In Matthew 11, John the Baptist is languishing in Herod's prison, and he wonders if Jesus really is the Messiah. He sends two of his disciples to ask Jesus this question, and Jesus points him to his miracles as evidence. After John's disciples leave, Jesus then tells the crowd about John the Baptist. He says that John was not a reed shaken in the wind, nor was he clothed in dainty garments, the types you would see in palaces. Rather, John was a prophet, if not more. Actually, he was the prophesied voice in the wilderness who had prepared the way of the Lord.
I wondered why Jesus said all these things about John the Baptist, so I checked my trusty E-Sword commentaries. And, fortunately, they offered some decent, contextual interpretations. In Matthew 11:6, Jesus said, "And blessed is anyone who takes no offense at me" (NRSV). That appears to be a put-down to John. But Jesus wanted to clarify to his audience that John was actually a great man, a holy man. According to Jesus, John was not a reed shaken in the wind, that is, a man unstable in his faith and convictions. He was not someone who sought power and influence within society's upper echelons, nor did wealth "sissify" him. Rather, he was a tough, rustic figure, a wilderness man who was boldly committed to doing the will of God, even if that landed him in jail. Like the prophets of old, he was a righteous man who dared to speak truth to power.
Here is another possible reason that Jesus emphasized John's "outsider" status: Jesus was trying to prepare his audience for a different kind of kingdom. Many first century Jews expected a Messiah who would free them from the Romans and establish a Golden Age, better than the days of David and Solomon. That would involve wealth and power for Israel. But Jesus was a low-key person whose mission was to suffer. He reached out to the lowest people of society: the poor, the sick, and the outcasts. Wealth and power were the opposite of what Jesus represented.
And so, in addition to salvaging John's reputation, Jesus may be saying in Matthew 11:7-9: "Look, there was something that drew you to John the Baptist. He's not like a lot of celebrities you know. He didn't have much wealth or political power, the sorts of things you usually find attractive. But there was something about him. And I want you to get in touch with that something, because that is what my kingdom is all about. And all sorts of people are entering it by force, regardless of the opposition it's experiencing."
This is not to imply that first century Judaism focused solely on wealth and power, or looked down on the poor and the sick. We can read in rabbinic sources that the heirs of first century Judaism did not do this, for Judaism has always had a lot of positive values. But people are people, regardless of the age in which they live. People today glorify glamor, wealth, and power, even if they may give lip-service to higher ideals. So why should we assume that people back then did any differently? But Jesus was trying to reorient their perspective onto true values, such as righteousness, justice, courage, and humility. And John the Baptist was someone who exemplified these things.