Mercy to the irresponsible:

Chazal[1] state that one who does not have “Deiah/Comprehension” it is forbidden to have mercy on him, as the verse[2] states “Ki Lo am Ninos Hu, Al Kein Lo Yerachchamenu Oseihu.” This verse means to say that Hashem will not have mercy on Bnei Yisrael if they do not contemplate their wrongdoing and understand that their suffering is coming because of their sins.[3] Thus, Chazal is teaching us that one should not have mercy on a person who does not care to take responsibility for his actions. If one is the cause of his own failures and simply refuses to own up to it, there is no room for mercy on the person.[4] Alternatively, it is coming to teach us that if someone makes a request which in the long term is detrimental to the person, one is not to have mercy on him and give into his request.[5] In Chassidus[6] it is explained that whoever does not have “Deah” cannot show mercy to others and hence likewise he is not befitting of mercy. “Deaih” in this sense refers to a softened personality which is humble and openminded. One who is tough and haughty does not receive mercy. This level of mercy of G-d that comes with limitations, and is not awarded to one without “Deah” is Hashem’s lower level of mercy, mercy that is found in the Sefiros.[7] However Hashem has a higher mercy which gives mercy to all, even to one without “Deiah”. This higher level of mercy is called “Saar Reishei”.[8] The Rebbe Rashab once stated “If the Torah forbade having mercy on him, then how great is the mercy that one must arouse, that even the Torah forbids it.”[9]

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[1] Rebbe Ami in Brachos 33a

[2] Yeshayahu 27/11

[3] Radak Yeshaya ibid

[4] This can be seem clearly in the judicial system in which a person who pled not guilty and shows no remorse is bound to receive a harsher sentence than one who pleads guilty and shows remorse to the court and victims.

[5] Margaliyos Hayam on Sanhedrin 92a, based on Sefer Chassidim and Leket Yosher

[6] See Likkutei Torah Bamidbar 3; Behalosecha 35b; Or Torah of Maggid 499

[7] See Likkutei Torah Tzav 12

[8] Likkutei Torah Devarim 1

[9] Brought in Toras Menachem 7/210; 10/231