Jesus said a partial "blindness" has happened to Israel until the time of the Gentiles is fulfilled. Partial blindness suggests you can see, just not the whole picture. It might be strange that Christians, who debated the parable of the wineskins for centuries, never bothered to ask the Jews what he meant. I mean, are we not grafted into the olive tree? When will we become the "one new man."?
Jesus grew up in the rabbinic traditions of his time. He knew how the world of Judaism worked. The scriptures even refer to him as a rabbi. So a simple proposal: the scribes and Pharisees were familiar with the parable of the wineskin.
During the time to the rabbi, students would petition their teachers to walk in the footsteps of their chosen rabbi. They would quite literally follow them around until they made the cut or sent back to the family trade. However, only the brightest and best were allowed to petition the rabbis.
Ever wonder why the Pharisees and scribes followed him around, ever bugging him about his company, yet perplexed and amazed at his word?
They heard a new Torah interpretation and knew it was powerful. They even asked him on one occasion where he received his authority. As a rabbi progressed through the echelon of Judaism, a rabbi would be allowed, on the blessings of his old rabbi, to establish his own interpretation of the Torah. As such, his disciples would follow this new Torah teaching or new wine, learning and all the ways developed by this new doctrine.
Now consider the setup of Luke 5 when the Pharisee questioned Jesus about his choice of disciples. Jesus gives a reason, justifying his selection of disciples. The disciples of John, considered by many to be a prophet, fasted and prayed often. To the eyes the of the Pharisee and scribes, they had no idea what to make of these new "wineskins" who ate and drank with sinners. It was beyond them. They preferred the old wineskins and as the gospels clearly show the old wine.
The answer to the parable comes from many Talmudic and rabbinic sources. The rabbis taught that the wine was the Torah and the vessels are the people, in this case, his choice of disciples. John' students understood the old wine in a way unique to the teachings of John. They were old wineskins. The previous understanding of the Torah would prevent them from learning what Yeshua wanted to teach them about his law. If we consider this idea then the phrase at the end of Luke 5:39 makes sense. No one, hearing the teachings of Jesus could swallow this new wine. Jesus needed fresh wineskins to carry this message.
So does this concept of wine, is it seen in the Old Testament?
Consider the following:
Binding his foal unto the vine, and his ass's colt unto the choice vine; he washed his garments in wine and his clothes in the blood of grapes
(Jesus, the true vine, who rode into Jerusalem on a donkey, and Isaiah's grape squasher)
And I have led you forty years in the wilderness: your clothes are not waxen old upon you, and thy shoe is not waxen old upon thy foot.
Ye have not eaten bread, neither have ye drunk wine or strong drink: that ye might know that I am the LORD your God.
(A reference to Israel in the wilderness, it includes the reference to garments and wine, and ironically they ate and drank "Torah")
And these bottles of wine, which we filled, were new; and, behold, they be rent: and these our garments and our shoes are become old by reason of the very long journey.
(Again, both new wine and garments)
Who is this that cometh from Edom, with dyed garments from Bozrah? This that is glorious in his apparel, traveling in the greatness of his strength? I that speak in righteousness, mighty to save.
Wherefore art thou red in thine apparel and thy garments like him that treadeth in the winefat?
I have trodden the winepress alone; and of the people, there was none with me: for I will tread them in mine anger, and trample them in my fury; and their blood shall be sprinkled upon my garments, and I will stain all my raiment.
(Notice only the Messiah is treading the winepress. Messiah makes new wine from the Torah. And fun fact, Jews consider Edom=Christianity…)
And it shall come to pass in that day, that the mountains shall drop down new wine, and the hills shall flow with milk, and all the rivers of Judah shall flow with waters, and a fountain shall come forth of the house of the LORD, and shall water the valley of Shittim.
(again, new wine)
Before we turn into old wineskins, incapable of holding Yeshua's new wine, due to denominational blindness, maybe a lesson from the Berean Jews is in order.
"Now the Bereans were more noble-minded than the Thessalonians, for they received the message with great eagerness and examined the Scriptures every day to see if these teachings were true."