Tafsiran Ulangan 15:17: Rashi, Chizkuni, Ibn Ezra & Or HaChaim

עבד עולם [AND HE SHALL BE THY] SERVANT עולם — One might think that עולם has here its usual meaning: for ever! Scripture, however, states, (Leviticus 25:10) “[And ye shall sanctify the fiftieth year and proclaim liberty throughout all the land unto all the inhabitants thereof] and ye shall return every man unto his family”. Consequently, you learn that it (what Scripture terms here עולם), can only mean the period until the termination of that Jubilee cycle (Mekhilta; cf. Rashi on that verse),

ונתת באזנו ובדלת, “and you will thrust it (the awl) through his ear into the door;” the door frame is presumed to be made of wood and therefore can be pierced easily, as opposed to a door frame made of stone. (B’chor shor)

I have already given the reason for piercing his ear at the door [comment on Exodus 21: 6]. The reason Scripture mentions this again is that you owe him a debt when he goes free; but, if he does not want to go, you must pierce his ear instead.

ואף לאמתך תעשה כן AND ALSO UNTO THY MAID SERVANT THOU SHALT DO LIKEWISE — i.e. furnish her out of thy property. One might think, however, that Scripture puts her on the same level with the man-servant concerning the piercing of the ear too! It however, states, (Exodus 21:5) “And if the man-servant (העבד) shall plainly say, [I love my lord … then … his lord shall bore his ear through with an awl]” — so you see that a man-servant must have his ear pierced, but a maid-servant does not have it pierced (Sifrei Devarim 122:6).