"And Saul, yet breathing out threatenings and slaughter against the disciples of the Lord, went to the high priest, and desired of him letters to Damascus to the synagogues, that if he found any of this way, whether they were men or women, he might bring them bound to Jerusalem.
Out of his anguish he shall see light; he shall find satisfaction through his knowledge. The righteous one, my servant, shall make many righteous, and he shall carry their iniquities. (53:11)
Despite the high cost, he can see the light and be satisfied with the outcome. I believe the NRSV makes the most sense of the phrase, following along with the readings of the LXX and the Dead Sea Scrolls. The servant is the righteous one. He has done no wrong. The offering of his life will make many righteous and he will carry away their iniquities. Again, many translations have “he shall bear their iniquities.” Just like in Isaiah 53:4, the word translated “bear” means “to lift, to carry.” The righteous servant will carry our iniquities, pronouncing the people innocent.
Therefore I will divide him a portion with the many, and he shall divide the spoil with the strong, because he poured out his soul to death and was numbered with the transgressors; yet he bore the sin of many, and makes intercession for the transgressors. (53:12; ESV)
The final picture pictures the servant in the role of a conqueror who has been victorious in battle. In his victory the servant will divide the spoils of battle. The apostle Paul explains the spoils of victory in Ephesians 4:8-12.
8 Therefore it says, “When he ascended on high he led a host of captives, and he gave gifts to men.” 9 (In saying, “He ascended,” what does it mean but that he had also descended into the lower regions, the earth? 10 He who descended is the one who also ascended far above all the heavens, that he might fill all things.)11 And he gave the apostles, the prophets, the evangelists, the shepherds and teachers, 12 to equip the saints for the work of ministry, for building up the body of Christ…. (ESV)
The spoils of victory that he gave to us so that we can also conquer Satan were apostles, prophets, evangelists, shepherds, and teachers so that every person can be equipped for the work and be built up in Christ. The servant was able to divide the spoils of victory with us because he poured out his life to death, allowing himself to be counted among the transgressors. He carried away the sins of many. Again, the word “bore” means “lifted, carried away, take away.” Notice the parallel made between “baring (carrying away) the sins of many” and “making intercession for the transgressors.” The carrying away of our sins is the same as the making intercession on our behalf.
The fulfillment of this prophecy occurs in an unusual place, in my opinion. Being numbered with the transgressors is not noted while on the cross, but when he is with his disciples just before the betrayal in Gethsemane.
35 And he said to them, “When I sent you out with no moneybag or knapsack or sandals, did you lack anything?” They said, “Nothing.” 36 He said to them, “But now let the one who has a moneybag take it, and likewise a knapsack. And let the one who has no sword sell his cloak and buy one. 37 For I tell you that this Scripture must be fulfilled in me: ‘And he was numbered with the transgressors.’ For what is written about me has its fulfillment.” 38 And they said, “Look, Lord, here are two swords.” And he said to them, “It is enough.” (Luke 22:35-38; ESV)
The NRSV says “he was numbered with the lawless” and the HCSB says “he was numbered with the outlaws.” The word “transgressors” literally means “without law,” so either of these are also acceptable. Carefully read the text and notice that Jesus says that they need to carry swords so that the scripture will be fulfilled that he was numbered with the transgressors. Therefore, outlaws might be a better translation, saying that he was with those who would appear to be violators of the law. This is a point worthy of deeper study.