John the Baptist: The Greatest and the Least

I'm in a John the Baptist kind of mood. First, I was thinking about this passage:

² And when John had heard in prison about the works of Christ, he sent two of his disciples ³ and said to Him, “Are You the Coming One, or do we look for another?” ⁴ Jesus answered and said to them, “Go and tell John the things which you hear and see: ⁵ The blind see and the lame walk; the lepers are cleansed and the deaf hear; the dead are raised up and the poor have the gospel preached to them. (Matt. 11:2-5)

It took me a while to appreciate the timeline implied by this passage. For I always took it to mean that the two ambassadors from John arrived, and Jesus provided them a quick answer, and sent them packing. Which would not have been a very satisfying report for John to receive. But I am convinced the language supports the notion that the men were to stay for a period and observe Jesus' ministry, and only then return to reassure John with eyewitness accounts. A quick answer would only tell John that Jesus was talking the talk. A period of observation of his ministry would demonstrate that he was walking the walk as well.

John, the last prophet of the old age that was coming to an end, the Jewish age if you will, recognized (although doubts were creeping in) Jesus as the one who was to usher in the new age, the Kingdom of Heaven. However, it would appear that Jesus didn't quite initiate the new age in a manner that met John's expectations. So Jesus told John's messengers to hang around and witness the direct fulfillment of prophecy, such as

Then the eyes of the blind shall be opened, and the ears of the deaf shall be unstopped. (Isa. 35:5)

and only then report back to John, who would be reassured that Jesus was indeed the coming one, and the new age was indeed at hand. The "end of one age, start of another" theme also explains the somewhat paradoxical:

“Assuredly, I say to you, among those born of women there has not risen one greater than John the Baptist; but he who is least in the kingdom of heaven is greater than he. (Matt. 11:11)

Here "born of women" is a metaphor for those under the Old Covenant, in contrast with those in the New Covenant, born of water and Spirit (John 3:5). The least of those who are citizens of the Kingdom of Heaven, i.e. who live in the age made possible by the finished work of Christ, are "greater" in terms of their privilege, than even the greatest who livd before the onset of the Kingdom. If for no other reason than faith was in some sense harder for Old Testament saints, who had to have faith in a promise, while our faith rests on the documented (in the bible) historical events of the crucifixion and resurrection of our Lord.