“I will give him a portion with the great.” The Hebrew can also be translated as it is in the Christian Standard Bible: “I will give Him the many as a portion, and He will receive the mighty as spoil.” In that case, the Hebrew word “great” is translated “many,” which it can be. Although this translation is possible, the Hebrew grammar does make it slightly less likey than the way most versions translate the verse, and it does not seem to fit the context or scope of Scripture as well. This seems to be a case where just because a phrase can be translated a certain way does not mean it should be translated that way.
“because he.” Isaiah 53 closes with the reasons that God will give the Messiah a portion with the great. He “poured out his soul to death, and permitted himself to be counted among the transgressors.”
“he permitted himself to be counted among the transgressors.” The Hebrew text can be translated as a simple passive, that Jesus “was counted among the transgressors,” or it can be translated as a reflexive, that Jesus “permitted himself to be counted among the transgressors.” Although both statements would be true, the reflexive translation fits the context better, as this phrase is giving a reason that God exalted Jesus. This is not just a historical fact that he “was” counted with the transgressors, but the noble act that he allowed himself to be counted with them. Jesus voluntarily gave up his life for the sins of humankind (for more on the translation “permitted himself” see John Oswalt, NICOT: The Book of Isaiah, Chapters 40-66).
“Yet he himself carried the sin of many and made intercession for the transgressors.” The Messiah, Jesus Christ, carried the sin of many so that they would not have to carry them. The last phrase, “and made intercession for the transgressors” is both tied to the phrase about carrying the sins of many and yet is also separate from it. Jesus Christ made intercession for sinners by carrying their sins, but he went beyond that and continues to make intercession to the Father for the sinners. This is Jesus acting in his role as High Priest, and standing between the sinner and God.
Isaiah 53:12 concludes the Servant Song that started with Isaiah 52:13. [For more on the Servant Songs, see commentary on Isa. 42:1. For more on Isaiah 53 being connected with Isaiah 52, see commentary on Isa. 53:1].