We get this comforting idea that if we follow the Messiah life will somehow be smoother, or at least all fit together in some "good" way. Then we run smack into the reality that the only guarantee Jesus made to us had to do with the activities that come after this life. In fact, Jesus very clearly expected that his followers would have a harder time getting through this life than those who walked away. But we still have these expectations of a "Savior" and when Jesus doesn't meet them we begin to wonder if he is really who we thought he was. There are thousands of empty church pews that used to be full of people who believed in Jesus Christ. But then he didn't live up to their expectations and they went home. Their families still fought, they still had some frightening decisions to make, and they still couldn't make ends meet on a budget. They began to wonder if they had made a mistake with Jesus.
Maybe that's what happened to John. He said that he had come to baptize with water, and that the one following him would baptize with "fire from heaven." So where was the fire? So far there wasn't even smoke. So far, the Pharisees and Sadducees were still in charge of the faith, and Rome was still in charge of the government. In fact, instead of bringing in the kingdom, Jesus had kept pretty quiet up north while John got himself arrested and thrown into one of Herod's dungeons on a mountaintop down by the Dead Sea. That might make a person ask some questions. Is this any way for a Messiah to behave?
At least I hope that's what happened with John. If John the Baptist, as high up as he ranked, still had some questions, maybe there is room for me and mine.