Q – In Luke 5:33-39, Jesus offers the wineskins parable when asked about fasting. As hard as I strain to understand this parable, I feel I’m missing something – or wind up craving a really mellow Cabernet! 🙂

What is He saying in this passage?

Jim – Let’s start by looking at the passage, starting with the banquet at Levi’s house –

“After these things He (Jesus) went out and saw a tax collector named Levi, sitting at the tax office. And He said to him, “Follow Me.” So he left all, rose up, and followed Him. Then Levi gave Him a great feast in his own house. And there were a great number of tax collectors and others who sat down with them. And their scribes and the Pharisees complained against His disciples, saying, “Why do You eat and drink with tax collectors and sinners?”

Jesus answered and said to them, “Those who are well have no need of a physician, but those who are sick. I have not come to call the righteous, but sinners, to repentance.”

Then they said to Him, “Why do the disciples of John fast often and make prayers, and likewise those of the Pharisees, but Yours eat and drink?”

And He said to them, “Can you make the friends of the bridegroom fast while the bridegroom is with them? But the days will come when the bridegroom will be taken away from them; then they will fast in those days.”

Then He spoke a parable to them: “No one puts a piece from a new garment on an old one; otherwise the new makes a tear, and also the piece that was taken out of the new does not match the old. And no one puts new wine into old wineskins; or else the new wine will burst the wineskins and be spilled, and the wineskins will be ruined. But new wine must be put into new wineskins, and both are preserved. And no one, having drunk old wine, immediately desires new; for he says, ‘The old is better.’ ” (Luke 5:27-39)

The quick answer is that Jesus was drawing a contrast between the Old Covenant (the Law of Moses, which demanded painstaking performance in order to achieve a level of righteousness) with the New Covenant of salvation by grace through faith.

It all started because Jesus purposely found a Jewish man who worked to collect taxes for Rome. These were despised men. They were considered turncoats against their own people. And, they were usually crooks, lining their own pockets by overcharging the people. These were certainly not the kind of people you would find religious men consorting with. But, Jesus chose to sit at a banquet with a room full of them.

Naturally, there were the local “scribes and Pharisees,” those who kept and promoted the Law of Moses, there in the midst. And, Jesus knew it. He was goading them. So, they took the bait and asked, “Why do you eat with such people?!”

A religious Jew would never touch an unclean thing or eat in the company of sinners. Yet, here was Jesus, considered by many a teacher, a rabbi, and He was eating with the dregs of society.

So, He answered, “Healthy people don’t need a doctor.” That’s right. People with no symptoms don’t seek medical help. Of course, Jesus was also implying that the Pharisees, confident in their self-righteousness, would never seek Him as a Savior. They saw no need. They felt whole and clean.

But, Jesus sat with sinners. Jesus knew their need. “I have not come to call the righteous, but sinners, to repentance.” Those who were seeking salvation by keeping the Law would be judged by the Law. That Law will crush them. But, Jesus’ ministry was one of reconciliation, grace and salvation for sinners. He came to call people who recognized their miserable estate and desperate need for a Mediator between them and God’s Holy judgment.

That’s the first part of the tale.

Unable to condemn Jesus on the basis of His first answer, they moved past His chosen company to the act of feasting. It was customary for the scribes and Pharisees to fast often, as a demonstration of their sanctified condition. So, they charged Him, “Why do the disciples of John fast often and make prayers, and likewise those of the Pharisees, but Yours eat and drink?”

Notice the way they built their argument. John the Baptist taught his followers to fast. We teach our followers to fast. But, we never seem to see your followers fasting. In fact, they seem to be feasting quite regularly. Clearly, your followers are not as holy as we are. What do you say to that?

So, Jesus responded in accordance to the custom of the day. When a wedding was about to take place – and for several days preceding the wedding – a huge feast would commence. And, the bridegroom’s fellows would feast with him until the moment that he went to call his wife.

So, Jesus responded that while He was in their midst, as the Bride of Christ was being established, He was like a bridegroom feasting with friends. But, He also predicted His death, resurrection and ascension. The day will come, He told them, when the bridegroom would leave. Then His fellows would fast.

The Pharisees were now “two for two.” So, Jesus explained things further, emphasizing the difference between their Old Covenant religion and the New Covenant that would be established in His blood.

He offered them two practical examples to explain the contrast. First, He explained that when an old piece of cloth was torn you would not patch it with new cloth. Any good seamstress would agree. The new cloth is stronger than the old; so eventually the tear will increase.

Likewise, Jesus said, you do not put new wine into an old wineskin. A wineskin was a leather pouch that was capable of expanding as the wine fermented – but only once. If you put new wine in an old wineskin that has already been stretched, it will burst the wineskin and then both are ruined.

So, new cloth goes into new clothing and new wine goes into new wineskins. New cloth in old clothing and new wine in old wineskins simply doesn’t work.

So, in that context, Jesus was saying that those Pharisees who were devoted to the Old Covenant practices were never going to understand the practices of the New Covenant. But, it was not meant for them. The New Covenant required new vessels and new material. That’s why Jesus chose fishermen, tax collectors and zealots to carry His message. The “old guard” of Judaism was never going to embrace it. They were old cloth and old wineskins.

And they were zealous for their religion. Having drunk themselves full of the old wine they would pronounce its superiority, “The old is better!”

So, Jesus knew their hearts and knew that they would not – indeed they could not – embrace the New Covenant. So, He turned to new cloth and new skin.

I hope that helps!

Yours in Him

Jim Mc.