What does Luke 7:28 mean?
Jesus finishes His explanation of the importance of John the Baptist with a cryptic description.John is the last of the Old Testament-era prophets (Luke 16:16). As such, he will share a fate common to prophets: being murdered for his message (Mark 6:17–29). Jesus, He whom John heralded, affirms John is the greatest of all prophets to that time. This is not because of personal holiness or merit, but because of his prophetic role. He is the last of the Old Testament prophets. He is the hinge between the Old and New Testaments: the Dispensation of the Law and the Dispensation of Grace. He is the forerunner of the Messiah. His prophetic work provides a transition between the promise of salvation and its fulfillment.
Greatness aside, John is also like the Old Testament prophets who did not live to see their own predictions completed. John dies before the crucifixion, the resurrection, the ascension, and Pentecost. As a prophet of the Old Testament age, he is filled with the Holy Spirit (Luke 1:15), but he is not indwelt by the Spirit (Acts 2). His natural life does not last until the inaugurated kingdom of God. He only gets to announce its coming arrival.
The kingdom is inaugurated in the days from Jesus' crucifixion to Pentecost. The indwelling of the Holy Spirit blesses Christians, makes them citizens of God's kingdom (Philippians 3:20), and seals them for salvation (Ephesians 1:13). The kingdom will not be fulfilled until Jesus' return—we are in the "now and not yet"—but it has begun. Christ-followers now are "greater" than John not because of anything we have done, but because we are blessed to live in this time.
Luke goes on to compare the reactions to John by the sinners and the Pharisees (Luke 7:29–30). The sinners and tax collectors accepted John's baptism and repented from their sins. They are "prepared" to accept Jesus (Luke 7:27) and, at Pentecost, receive the Holy Spirit. The Pharisees and scribes rejected John's message. At this point, they are not ready for the kingdom of God; they choose to stay in the time of the prophets and the Law. Jesus is saying that the vilest sinner who repents and enters the kingdom is greater than John who is greater than all the Pharisees, scribes, and priests who heard his message and rejected it.
"Born of women" is probably in comparison to those who will be born again: born of the Spirit (John 3:1–15). It is not saying that if technology develops an artificial womb, a child could be greater than John.