The Pharisees criticized Jesus' conduct in the previous pericope. Now John's disciples criticized the conduct of Jesus' disciples and, by implication, Jesus.
9:14 The people who questioned Jesus here were disciples of John the Baptist who had not left John to follow Jesus. They, as well as the Pharisees, observed the regular fasts that the Mosaic Law did not require. During the Exile and subsequently the Jews had made several of these fasts customary. The Pharisees even fasted twice a week.
9:15 Jesus responded with three illustrations. John the Baptist had described himself as the "best man"and Jesus as the "groom"(John 3:29). Jesus extended John's figure and described His disciples as the friends of the groom. They were so joyful that they could not fast because they were with Him.
The Old Testament used the groom figure to describe God (Ps. 45; Isa. 54:5-6; 62:4-5; Hos. 2:16-20). The Jews also used it of Messiah's coming and the messianic banquet (22:2; 25:1; 2 Cor. 11:2; Eph. 5:23-32; Rev. 19:7, 9; 21:2). When Jesus applied this figure to Himself, He was claiming to be the Messiah, and He was claiming that the kingdom banquet was imminent.
When Jesus returned to heaven following His ascension, His friends did indeed fast (Acts 13:3; 14:23; 27:9).
9:16-17 The meaning of the second illustration is clear enough (v. 16). The third may need some comment (v. 17). Old wine containers made out of animal skins eventually became hard and brittle. New wine that continued to expand as it fermented would burst the inflexible old wineskins. New wineskins were still elastic enough to stretch with the expanding new wine.
The point of these two illustrations was that Jesus could not patch or pour His new ministry into old Judaism. The Greek word translated "old"(vv. 16, 17) is palaiosand means not only old but worn out by use. Judaism had become inflexible due to the accumulation of centuries of non-biblical traditions. Jesus was going to bring in a kingdom that did not fit the preconceptions of most of His contemporaries. They misunderstood and misapplied the Old Testament and particularly the messianic and kingdom prophecies. Jesus' ministry did not fit into the traditional ideas of Judaism. Moreover it was wrong to expect that His disciples would fit into these molds.
The old garment and the old wineskins represent Judaism as it had become encrusted with non-biblical interpretations and traditions. It did not fit the kingdom that the Old Testament predicted. Jesus used two different Greek words for "new"in verse 17. Neosmeans recent in time, and kainosmeans a new kind. The messianic kingdom would be new both in time and in kind.
In the second and third illustrations, which advance the revelation of the first, the old cloth and wineskins perish. Jesus' kingdom would terminate Judaism that had served its purpose.
John the Baptist belonged to the old order. His disciples, therefore, should have left him and joined the Groom. Unless they did they would not participate in the kingdom (cf. Acts 19:1-7).
"In his characteristic style Matthew here hints that another new age will be brought in if the kingdom comes or not. This may be the first intimation of the church age in Matthew's Gospel."414
The point of this incident in Matthew's story seems to be that disciples of Jesus need to recognize that following Him will involve new methods of serving God. The old Jewish forms passed away with the coming of Jesus, and His disciples now serve under a new covenant with new structures and styles of ministry, compared to the old order.
