R. Baruch Gigi (link):
If you take your neighbor’s garment as a pledge, you shall return it to him by sundown. For it is his only covering; it is his garment for his skin – in what shall he sleep? And it shall be, when he cries out to Me, that I shall hear, for I am merciful. (Shemot 22:25-26)
This is most surprising. The Torah goes out of its way, in a most unusual fashion, to explain and justify a law which appears even at first glance to be entirely reasonable: we are required to aid and support an unfortunate debtor who is forced to hand over his garment as a pledge. What is the meaning of the seemingly superfluous elaboration, emphasizing the distress of this unfortunate position in such dramatic terms?
I once heard the following explanation cited in the name of the Seridei Eish. We must not lose sight of what this law is actually talking about. The entire purpose of the pledge is to ensure that the debt will be repaid. Here, the Torah is commanding that at night you must return the pledge. In the morning, you will go back to the home of the debtor: “You shall stand outside and the man to whom you are lending shall bring out the pledge to you” (Devarim 24:11). In the night, you are to return the pledge again, and in the morning you take it back. And so the garment is passed backwards and forwards, every day and every night. Under these circumstances, is it reasonable to think that the debtor is going to repay the debt? Is the pledge fulfilling its purpose? It seems highly doubtful; if the whole arrangement is so convenient for him, why should the debtor pay?
We are forced to conclude that what the Torah is demanding is unreasonable and even unjust. In this situation, where the borrower is so poor that the garment that he gives as a pledge must be returned at night so he will have something with which to cover himself, the chances of a creditor recovering his loan are very low…
Continued here: link.