When John’s disciples leave with their answer, Jesus begins teaching the crowds about John, and his role in God’s plan. He starts with the question, “What did you go out to see?” and gives some obviously wrong answers as a rhetorical device. This is to get the listeners to be introspective and think about why they were interested in hearing what this hermit in the wilderness was saying. John warned of coming judgement and of the need for repentance to avoid the wrath of God. But why did the people think he was right about it? Because he was “a prophet”, and then Jesus asserts that he was more than just any prophet, but the prophesied forerunner to the Messiah.
In verse 28, Jesus says no one born of woman is greater than John, but everyone in the kingdom of God is greater than John. Is He saying John isn’t in the kingdom of God, that he isn’t saved? No, I think He’s showing how great a difference there is between a physical birth and a spiritual rebirth. You can do all these good deeds, know a lot of truth, even have your life be predicted in Scriptures, but it doesn’t matter at all if you aren’t in God’s kingdom. The people who had been baptized by John understood what Jesus was getting at, and they agreed, because it lined up with what they had already heard from John.
The Pharisees and experts of the Law of Moses didn’t agree with this, because they were banking their spiritual future on their good works and their knowledge of the truth. They rejected both John and Jesus, so Jesus calls out their contrariness. He compares them to children who don’t want to play anything that someone else suggests. John lived an ascetic life, to an extent that he was accused of mental illness. Jesus feasted and attended parties with sinners and religious outcasts, so they called Him a glutton and a drunkard. These are the same critics, and they weren’t satisfied by anyone’s message but their own.
Let us be receptive to Your message, and not cling to our own paths, which will not bring us to You in the first place.