he “please speak in the ears of the people” so that it not be said that the years of slavery were endured but the promise of great wealth was not fulfilled.
Imagine the scene: The Jewish slaves were the trusted employees of their Egyptian masters for so many years. In fact, they were, of course, more than just trusted employees. They were more than workers, more than servants. We are talking about slaves! Now the slave knocks on the master’s door and says “You know what, I always liked that silver candelabra you have. Give it to me.”
Why did the Almighty set it up like this? His promise of great wealth could have come about in so many other ways. Just like the manna came miraculously and the water came miraculously, He could have sent us great wealth miraculously. Why did he give it to us in such a way that we had to “borrow” it and then not return it?
In the back of most Gemaras there is a famous commentary known as the RaShaSh – Rav Shmuel Shtarshon. He was not only an author (he wrote comments on every folio of Shas with the exception of 3) he was also a wealthy man and ran a Gema”ch (a free loan society). He once lent money to a tailor for a year. Payback time came and the tailor returned to the home of the RaShaSh with an envelope containing the money. He knocked on the door, Rav Shtarshon was busy writing his commentary so he came to the door, took the envelope, stuck it in the sefer [book] he was learning at the time and continued on writing his commentary. He then closed the book and completely forgot about the envelope.
A couple of months later, he reviewed his Gema”ch ledger and he saw that the tailor never paid back the money that he borrowed. He went to the tailor and asked for payment. The tailor insisted that he paid already. The RaShaSh had no recollection of the payment and continued pressing the man for repayment. Ultimately the RaShaSh took the tailor to a din Torah (a religious tribunal) to settle the matter. The court ruled in favor of the tailor. However, the general population did not believe the simple tailor against the great Talmid Chochom, Rav Shmuel Shtarshon. They boycotted his tailor shop to show their displeasure.
His business went down the drain. He could not make a living to the extent that he had to leave town. His life was ruined. One fine day, the RaShash picked up a sefer he had not learned from in many months. Lo and behold, he found the envelope with the tailor’s money. He was beside himself with grief. He sought out the tailor and begged forgiveness. However, the tailor was not willing to accept the apology. “It’s too late. I’m ruined already.” The RaShaSh insisted that he would go to the Beis Medrash, give a bang on the bimah and announce publicly “the tailor was right and I was wrong.”
The tailor said, “Tough. They will never believe you. They will say that you are such a great Tzadik, you just want to make me feel good and appease me, even though I really never paid you the money.” The RaShaSh then said, “No. There is something I can do for you. I have a daughter and you have a son who needs a shidduch. Your son is not a big Talmid Chochom and he is the son of a simple tailor, but if we become mechutanim, then everybody will know that you were right and I was wrong.” And that is what he did. He gave his daughter in marriage to the tailor’s son to rebuild the reputation and self-esteem of the man whose reputation and self-esteem he had sullied.
The matter with the “great wealth” at the end of the enslavement is similar. If the Jews had merely received miraculous compensation after 400 years of hard work and bitter enslavement, that would not have given them back the self-esteem that wore away during all those years of brutal slavery. Their payment had to come directly from the masters for whom they labored. It did not suffice to merely leave Egypt with their money. They had to leave with their pride as well. For that it was necessary to direct them to go knocking on the doors of the Egyptian masters and to take their finest items of gold and silver – because it was coming to them. Their masters owed it to them!
The side lesson to be learned here from the story of the RaShaSh is that when the Almighty wants a poor tailor’s son to find a prestigious shidduch [matrimonial match], then some way or another, He will make it happen!