New Wine in Old Wineskins: Matthew 9:17; Mark 2:22; Luke 5:37-38
The parable of the new wine in old wineskins has the same meaning as the Parable of the Unshrunken Cloth on an Old Cloak. Jesus mentions both together, as part of his answer to the question: Why do your disciples not fast when disciples of other teachers do fast?
Similar to the situation with the unshrunken cloth, wine will expand as it ferments. When fermenting wine is placed in new wineskins (made from animal skin), the wineskin expands with the wine.
However, old wineskins have already been stretched. Meaning, if someone fills an old wineskin with new wine, then the old wineskin can no longer expand and it will burst.
The first part of Jesus' answer is "You cannot make wedding guests fast while the bridegroom is with them, can you?" (Luke 5:34)
Jesus is making a statement about himself, alluding to the fact that God is establishing a new covenant with the world, just like when a covenant is established at a wedding.
Jesus says he is the bridegroom, and the wedding guests certainly do not fast while the bridegroom is still present.
He further elaborates on this point by telling the parable of the new wine in old wineskins, teaching that something new is happening and it cannot be mixed with the old. Jesus is essentially saying, 'My disciples are not fasting because God is in the process of establishing a new covenant.'
Neither Jesus' disciples, nor those asking this question, fully understood at the time what Jesus was implying. Only he understood the significance of himself and the current times, which is why many were confused by his parables.
This is why Jesus asked his disciples, "Who do you say that I am?" (Matthew 16:15; Mark 8:29) No one was certain who Jesus Christ was at that time. Some people thought he was John the Baptist, Elijah, or Jeremiah. It was only Jesus' disciples who slowly began to realize that Jesus was God's messiah.
However, now that we know who Jesus is, it is clear Jesus made a very serious statement about what God is doing in the world and used this parable of the new wine in old wineskins to illustrate it.
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