Yet it pleased the LORD to bruise him; he hath put him to grief: when thou shalt make his soul an offering for sin, he shall see his seed, he shall prolong his days, and the pleasure of the LORD shall prosper in his hand.
Transition from His humiliation to His exaltation.
Yet it pleased the Lord - the secret of His sufferings. They were voluntarily borne by Messiah, in order that thereby He might 'do Yahweh's will' (John 6:38; Hebrews 10:7; Hebrews 10:9), as to man's redemption; so at the end of the verse, "the pleasure of the Lord shah prosper in His hand."
Bruise - Hebrew, dak'ow (H1792) (see Isaiah 53:5, the same Hebrew, "He was bruised for our iniquities"); Genesis 3:15, was hereby fulfilled though the Hebrew word yªshuwpkaa (H7779) for "bruise," there, is not the one used here. The Hebrew there may mean to overwhelm with darkness. Messiah's time of darkness was temporary (Matthew 27:45), answering to the bruising of His heel. Satan's is to be eternal, answering to the bruising of his head (Isaiah 50:10).
He hath put him to grief - recapitulating Isaiah 53:4, "He hath borne our griefs" (the same Hebrew as here, hechªliy (H2470)).
When thou shalt make his soul an offering for sin ( taasiym (H7760), second person singular masculine) - rather, as mary. (Hebrew, third person feminine), 'when His soul (i:e., He) shall have made an offering for sin.' In the English version the change of person is harsh: from Yahweh, addressed in the second person (Isaiah 53:10), to Yahweh speaking in the first person in Isaiah 53:11. The margin rightly makes the prophet, in the name of Yahweh Himself to speak in this verse. Thus translated, the clause indicates the Saviour's voluntary laying down of His life (John 10:17-18; Ephesians 5:2; Hebrews 9:14). So the Vulgate.
Offering for sin - (Romans 3:25; 1 John 2:2; 1 John 4:10); asham, sin, with reference to its guilt and penalty. So a sin offering 2 Corinthians 5:21 accords with the English version, "He (the Father) hath made Him (the Son) to be sin for us, who knew no sin, that we might be made the righteousness of God in Him."
He shall see his seed - really His seed, not in mere figure, because they derive all their life from Him (1 Peter 1:3). His spiritual posterity shall be numerous (Psalms 22:30); nay, more, though He must die He shall see them. A numerous posterity was accounted a high blessing among the Hebrews; still more so for one to live to see them (Genesis 48:11; Psalms 128:6).
He shall prolong his days - also esteemed a special blessing among the Jews (Psalms 91:16), in contrast to His past shortening of life as one "cut off out of the land of the living." Messiah shall, after death, rise again to an endless life (Psalms 21:4; Hosea 6:2; Romans 6:9).
And the pleasure of the Lord shall prosper in his hand - that "pleasure of the Lord" to which the opening words of the verse allude: "it pleased the Lord to bruise Him." Compare Colossians 1:19-20; Ephesians 1:9-10; Isaiah 52:13, margin.