Luke 5:33–39: Old Way Gone

July 13, 2026

The Ten Signposts of the Bible
CAMDE—400—CALY
Creation. Abraham. Moses. David. Elijah. 400. Christ. Apostles. Letters. Yet-to-Come.

The first year of Jesus’ ministry is often called the “Year of Popularity.” As Jesus taught in the synagogues, Luke says, he was “being glorified by all” (Luke 4:15). When Jesus healed the sick and cast out demons, “amazement seized [the people], and they glorified God and were filled with awe, saying, ‘We have seen extraordinary things today’” (Luke 5:26). 

The religious leaders were among the crowds as well. It appears that the higher-ups in Jerusalem sent a delegation to investigate this new teacher in Galilee who was drawing such large numbers (Luke 5:17). Although they could not deny Jesus’ power to cast out demons, heal a man “full of leprosy,” and restore a man who had been paralyzed, they were critical of his message and his interactions with the people. 

When Levi, a despised tax collector, chose to follow Jesus and hosted a banquet to introduce him to his friends, the religious leaders first grumbled about Jesus associating with sinners. Then they accused him of enjoying the celebration a bit too much, saying, “The disciples of John fast often and offer prayers, and so do the disciples of the Pharisees, but yours eat and drink” (Luke 5:33). 

The Pharisees had no use for John the Baptist, but because he was popular with the people, they tried to play him against Jesus. That is what unscrupulous people do: they reject someone yet still name-drop that person for their own purposes. In this case, they zeroed in on the practice of fasting. The Greek tense here indicates that Jesus’ disciples kept on eating and drinking—not just at this particular celebration, but continually. Therefore, they accused Jesus’ disciples of never fasting, as if they were simply ignoring this important spiritual discipline.

Under Old Testament law, specific times were set apart for fasting.^[1] When the religious sect known as the Pharisees emerged during the intertestamental period, they took that law and effectively “turbo-charged” it, adding more than six hundred additional rules for the Jewish people to follow, many of them related to fasting. It reminds me of something one of my seminary professors used to say, “If a little is good, a little more is better, and too much is just right.” That saying captures the Pharisees’ approach to religious practices.

The Pharisees added these laws because they believed that adhering to a list of do’s and don’ts could make a person righteous. Their religious system was a man-centered, works-based approach to having a relationship with God, and those works included additional fasting requirements. In fact, if you identified with the Pharisees, you were expected to fast every Monday and Thursday.^[2] 

Perhaps Levi’s dinner party took place on a Monday or a Thursday, which would have  heightened the Pharisees’ irritation. Their accusation was essentially this: John’s disciples fast, the disciples of the Pharisees fast, but Jesus, your disciples are continually eating and enjoying their drink. 

Jesus would address the Pharisees’ hypocritical comparison with John later.^[3] For the moment, however, he went straight to the heart of the issue, saying, “Can you make wedding guests fast while the bridegroom is with them? The days will come when the bridegroom is taken away from them, and then they will fast in those days” (Luke 5:34–35). 

A typical Jewish wedding celebration lasted seven days—it was quite the party, with a full week of eating, dancing, drinking, and rejoicing. The first miracle of Jesus recorded in the Gospel of John took place at such a wedding. When the hosts ran out of wine, Jesus miraculously turned water into wine. (John 2:1–11). Fasting at a wedding celebration would have been unthinkable. In the same way, it was unthinkable for Jesus’ disciples to fast while the Bridegroom was with them.^[4] One day Jesus would no longer be physically present, and there would be time to fast then (I will consider the biblical purpose of fasting in the Weekend Recharge). 

Jesus was God’s Anointed One, the Messiah, ushering in a new covenant relationship. Over time, many of the Pharisees had turned the Old Testament law—the commands God gave to Israel— into a system of legalism that prioritized rule-keeping over having a genuine relationship with God. Jesus came to establish a new covenant centered on grace: the free gift of salvation through his death and resurrection. This was not a rejection of the Old Testament but the fulfillment of what it had been pointing toward all along. The Law, the prophets and God’s promises were all preparing the way for the coming of God’s Son and the salvation he would accomplish.

To drive home this new way of thinking, Jesus told a parable about mending a garment and about old wineskins. He said, “No one tears a piece from a new garment and puts it on an old garment. If he does, he will tear the new, and the piece from the new will not match the old” (Luke 5:36). If you sew a new, unshrunk patch onto an old garment, what will happen the first time it is washed? The new patch will shrink and leave an even bigger hole than before. The lesson is clear: what Jesus brings cannot simply be added onto the old way. He makes those who follow him a “new creation” (2 Cor. 5:17), and one day he will make all things new (Rev. 21:5). 

Jesus expanded his lesson with an illustration about wineskins: “And no one puts new wine into old wineskins. If he does, the new wine will burst the skins and it will be spilled, and the skins will be destroyed. But new wine must be put into fresh wineskins” (Luke 5:37–38). Wineskins were made from the hides of goats or sheep and fashioned into leakproof bags. Because wine expands as it ferments, an old wineskin filled with new wine would eventually burst. A new wineskin, however, still had enough elasticity to stretch with the fermenting wine. In the same way, the old ways of the law could not contain the new covenant Jesus brought (Jer. 31:31–34; Ezek. 36:22–28); the long-awaited new covenant could not be squeezed into the old system of legalism. 

But the Jews had been drinking the “old wine” for so long and had built a religious system around the old ways that they resisted the change Jesus was bringing. He confronted their unwillingness to embrace the new covenant when he said, “And no one after drinking old wine desires new, for he says, ‘The old is good’” (Luke 5:39). 

So it is today: a new life in Christ cannot be squeezed into our old way of living; the two are simply not compatible. Jesus entered the human race as a radical—how could God in the flesh be anything else?! He offers a new way of thinking, a new way of approaching God, a new way of knowing God. When you know Jesus, the old is gone and the new has come. 

PERSONAL TIME WITH GOD
Read and reflect on Luke 5:27–32. What "old wineskins" of self-reliance, religious performance, or familiar habits might Jesus be asking you to leave behind so you can fully follow him?

Talking to God: Ask God to point out your “old wineskin” way of thinking. 

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