The Parable of the Wineskins

The sequence of events that lead up to Jesus narrating the parable of the Wineskins is found in all three synoptic Gospels. There is some ambiguity when it comes to who originally questioned Jesus but this is one of the rare events that was captured in the same chronological order by all three writers. According to Luke, the Pharisees raised the question about fasting while John writes that it was the disciples of John the Baptist asking the question, and Mark does not explicitly mention any particular group but this is the only variation in all their narrations. All of them placed the narration of the Parable after Jesus had called Levi to be His disciple and had dinner at his house with his other tax collector friends.

Jesus was making disciples left right and centre calling even those who previously would have been overlooked by the Jewish community as unworthy of mentorship. It was during this time that the disciples of the Pharisees and John the Baptist came to Him, questioning about His associations with sinners and why His disciples were exempted by rules that they lived by. Jesus responded to their accusations by reminding them why He had come down to our world.

The Friend of Sinners

Just like the sick are the ones who really need a doctor, it is the sinners who truly need God. God sent Jesus for the sins of the entire world as all have sinned and fallen short of His Glory but some sects of the Jewish community refused to label themselves as sinners and thereby rejected the gift from God for their healing (salvation). Taken aback by Jesus’ response, they quickly came up with another point to bring Him and His disciples down.

“How is it that John’s disciples and the disciples of the Pharisees are fasting, but yours are not?

Mark 2:18 (NIV)

The disciples of the Pharisees and other Jewish leaders were bound by the traditions that were passed down for thousands of years with each generation adding to them their own set of laws. To them, righteousness was attained by one’s adherence to the laws rather than the grace of God. They strictly followed all the laws mentioned in the scriptures and the traditions of their ancestors blindly and believed that heaven was guaranteed to them. But they deemed their countrymen unrighteous and even classified some as irredeemable such as Levi the tax collector. To them, Jesus narrated the Parable of the Wineskins.

“No one pours new wine into old wineskins. Otherwise, the new wine will burst the skins; the wine will run out and the wineskins will be ruined. No, new wine must be poured into new wineskins.

Luke 5:37-38 (NIV)

Wine and Wineskins

Jesus used everyday objects like wineskins and articles of clothing to help His audience relate to His teaching. The Jews knew very well that storing new wine in old wineskins would be disastrous as the tartaric and malic acids found in them would break the wineskin. To handle fresh wine they would always use a new wineskin as the container would gradually adapt to the molecular composition of its contents. Similarly, in the case of garments, they would not use an old cloth to patch up a new one as they knew that the structurally weak old material will also pull apart and tear the newer cloth that it had been sown to. They knew that the wineskins needed time to mould to the wine rather than pouring age-old acidic wine into new wineskins. If they had paid half as much attention to the people who came to them, they would not have treated them with such apathy.

A modern rendition of the wineskin

The wineskins represented God’s people and the wine represented the set of beliefs that have moulded them. Some were newly welcomed believers while some have known Him throughout their lives. Pouring the beliefs that guide the lives of old believers into new believers will only lead them to eventually burst at the sight of the daunting task that lies ahead of them. The disciples never experienced closeness with God in all their lives like they did when they started travelling with Jesus. They were neither religious nor did they know the scriptures by heart. Most of them were even uneducated fishermen. Jesus was teaching them the way of His Father day by day and did not burden them with something they did not understand just yet.

And no one after drinking old wine wants the new, for they say, ‘The old is better.’

Luke 5:39 (NIV)

Jesus himself is not proclaiming that old is better but simply stating the fact that everyone prefers the older wine over the much tarter new wine. Jesus was addressing the fact that the new message that He had brought was not accepted by the old hardened hearts of the Pharisees and the teachers of the Law as they would much rather live in ignorance depending on their old laws and traditions to carry them through to their eternal dwellings. To them, their traditions and customs seemed much easier as they offered them familiarity and an assured path to heaven according to their beliefs. The way that Christ was proposing is crowded as it is full of sinners and did not offer them the guarantee they needed but simply asked them to have faith in God and rely on His grace. Even today, prayer and revival meetings are given more focus than for people to simply pick up their Bibles daily to know the heart of God. They would much rather be involved in visible acts of righteousness than spend a few moments of personal time with God behind closed doors. The old ways are preferred by people than the new radical way that Christ is teaching by simply depending on Him for guidance.


The Pharisees were brought up in the laws and traditions and expected everyone around them to follow their ways. Sometimes we treat the new believers in our church with the same contempt. God has an individual plan for every soul and by enforcing our thoughts on someone, we might break their spirit and end up reversing the good work God has been doing in their lives. When we ask a new believer to start fasting or give up something that we ourselves took a while to let go of, we are looking for ways to drive them away. Even the Jews of the early Church expected the new believers to circumcise themselves according to their own traditions (Acts 15) without giving any thought to what God wanted for them. Like the four friends who brought the paralyzed man, our work ends with bringing someone to Christ. Once we have made the connection between them, we must trust the Holy Spirit residing in the believer to handle their transformation according to the will of God for their lives.

Questions Discussed

  • Why were the Pharisees (or John’s disciples) concerned about Jesus’ disciples not fasting?
  • What is the purpose of fasting?
  • Do people fast blindly without knowing its purpose? Why would someone put their bodies through that without being sure of why they are doing it?
  • Why is Jesus responding with parables about wineskins and cloth? (Meaning of the parable, characters represented by age of the wineskins and of the wine etc.)
  • Why does Jesus say at the end that “old is better”?
  • What can we learn from this Parable?


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