Why does it say "Al Tirsha Harbe" - may one do a little evil?!
Torah Temimah citing Shabbos 31b: If one ate garlic and gives off an offensive smell, should he eat more garlic and give off more smell?! (One who sinned a little should not sin more.)
Rashi (16, citing Yuma 22b): When Sha'ul questioned why we should kill animals and children 1 of Amalek, a Bas Kol (voice from Heaven) said "Al Tehi Tzadik Harbeh 2 " (16). When he told Do'eg to kill the Kohanim, a Bas Kol said "Al Tirsha Harbeh 3 ." R. Avigdor - whoever is merciful on the cruel, in the end Midas ha'Din will strike him - "va'Yamas Sha'ul" (Shmuel I, 31:6).
Rav Sadya Gaon: Do not be drawn in evil.
Rashi: Even if you did a little evil, do not increase to do evil.
Ibn Ezra: This 'evil' is engaging in worldly matters. Much of it brings a person to danger. Engage [only] in what will suffice for you.
Rashbam: Do not be Sechel, and used to doing evil.
Ri Kara #1: Do not say, since I already sinned, I will enjoy the world and sin more.
Ri Kara #2: A Kal v'Chamor teaches this. Tzedek and Chachmah are eternal life, yet if overdone, they ruin him - "Al Tehi Tzadik Harbeh v'Al Tischakam Yoser Lamah Tishomem" (16) - all the more so evil and folly, which are always ruinous, and shorten man's years and make him die prematurely, we must warn about them "Lamah Samus b'Lo Itecha"!
Rid: Just like I warned you not to be too Tzadik, so I warn you not to be too evil - to pursue women, not to be concerned for Dam Nidah, and to eat meat without concern for Chelev and blood.
R. Avigdor: Do not go much with Resha'im - "Bni Al Telech b'Derech Itam
R. Avigdor: He said, Shmuel told me to destroy "ha'Chata'im Es Amalek" - if man sinned, did the animals sin?!
Seforno, Maharsha (22b): I.e. do not have mercy on Resha'im. Ri Kara - for this, his kingship was removed and given to David.
Do'eg killed "me'Olel v'Ad Yonek v'Shor va'Chamor va'Seh" (Shmuel I, 22:19)!
Metzudas Tziyon: This is like "uv'Chol Asher Yifneh Yarshi'a" (Shmuel I, 14:47).
What is being Sachel?
Ri Kara: It is saying 'since excess Chachmah makes one desolate, why should I get wise?' The verse warns against this.
Rid: It is being foolish. Just like I warned you not to be too wise, I warn you not to be too foolish, to pursue Havlei ha'Olam in eating, drinking, nice clothing and a nice dwelling, without concern for the Creator at all.
Seforno: It is to veer totally from engaging in temporary life, even in order to engage in Torah and Mitzvos.
Metzudas David: It is to totally ignore something terrifying.
What would cause you to die before your time?
Rav Sadya Gaon: You will be Chayav Misah before it was time for you to die [Rashbam - if you do much evil].
Rashi: This is like Sha'ul - "va'Yamas Sha'ul b'Ma'alo Asher Ma'al" (Divrei ha'Yamim I, 10:13) - [he transgressed with] Nov Ir ha'Kohanim and Amalek.
Ibn Ezra: Sechel (folly). Rid - refer to 7:17:2:2.
Seforno: If you veer totally from engaging in temporary life; you will not get temporary life, and not Torah and Mitzvos.
Metzudas David: Excessive panic, or totally ignoring the terrifying danger.