Villains - Ishmael

(1) פרא אדם A WILD MAN — One who loves the wildernesses to hunt wild animals, as it is written (Genesis 21:20) “And he dwelt in the wilderness and became an archer.”

(2) ידו בכל HIS HAND SHALL BE AGAINST EVERY ONE — a highwayman.

(4) And how could it come into your mind that Abraham, of whom it is written: And Abraham was very rich in cattle, in silver, and in gold (Gen. 13:2), would have sent out his wife and son from his home, empty-handed, without clothes or food, silver or cattle? But rather, this comes to teach you that after Ishmael fell into depravity, [Abraham] no longer turned his mind toward him. But if this is so, what is meant by And the thing was very grievous in Abraham’s sight on account of his son? [It was grievous to him] that [Ishmael] fell into depravity. You find that when Ishmael grew up, he would wait at the crossroads to murder and rob the human beings, as it is said: And he shall be a wild ass of a man; and his hand shall be against every man (Gen. 16:12).

(3) ויד כל בו AND EVERYONE’S HAND AGAINST HIM — everyone will hate him and attack him.

...And these are the generations of Ishmael son of Abraham (Breishit 25:12). R. Khama bar Uqva and the rabbis were sitting and questioning: how did the text see fit to relate the generations of this evildoer here? R. Levi passed by and they said: He is the master of traditions, let us ask him. R. Levi said in the name of R. Khama: To let you know at what age your ancestor [Jacob] was blessed (Breishit 25:17). And these are the years of Ishmael's life. How did the text see fit to relate the years of this evildoer here? Because he came from the extremes of the wilderness to enact kindness for his father (Breishit 25:18).

(4) ועל פני כל אחיו ישכון AND HE SHALL DWELL IN THE PRESENCE OF ALL HIS BRETHREN — his progeny will be numerous, (so that his territory must extend over that which his brethren have; cf. Genesis 25:18).

...And here there was a caravan of Ishmaelites. Egyptians and Midianites and Ishmaelites - they were brothers from among the sons of Abraham's concubines: Ishmael son of Hagar and Midan and Midian from the sons of Qeturah. And in that same group there were some of the sons of Ishmael and some of the sons of Midan and some of the sons of Midian. Therefore it sometimes calls them Ishmaelites and sometimes Midanites and sometimes Midianites.

(2) את בשר ערלתו, the flesh of his foreskin; according to Rashi, Ishmael, although still a child, had to proceed and perform the circumcision on himself...

(1) מצחק MAKING SPORT — A term for worshipping idols, as it is said (Exodus 32:6) “And they rose up to make merry (לצחק).” Another explanation: a term for immoral conduct, just as you say (Genesis 39:17) “To mock (לצחק) at me.” Another explanation: a term for murder, as (2 Samuel 2:14) “Let the young men, I pray thee, arise and make sport (וישחקו) before us”. He (Ishmael) was quarrelling with Isaac about the inheritance, saying, “I am the first-born and will, therefore, take a double portion”. They would go into the field and he (Ishmael) would take up his bow and shoot arrows at him (Isaac), just as you say (Proverbs 26:18-19) “As a madman who casteth firebrands, [arrows and death] and says: I am only מצחק mocking” (Genesis Rabbah 53:11).