Chapter 11. Matthew allows the readers to see the reality of faith, even the faith of the “super spiritual”. Faith doesn’t come without doubts and everybody has them. Even John the Baptist, Jesus own prophetic escort (v3). Perhaps the isolation of prison caused John to battle growing doubts in his own mind. Christians, even the ones who seem to know Jesus the best, tend to expect things from Him and when things do not go the way they expect, doubts rise to the surface. Perhaps John was expecting the Messiah to come and free him from prison or bear more of a role in Israel’s government as Isaiah prophesied that He would. Jesus gives John’s disciples other scriptural evidence showing how His miracles fulfill the Scriptures regarding Him. Again, Jesus settles matters of faith with the Scriptures.
Turning now to Jesus’ own followers, there is certainly now doubts in their minds as well. If John the Baptist could doubt, then certainly any one else could. Perhaps many who are following Jesus now are those who first followed John. Jesus ask them the manner of John the Baptist, the man they “went out to see”. Jesus explains John was most honored of prophets for the ministry of introducing the Savior. “The least of the kingdom is greater than he” (11:11) because the benefits of entering the kingdom are greatest men have yet seen on the earth. Remember, the kingdom of heaven is nearly a synonymous term with the Church age where men and God are reconciled and gifted with the Holy Ghost.
The kingdom of heaven receives violence because there are men who violently fight against it, thus John the Baptist finds himself in prison for the preaching of the kingdom of heaven. Such violence against the kingdom and evil men’s apparent triumph over the kingdom only bred more doubts in the disciple’s minds. So Jesus describes this “generation” as a people who piped and mourn but didn’t get the reaction they wanted out of Jesus. Is anyone innocent from not expecting God to serve us in the way we piped and mourned to Him in our prayers? We often expect God to serve us like a genie and when He doesn’t we “doubt” Him. Furthermore, the greatest antagonists of Christ seek to turn the disciples against by arguing that John is too stern and Jesus too gracious. (11:18-19) But this is an obvious contradiction of opinions that Jesus didn’t see the need to further explain. People will doubt and antagonize either way.