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In response to the query on why Jesus' disciples did not fast like those of John the Baptist, Jesus tells the parable of New Wine in Old Wineskins in the Gospels viz. Matthew 9:14–17, Mark 2:21–22, and Luke 5:33–39.

Interestingly, Luke adds a verse in 5:39:

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

Of course, Jesus was not against fasting, as we hear him saying in Mt 17:21 (KJV):

Howbeit this kind goeth not out but by prayer and fasting.

He may have, however, been opposed to looking at fasting as a goal in itself. Lk 5:39, it appears, is his way of saying that people were happy clinging to the age-old traditions, like one's preferring old wine to the new. But unfortunately, the Gospels do not elaborate the connection of fasting with the analogy of old and new wine.

My question therefore, is: What is the special relevance of Luke 5:39 in the context of Parable of the Wineskins? Inputs from any denomination are welcome.

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The key to this passage is found in Matthew 9:15, Mark 2:19-20, and Luke 5:34-35:

Can ye make the children of the bridechamber fast, while the bridegroom is with them?  But the days will come, when the bridegroom shall be taken away from them, and then shall they fast in those days.

John the Baptist's disciples and the disciples of the Pharisees did not have the bridegroom. John came to prepare the way for the Messiah and those disciples of his who did not recognize Jesus through John's teaching and change allegiance (as did Andrew in [John 1:35-41][1]) were still drinking "old wine". The disciples of the Pharisees were in an even worse position as they were being actively taught to reject Jesus as the Christ and they were drinking "old wine" as well.

Although fasting (in particular) is in view here, the 'old wine' versus 'new wine' dichotomy is describing the totality of religious activity under two covenants. Since fasting is strongly related to mourning and, since this mourning is ultimately sourced in man's separation from God, it is not surprising that Jesus disciples could not fast in His presence ... God was with them! A time was coming when His immediate presence would be removed and mourning and fasting would begin again for a time. Ultimately, though, mourning and fasting will cease when Jesus returns.

Those who have become accustomed to old covenant activity (old wine) are not immediately interested in abandoning that old covenant in favor of a new covenant (new wine). Notice how Luke says, "No man also having drunk old wine straightway desireth new". Often, a mix of the two is sought in order to retain the comfort of the old and access the blessing of the new. Jesus says that this practice ruins both:

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. But new wine must be put into new bottles; and both are preserved. - Luke 5:37-38

The apostle Paul has a lot to say about those who intend and attempt to bring Jesus' disciples back under the the old covenant, those who want to put the new wine of the Spirit into the old wineskin of Law:

For there are many unruly and vain talkers and deceivers, specially they of the circumcision: Whose mouths must be stopped, who subvert whole houses, teaching things which they ought not, for filthy lucre's sake. - Titus 1:10-11

And he sternly warns the Church not to leave the Gospel and return to the Law:

O foolish Galatians, who hath bewitched you, that ye should not obey the truth, before whose eyes Jesus Christ hath been evidently set forth, crucified among you?  This only would I learn of you, Received ye the Spirit by the works of the law, or by the hearing of faith? Are ye so foolish? having begun in the Spirit, are ye now made perfect by the flesh? - Galatians 3:1-3

In order to see and enter the Kingdom one must be born again, born from above, born of the Spirit of God and to return to the bondage of the Law is to fall from grace:

Stand fast therefore in the liberty wherewith Christ hath made us free, and be not entangled again with the yoke of bondage. Behold, I Paul say unto you, that if ye be circumcised, Christ shall profit you nothing. For I testify again to every man that is circumcised, that he is a debtor to do the whole law. Christ is become of no effect unto you, whosoever of you are justified by the law; ye are fallen from grace. - Galatians 5:1-4

There are religious edifices constructed by the minds and efforts of men which talk of grace all the while yoking men into bondage to the Law:

Wherefore if ye be dead with Christ from the rudiments of the world, why, as though living in the world, are ye subject to ordinances, (Touch not; taste not; handle not;  Which all are to perish with the using;) after the commandments and doctrines of men?  Which things have indeed a shew of wisdom in will worship, and humility, and neglecting of the body; not in any honour to the satisfying of the flesh. - Colossians 2:20-23

Beware of all who say that something must be added to what Christ has done or who say that some religious activities must be undertaken in order to access or to maintain what Christ has provided. These are patching old garments with new cloth, putting new wine into old bottles; they are vain talkers and deceivers separated from the grace of God.

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What is the special relevance of Luke 5:39 in the context of Parable of the Wineskins?

In LK 5:36-39, "old" is a metaphor; i.e., a figure of speech, for the Hebrew Tanakh (aka: Old Testament), and "new" to Jesus' teachings.

The phrase ουδεις πιων παλαιον in LK 5:39 is a cloaked reference to the teachings of Judaism that Jesus likely expressed in parabolic form to prevent the scribes, Pharisees, or other pro-Judaism onlookers from wanting to kill him on the spot.

“The prejudiced person will not even try the new, or admit that it has any merits. He knows that the old is pleasant, and suits him; and that is enough; he is not going to change” (Plummer). This is Christ’s picture of the reactionary Pharisees. ~A. T. Robertson, Southern Baptist preacher and biblical scholar (d. 1934), citing Alfred Plummer, English theologian (d. 1926) at LK 5;39.

It is an expression ... towards the inveterate prejudices engendered by custom and system ... for which [Jesus] offers [against] the deep-rooted human tendency to prefer old habits to new [because it's] the unprogressive spirit which relies simply on authority, precedent, and tradition, and says, 'It was good enough for my father, it is good enough for me'". ~Cambridge Bible commentary on LK 5:39.

But the “new wine” seems plainly to be the [spiritual] freedom [from Judaism] which Christ was introducing ... men long accustomed to ["old" Judaism] could not be expected ... to take a liking for the ["new" teachings of Jesus]". ~Jamieson, Fausset and Brown, A Commentary, Critical and Explanatory, on the Old and New Testaments (aka: JFB Commentary, 1871) at LK 5:39.

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I would agree with the OP’s view that the preference for old wine is analogous to how “people were happy clinging to the age-old traditions.” Reading the commentary by Jamieson-Faucet-Brown on Lk 5:39, I disagree with this observation:

“The new wine will itself in time become old, and so acquire all the added charms of antiquity.” – Jamieson-Faucet-Brown commentary, biblehub.com

This comment takes the analogy too far. The wine here is defined by its newness. It will never become old, as though Jesus were establishing new customs and traditions that would themselves become old with time. The new wine is the wine of the Spirit (cf Acts 2:13), and the analogy of the two wines reflects the contrast between religion that is defined by rigid adherence to traditional practices and ways of thinking to one that is open and responsive to the ever new and ever evolving inspirations of the Spirit (cf Is 43:19).

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Fasting, as commanded by God, began from the Day of Atonement (Leviticus 16:29-31; 23:26-32), a day for the Israelites to observe their repentance, forgiveness and reconciliation with God. There is a contrast when Isaiah wrote

9 In that day they will say, “Surely this is our God; we trusted in him, and he saved us. This is the Lord, we trusted in him; let us rejoice and be glad in his salvation.” (Isaiah 25:9 NIV)

Isaiah prophesy was fulfilled in Jesus' presence. Jesus replied the Pharisee why His disciples did not need to fast;

15 Jesus answered, “How can the guests of the bridegroom mourn while he is with them? The time will come when the bridegroom will be taken from them; then they will fast.

The Pharisees had to continuous fasting for they did not see the Lord Jesus was their God, their salvation. Luke wrote "And no one after drinking old wine wants the new, for they say, ‘The old is better'" (5:39 NIV), indicate the spiritual blindness of the people who hold fast to the Mosaic law. They did not see a new era is beginning. It is a new covenant fulfilled in Jesus.

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