What does Luke 7:26 mean?

Jesus is addressing a mixed crowd of people. Some heard and accepted John the Baptist's message; others rejected his call to repentance because they would lose too much influence in society. Jesus designs His third question to lead the crowd into understanding who John the Baptist is. He has already asked if they came to see reeds so fragile the wind can shake them, or a man dressed in fine clothes (Luke 7:24–25). Now, He reveals the answer.

John was born about four hundred years after Malachi, the last of the Old Testament prophets. Although we have Intertestamental books, like the Maccabees, no inspired Scripture was written between the book of Malachi and the New Testament. And although God seems to have, on rare occasion, spoken to the priests, like John's father Zechariah (Luke 1:8–23), John was the first to be truly called as a prophet since Malachi.

But John is not an ordinary Old Testament-era prophet. He is the promised prophet who speaks with the spirit of Elijah (Luke 1:17). He is the one Malachi promised who would herald the Messiah (Luke 7:27). Because of his role, John is the greatest prophet who ever lived. He is the bridge between the Jewish prophets and the coming of the Holy Spirit.

Even though John is in prison, Jesus' audience knows John and has heard him speak. Many of them—the sinners and tax collectors—received his baptism and repented of their sins. Others, such as the Pharisees, rejected him and his message (Luke 7:29–30).