What is the meaning of the old and the new wineskins in Luke 5:33-39?
In Luke 5:33-39, Jesus is talking about the Kingdom of God, and its specific realization in the church. The “old wineskin” is a metaphor for the Old Covenant, or it is the Jews who follow the Law of Moses, but are not willing to believe in Jesus. Jesus is telling us that the Old Covenant will not be gradually changed into the New Covenant, but the New Covenant in Jesus will completely replace the Jewish system. Jeremiah 31:31-35 is an Old Testament prophecy of the same thing. God tells us there that there will come a time when God will send a New Covenant–a better one–to replace the Old.
So, what Jesus is saying here is that he is not trying to reform Judaism but to bring in a new manifestation of the Kingdom of God which is entered by being born again. The Kingdom that Jesus anticipates is so different from what the Jews have been doing and it is so far beyond the Old Covenant, that it must be completely replaced, not changed gradually. The “old wineskin” of Judaism as practiced by Jews in Jesus’ time cannot be reformed. It must be replaced by the version of the Kingdom which we call the Church. In its very earliest phases the Christian church was, at least in a sense, there in Jerusalem, part of Judaism. However, very soon the Christians were kicked out of Jerusalem (at the end of chapter seven and the beginning of chapter eight of Acts) and kicked out of Judaism. Within a few years the Church was strongly persecuted by the Jews and a fully separate movement we call the Christian Church was begun. This is the new wineskin.
The controversy which caused Jesus to make this point in the context of the passage is over fasting. Those who were disciples of the Pharisees had various prescribed fasts. The followers of Jesus did not take part in these fasts. Although Jesus’ followers did obey the Jewish laws during his ministry, they did not acknowledge the extra teachings which had been brought in by the Pharisees. They had a new and greater Teacher whose authority outweighed that of the Pharisees. Eventually, Jesus and his ministry completely replaced the authority of the Pharisees. This new wine of the New Covenant could not fit within the restraints of the legalistic, Pharasaic practices of Jesus’ day.