Be Prepared!
And the disciples of John told him all these things, and John summoned to himself two of his disciples he sent them to the Lord saying “Are you the one who is coming or are we to look for a different one?” When the men had come to Him they said “John the Baptist sent us to you saying ‘Are you the one who is coming or are we to look for a different one?’” In that hour He had healed many with diseases and torments and evil spirits, and many blind He granted the ability to see. And He answered them saying “Go yourselves, tell John the things you saw and heard, the blind regain sight, the lame walk, the lepers are cleansed, the deaf hear, the dead roused, the poor have the good news preached for them, and blessed is the one who shall not offended by me.” When the messengers of John had gone He began to speak to the crowds concerning John “What did you go out into the wilderness to see? A reed shaken by the wind? What, then, did you go out to see? A man dressed in soft robes? Behold, the ones in fine clothing and exist in luxury in the palaces. What, then, did you go out to see? A prophet? Yes, indeed, I say to you, and greater than a prophet. This is the one about whom it has been written 'Behold I send my messenger ahead of you, who will prepare your way before you.' I say to you, no one born of women is greater than John. But the least in the kingdom of God is greater than he." Luke 7:18-28The third week of Advent is traditionally focused on joy. Hence the rosy colored vestments. But John really isn't the typical "rainbows and sunshine" preacher. Especially right now.
The last prophet, sent to prepare the hearts that had strayed from God, was in prison. And not like prisons today, or even prisons back in the 1800s. Like, a prison that makes the Bastille look like a Sandals resort.
So is it understandable that John asks is Jesus is really the Messiah? This is the guy who, while still in the womb, was jumping in excitement knowing that he was in the same room as the Savior. And he had no fear speaking truth to power. So why ask this now? Why not when Christ was at the river, being baptized?
But John's question is understandable. He knows that the end, for him, is soon, and he wants to know that he hasn't been wrong.
Paul had somewhat similar circumstances. He was in prison, multiple times. Yet, as he wrote to the church in Philippi, he expressed that, no matter what, he was content. This is because of his assurance and hope in Christ. Not that John did not have hope, but it wasn't as clear before Christ's death and resurrection. That and Paul wasn't quite under the same threat of death (at that time).
Which, in many ways, is for our benefit and joy. We can look back and be certain that Christ has died for us. And for that, we celebrate and wait for His return.