The parable of the new wine in old wineskins appears in Luke 5:36-39. Why did Jesus tell this parable? What does it mean? Here is my take on it.

Jesus told this parable at Luke 5:36-39 when he was at the reception threw by Levi the tax collector.
36 And he spake also a parable unto them; No man putteth a piece of a new garment upon an old; if otherwise, then both the new maketh a rent, and the piece that was taken out of the new agreeth not with the old.
37 And no man putteth new wine into old bottles; else the new wine will burst the bottles, and be spilled, and the bottles shall perish.
38 But new wine must be put into new bottles; and both are preserved.
39 No man also having drunk old wine straightway desireth new: for he saith, The old is better.
Luke 5:36-39
At this reception, the Pharisees and scribes complained about two things regarding Jesus and his disciples.
- Jesus mix around with sinners and tax collectors
- Jesus eat and drink all the time and do not fast and offer prayers unlike John the Baptist
The reply to the first question is a familiar one. Jesus said that he has not come for those who are well but for those who are sick. He has not come to call the righteous but sinners to repentance.
The reply to the second question is that this is the time for celebration because He is with them. Fasting time will come when He is taken away from them.
Since He has already addressed the complaints, why did He tell the parable?
This is because the two complaints are not the crux of the issue. And Jesus wants to address the actual root cause.
The Pharisees were treating Him like any other prophets and trying to fit him into their existing religious system. Staying away from sinners, and fasting and praying are what religious leaders do.
A perceptive Pharisee would be able to tell from the parable that Jesus is refusing to be part of the existing system. A brand new system is what He is bringing. A system that will not tolerate the old.
The New and Old Garments
I have always thought that this parable refers to patching the old garment as if there is a tear that requires repairing. It is probably from my own cultural background. My grandmother repaired our clothes when they are torn by patching them with pieces of cloth.
However, a more attentive and slower read showed that I was wrong. There is no mention that the old garment was torn.
Yes, it is an old garment, but it was wearable. No tears. No holes.
He said that no one would do that, that is, cut a piece from a brand new garment and sew it onto an old garment. This will ruin the new garment.
But what in fact he is saying is, the Pharisees are trying to do just that. He is the new garment and the Pharisees’ system is the old garment. They are trying to take bits of what He is and add to their existing system.
It wouldn’t work.
New Wine in Old Wineskins
To reinforce this, Jesus used another common everyday object to put his point across. Wine!
No one put new wine in old wineskins. Jesus is the new wine and the Pharisees’ religion is the old wineskins. Jesus is calling out the Pharisees’ desire to fit Him into their agenda. The outcome is that the old wineskins will burst. It will be ruined. The wine will be spilt. It will be ruined too.
If I was a Pharisee back in Jesus’ time, I will be very uncomfortable with what Jesus said. Like a thorn in the flesh that cannot be ignored. He said that there is no way He would join us and that the current Pharisaic system is not great. He gave me no leeway to manoeuvre. This really leaves me not much choice. It is either admit my mistake (which could mean denying my entire life) and join Him or get rid of Him.
Jesus predicted that the Pharisees would choose to get rid of Him.
He ended the parable by saying that no one after drinking the old wine wishes for the new wine. People who have accepted the old wine as good wants to switch to the new wine.
Have you heard of this saying,
“Good is the greatest enemy of the great”
I think Jesus antagonized the Pharisees on purpose. He didn’t have a shouting match with them. He merely quietly told them a parable and embedded the hard truth in it.
What can the Pharisees do? Fume and plot in secret I guess.
Jesus is so cool.