Why is the word "Kesusoh" written with a 'Hey'?
Moshav Zekenim: To teach us that if the borrower owes a hundred Zuz and his garment is worth two hundred, we do not tell him to sell it and buy an inferior one worth a hundred Zuz, and give the creditor the hundred in payment of his debt. 1
R. Shimshon Refa'el Hirsh: The feminine shows that we should take into account his weak, downtrodden state.
See Torah Temimah, note 208, who learns this from the word "Simlaso", which implies an expensive garment. Moshav Zekenim: Nowadays however, we rule like R. Tam, that we do not leave a borrower with his basic needs.
What are "Kesuso", and "Simlaso le'Oro" referrng to?
Rashi, Targum Yonasan and Mechilta: "Kesuso" refers to his cloak, and "Simlaso", to his under-shirt.
Having specified the top and the under-garments, what is "ba'Meh Yishkav" referring to?
Rashi, Targum Yonasan and Mechilta #1: It refers to his leather matress. 1
Mechilta #2: It includes all Keilim. 2
Hadar Zekenim: 'I command you to return it to him, because with what will he go to sleep?"
Refer to 22:26:151:1 and See Torah Temimah, note 207.
It is not clear however, why the Torah needs to mention all three.
What are the implications of "ve'Shama'ati ki Chanun Ani"?
Ramban: It teaches us that if someone cries out to Hashem with all his heart, Hashem listens to his cries, even if he is not worthy. 1
Rashbam and Riva (citing R..M. of Kutzi): Strictly speaking, the creditor has a security (which he owns). His obligation to return it is Lifnim mi'Shuras ha'Din (beyond the letter of the law), in which case, when the creditor fails to return it, Hashem ought to ignore his cries - and it is only because Hashem is gracious that He answers him. 2
Seforno: Even though the poor man has no basic claim against you, since he borrowed from you and owes you money, Hashem will listen to his cries because you left him without clothes, following which He will deduct part of the extra money with which He graced you to provide others less fortunate than yourself, and give it to him. 3
Moshav Zekenim #1: It implies that since 'I will listen to his cries because I am gracious' you too should be gracious and go beyond the letter of the law, and return his security.'
Moshav Zekenim #2 (citing R. Asher): It implies that one should not say that I (Hashem) will not take a Tzadik's garment [as a security], but I will take the garment of a Rasha - because 'I am gracious, and I hear the cries of everyone'.
Moshav Zekenim #2, Da'as Zekenim #1 and Hadar Zekenim #1: It implies that when the Ani will cry out joyfully 4 to Me - on account of the good that you did to him by returning his security and bless you ("Veshachav be'Simlaso u'Veracheka"), I will listen to him and bless you, because "I (Hashem) am gracious'.
Mechilta: It implies that 'I will hear his cries, because I created the world with Midas ha'Rachamim' - and you should take your cue from Me'. 5
Because 'Chanun' is a derivative of the word 'Chinam', implying that when one supplicates to Hashem, He responds with a Matnas Chinam, irrespective of one's credentials. See also Rashi at the beginning of Va'eschanan.
Rashbam and Riva: As opposed to Pasuk 22, in connection with an Almanah and a Yasom, where the Torah does not use the Lashon "Chanun" - because they are crying out to Hashem min ha'Din.
You are therefore well-advised to return him the security in its time, thereby ensuring that Hashem continues to grace you with the extra money to continue providing those in need.
Tza'akah (crying out) is sometimes from Simchah (Malbim Tehilim 17:1. - PF)
Hadar Zekenim and Da'as Zekenim: The Oni's cry is 'I was created in Your form like him - he lies in comfort in his bed, and I do not have what to lie in!' However, this is difficult, for we do not find "Chanun" for evil. See also Torah Temimah, note 209, who elaborates.
QUESTIONS ON RASHI
Rashi writes that here the Torah is discussing a day garment, Then why does it write "ba'Meh Yishkav"?
Moshav Zekenim: Because although the previous Pasuk is discussing a day garment, the current Pasuk is discussing a night garment. 1
Even though (Devarim 24:13) "Hashev... Veshachav be'Simlaso" discusses a night garment that is needed to teach us that the lender acquires the security. Moshav Zekenim: As the Torah writes there "u'Lecha Tih'yeh Tzedakah". See also Torah Temimah, note 207.
