When the messengers of John had departed (cf. Luke 7:24), Jesus immediately cleared the character of John from an unfavorable impression. Jesus implied that John was not a man swayed by public opinion (i.e., he was not "a reed shaken by the wind"). John was also not a man characterized by self-indulgence (i.e., he was not "clothed in soft garments").
The questions Jesus asked the multitude were intended to remind the people of John the baptizer's greatness. John was not a man-pleaser but firmly withstood the Pharisees. He was steadfast and fearless in rebuking Herod's sin, even when his life and liberty were at stake. Also, with his clothing of camel's hair and diet of locusts and wild honey, John stood in stark contrast with those who pampered themselves materialistically. To remind the people of these attributes of John was to rekindle their admiration for him.
Those who had gone to see John in the wilderness didn't find a man who was blown about by the opinions of men, and they didn't find a man who was concerned about personal gratification. Instead, they found one who was "more than a prophet." John the baptizer was certainly a prophet, but he was much more than that.
The prophecy recorded in Matthew 11:10 is from Malachi 3:1. John was "more than a prophet" in that he was the "messenger" who was sent before the "face" of Jesus in order to "prepare" His way. John was greater than the prophets who came before him in that they foretold the Messiah, but he was the one who announced the Lord's coming.
Matthew 11:11 teaches that true greatness arises from association and relationship with Jesus Christ. Thus, to be Christ's forerunner was to be above teacher and prophet, Levite and priest, lawgiver and king, and everyone else that the world esteems as great. John's role as Christ's forerunner is what made him the greatest of "those born of women."
However, "he who is least in the kingdom of heaven is greater than he [i.e., John]." This clearly proves: (1) that John was not in the kingdom which Christ referred to here (or else the least in the kingdom could not be greater than John) and (2) that kingdom had not yet been set up; it was still "at hand" at that point in history (Matt. 3:2; 4:17). The kingdom Jesus was referring to was not heaven, but the church. This must be the case since heaven will certainly not "suffer violence" (11:12).
The question begs to be asked: How are those who are "in the kingdom" greater than John? It is through their closer relationship with Christ! John never had the knowledge of Jesus' crucifixion and resurrection; thus, he never knew the full revelation of God's love. John was not a child of God in the same sense that Christians are today. He died before the kingdom or church came into existence on Pentecost. He did not have access to all the spiritual blessings that the least of God's children have today, simply because he was never "in Christ" (Eph. 1:3). Therefore, those who are God's faithful today enjoy an association with Christ that none of those who lived and died under the law of Moses enjoyed--not even John the baptizer. What a privilege we have been blessed with!
We will continue studying Jesus' words regarding John the baptizer tomorrow.