As we recall, John is in prison for speaking out against Herod’s sin (marrying his brother’s wife). From prison he sends disciples to speak with Jesus because despite being locked up for a year, word has still reached him of Jesus’s work. John’s purpose from God was to clear the path for the Messiah and it sure sounds like Jesus might be the guy so he just asks him directly. This may have been for strict clarification or it could’ve been indicative of his disappointment. Jews of the time were expecting an overthrow of Rome and John had foretold that Jesus would deliver judgement so the question of “…..is that happening or not” may have been on his mind. In response, Jesus tells them to report back what they’ve seen to John, namely the miracles He’s worked which are all fulfillments of Isaiah, which John would recognize. He ends by reminding (mild rebuke) John not to give up on Him just because He isn’t what John or others expect and that by holding on, they will be blessed.

“A reed shaken by the wind” would be an incredibly common and uninteresting sight to the people following John as he baptized people surrounded by that exact sight. No, no one was there for the reeds. They’re also weak plants, and John was a prophet known for a wild and strong lifestyle, very much unlike a frail plant. The comparison continues into clothing. John wore rough camel hair clothes, not soft nice robes of a king. He’s addressing a crowd of people with a desire to believe but struggling with some doubt. Doubt in Jesus and doubt in John for backing Jesus. Here He makes His point clear: they went into the wilderness to see a strong and rare prophet, not a weak/common reed and soft comfortable clothes. A prophet was no common thing to begin with and john was even more than that and Jesus cites scripture to back it up and confirm He is the messiah as well. The “Prophets and the Law” are what we call the Old Testament and John marked a shift to the coming of the new kingdom and New Testament.

“He who has ears….” is a “let the reader understand” moment. Jesus is saying “think hard about what I just said”. He’s underlining His claim to be God. He goes on to rebuke the crowds as being like children, having invented a game in their head and expecting others to follow the rules established. “Why aren’t John and especially Jesus acting the way WE want/expect?” Because God writes the rules, not us. John didn’t eat or drink so he’s wrong. Jesus DID eat and drink, so HE’S wrong. It doesn’t matter what they do, it’s always wrong because the crowd is bullheaded. He calls out cities that didn’t accept Him and didn’t repent.

What does it mean to repent? It means to change one’s mind, but Biblically it means to feel sorry for sin and modify your behavior to take you away from that sin and towards improvement. It’s not enough to feel bad, you must seek betterment. So when you see someone tell someone else to repent, that’s not simply a command to stop and pray for forgiveness, it’s to “sin no more”. “Woe” is used in the New Testament to convey both sorrow and judgement. As in, fire is coming for you and yeah that sucks man.

Jesus declares thanks to the Father that He’s hidden things from the wise and revealed them to children. This is to say that smart people can delude themselves into stupidity and children, more a blank slate, can just affirm the things in front of them. A modern example is an adult doing mental gymnastics to affirm a transgender and a child will just be like “look mommy, a man in a dress”. It’s obvious to the child looking with innocent and accepting eyes, but even the obvious eludes the wisest man with a heart hardened against truth. If you choose to not understand, God will help you to not understand because you have a heart issue. Jews of the era were struggling to know God. P&S’s made this much harder than it needed to be with extra rules and performances and clique behavior. The people who earnestly wanted to know God were tired. This was an enormous undertaking with a bar that was constantly raising. Jesus is here to make that path to God easy. Drop all the pretense and showmanship and rest on Jesus. Let yourself be yoked to Jesus and follow His lead.