The reports he is getting back don’t sound anything like the Messiah he, or the rest of Israel, is expecting. John lived out in the desert and denied himself. He sacrificed to serve God. The Messiah is supposed to be overthrowing Rome and returning the power to righteous Jews. Jesus just sounds like a self-indulgent troublemaker, not their chosen redeemer.
John’s whole life has been about holy self-denial, while Jesus is out there making wine for wedding parties.
Jesus will sum up this difference well:
For John came neither eating nor drinking, and they say, ‘He has a demon.’ The Son of Man came eating and drinking, and they say, ‘Here is a glutton and a drunkard, a friend of tax collectors and sinners.’ But wisdom is proved right by her deeds.” —Matt. 11:18–19
In this comment, Jesus is pointing out how Israel finds fault with all her prophets, but another point comes shining through. Jesus is developing a terrible reputation because of the people he’s hanging out with — a reputation that’s been making its way back to John.
John has to be starting to wonder if he’s made a huge mistake. Is he sitting in prison because he threw his support behind the wrong man? Wasn’t John always faithful? Didn’t he deserve better? Wasn’t he told his whole life that he’d be significant, and an important figure in the Messiah’s story? WHAT IS GOING ON!?
John confronts Jesus
When he’s had just about enough, he sends his followers to confront Jesus.
When John, who was in prison, heard about the deeds of the Messiah, he sent his disciples to ask him, “Are you the one who is to come, or should we expect someone else?” —Matt. 11:2–3
There’s no mistaking the accusation in this inquiry. Through his disciples, John is saying, “I have endorsed you as the Messiah, and you acknowledged that role. I’m sitting in prison trusting that I didn’t make a mistake. Are you who you said you are or not? Should Israel be looking for someone else!?”
John deserves a forthright answer, but Jesus doesn’t exactly give him one.
Jesus answered and said to them, “Go and report to John what you hear and see: The blind receive sight and the lame walk, the lepers are cleansed and the deaf hear, the dead are raised up, and the poor have the gospel preached to them.” —Matt. 11:4–5
Pointing at the miraculous work that he’s doing and away from the gossip, Jesus is basically saying, “If you pay attention, you will see that I am.”
And then he says the most enigmatic, heartbreaking thing to John. He says:
“And blessed is he who does not take offense at Me.” —Matt. 11:6
“Despite all you’re being told, and the fact that you’re sitting in prison, don’t be offended at me. Don’t stumble in your faith on my account. I know you had expectations about how all of this was going to play out, and I am sorry to tell you — it’s nothing like you imagined. Trust me, and don’t let the offense of your dashed presumptions shipwreck you.”