Oh it makes "perfect sense". At least from a hard Christian perspective. Since Jesus failed all of the actual messianic prophecies those hard Christians had to invent their own. What better way that o quote mine one's own holy book? Who cares that the context always shows that it was not Jesus. When one has a need to believe one does not care about context.
In the NT, Jesus goes into the desert too fast and pray, before he began his ministry. There Jesus was tempted by SATAN, who among other things, offers Jesus all the wealth and power of the kingdoms of the earth. Had Jesus accepted this offer, he would have become the Messiah that was anticipated by the Jews. He would have had the power to do anything on earth including liberating the Jews from Rome since he would own Rome. Jesus could have become the anticipated Messiah, but chose not too.
Had Jesus accepted the offer, he would have had to bow down and serve Satan instead of God; chain of command. Satan was the Lord of the Earth in the OT and NT. Jesus never says Satan does not had this authority to make him the anticipated Messiah, since he knew he did. Instead by declining the offer, Jesus creates a political conflict in heaven, from which Satan is ultimately thrown from heaven. Jesus had the guts to challenge the authority of law and it's author, Satan.
Law is connected to the tree of knowledge of good and evil, which is the tree of Satan. All forms of law; religious, civil and secular, all break down behavior into good and evil; binary or Satan. God never condoned the tree of knowledge of good and evil as an option for Adam and Eve and humans. That was Satan's tree and law had many pitfalls leading to death and suffering. After the fall, Satan was given authority over humans and the Earth, since they chose each other. See book of Job, where Satan is the CEO in charge of humans and God is the Chairman of the Board. Suffering comes to the world because of original sin and law and Satan being in charge.
When Jesus dies for our sins, he comes in direct conflict with Satan, since sin is only imputed where there is law. If you do away with sin, even by forgiveness, you also do away with law. Laws without sin are no longer laws, but become guidelines. Guidelines have no teeth, but can still teach and inform, but without judgment and punishment.
An analogy is you are speeding on the highway, and a police officer pulls you over. Since you broke the law the wage of your sin should be a fine. You are ready to be punished by the law. But the patrol officer does not give you a fine, but forgives your transgression, and lets you off with a warning. He tells you the speed limit is for your safety, not a way to make money or an excuse to punish you. Forgiveness of sin has the same end result, as no law. In both cases, there is no punishment, but the hope you will drive safely.
The sacrifice of Jesus for sin, brought all forms of law into question. This brought into question the authority of Satan, who was author of all law and punishment via knowledge of good and evil. This leads to a political battle in heaven and Satan is thrown from heaven; Revelations. When Satan is relieved of his authority in Heaven, Law is no longer condoned by heaven, but now is only man made and subjective. The righteous man shall live by faith, apart from works of law, since law is now only heavenly guidelines without teeth. Faith may bring one on both sides of the fence, so one can learn all things, without punishment. However, human law still exists via Satan.
The suffering Servant in Isaiah is from the future. He is the sensible slave whose master put him in charge to get things ready for this return. He comes after Satan is thrown from heaven. He is the son of the Divine Woman who is in labor and pain about to give birth. Satan is nearby, ready to devour her child, but the child is caught up to God and protected.The suffering Servant's mother is sent away with the wings of an eagle pursued by Satan. She lands waiting for her wings to be clipped. Satan leaves her to torment others.
The job of the Servant is to prepare the way for the return of the son of God, who is now the new Lord of the Earth, after Satan gets the boot. Symbolism suggests that the Servant is the White and then the Red Horseman of the Apocalypse. His end game is to become a human sacrifice for guilt; one of the two anointed ones.
Although sin had been forgiven by Jesus, and law had been neutralized into heaven as guideline, via faith, there was still guilt for not always taking the optimized or common sense path, when faith led you the wrong way, for a lesson of life. The guilt sacrifice addresses this human pitfall of faith. If there was no guilt, then one can truly live by faith, without overthinking due to guilt.
Although this change is evolutionary to faith, it leads to the rise of the Anti-Christ. He perverts the message of the sacrifice of guilt and uses it to justify all forms of evil intent. The Servant appears again, at the very end, as faithful and true, leading the armies of the Lord.