NOTES for Mat 11:2-19
Traditionally, it is held that John did not doubt Jesus' messianic calling and sent his doubting disciples to Him so that they could see for themselves. Other interpreters allow that John himself may have doubted it. Be that as it may, it is hardly accidental that he sent two of his disciples to Jesus: they were to become witnesses to Christ's words, and under Jewish law there had to be at least two witnesses. And then they heard an answer that still puzzles some readers of the Gospel: why did Christ say neither yes nor no? Why instead did He need to speak a long phrase listing His works?
Apparently, He answered this way so as not to confuse ahead of time those who were not yet ready to hear a direct confirmation. But the verbal message that Jesus asks them to convey to John contained a list of the signs of the Messiah's coming that had been foretold in the Old Testament, and this means that Jesus was quite definitely confirming that He is the very One who was to come.
Christ gives John a high evaluation. But next to it stands the indication that the least in the Kingdom of Heaven will be greater than John. Such a definition may sound like belittlement. But anyone who, confident of his own salvation, decides on that basis to exalt himself above John will be deeply mistaken. Those who enter the Kingdom of Heaven transformed will surpass John as he was on earth. But he himself in the Kingdom of Heaven will surpass himself as he was in the earthly world.