The passage isn't preached very often. Indeed it is not one you use to grow your church with by any means. In fact, if you DO cover this story be prepared to have a bit more seating in your church the next week. Because I have no fear of "attendance", today's post will cover an event that is mentioned in all four gospels to varying degrees of detail. However, the lesson it holds flies in the face of much popular "Christian" reasoning.
John the Baptist was a man set apart for the gospel. His existence was prophesied in the Old Testament which foretold a "voice of one crying in the wilderness: 'Prepare the way of the Lord, make His path's straight.'" (Isaiah 40:3-5)

Shortly after he baptized Jesus, he was thrown in jail by Herod for speaking out against Herod's adultery with Herod's brother's wife. The long dark days and nights in those cells did a number on John's steadfast faith, and he began to have doubts. Being the good spiritual leader that he was, he doubted his doubts instead of giving into them, and he sent a couple of his disciples to Jesus to ask him if "he is the one who is to come, or if they should expect another." (Luke 7:20) Jesus responds by using several prophecies from Isaiah about the coming Messiah. "The blind receive sight, the lame walk, lepers are cleansed, the deaf hear, the dead are raised up, the poor have good news preached to them, and blessed is the one who is not offended by me." (Luke 7:22-23) The first thing we should learn from this is that sometimes having doubts while we walk with God is okay. If the greatest man in history had doubts, it's only logical that we can too. Jesus certainly did not scold him. The second lesson is much tougher.
The list that Jesus gives them to recite back to John has a glaring and prophetic omission in it. Jesus purposely leaves out one of the Isaiah prophecies, "and the imprisoned go free." John was in the darkest moment of his life, a miracle life that had been completely devoted to the Lord, and he wasn't going to get out of his situation alive. A little while after receiving Jesus' answer, he was dragged out of the prison and up to a party room where he was publicly beheaded as a drunken gift from Herod to his daughter-in-law. In this life, following Jesus did not work out well for him. Prosperity gospel preachers (in particular) will NEVER touch this passage, and this isn't the only one they'll steer clear of. The bible never promises that all will go well for you in this life if you follow its advice. In fact, it doesn't take more than a skim reading of Paul to realize that he does everything but promise the opposite. You WILL have a hard time in this life if you truly give it to Christ.

To answer my own questions, its a heart issue. We still don't believe that we have wicked hearts. Ultimately we don't believe that we all deserve Hell. We don't believe that God, in His mercy, is offering us a way out of our unpayable debt. We seem to think that we're mostly good people, and we're doing God some sort of favor by responding to His message of salvation. Therefore, since we're being gracious enough to give our lives to God, it's expected that He should be so kind as to give us what we think will make us happy. Here's the truth: He doesn't need you. He doesn't need me. He has every right to do whatever He wishes to any of us at any point in time for He is sovereign and He is just. You're not here to live in "health, wealth, and happiness," you're here to glorify God with every breath. Luckily though, that's what will ultimately give us the most fulfillment and joy throughout the course of our lives and beyond. He has our eternal well-being in mind. Often times, we just can't see the bigger picture.
"Pick up your cross, and follow Me." - Jesus
It is difficult to accept the idea that we should actually look forward to suffering as it says in Peter. But through suffering we grow closer to God, which is ultimately what we should all be working towards. I really like that you encourage to "see the bigger picture." It's not easy, but it's true. Well said.
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