John the Baptist was in prison. He figured it would happen eventually. You bring the prophetic thunder down on a thin-skinned despot enough, he’s going to toss you in jail. It didn’t stop John from continuing to call out Herod. But he also had lots of time on his hands to think and he wondered about his cousin. Was he really the One?
John’s disciples would come periodically with what Jesus was up to. The stories were incredible, but also sometimes confusing. Sure there were the miracles, but there was also the interactions with the centurions and tax collectors. Jesus’ disciples didn’t exactly seem to fit the fasting and praying aesthetic of John’s disciples. And, again, John was in prison. The imprisonment had to tug at him and make him ask questions. So John sent his followers to ask the big question: “Are you the one who is to come, or should we expect someone else?”
It was a blunt question, which fit John perfectly like a camel-hair suit. One likes to think that Jesus chuckled at his cousin’s brassiness. Then he gave a non-straightforward answer, which fit Jesus perfectly. He told the Baptist’s buddies to tell John what they had seen and heard: “The blind receive sight, the lame walk, those who have leprosy are cleansed, the deaf hear, the dead are raised, and the good news is proclaimed to the poor.” Then he added, “Blessed is anyone who does not stumble on account of me.”