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Imprisoned in the Dungeon of Doubt

by Stephen Davey Scripture Reference: Matthew 11:2–19; Luke 7:18–35

Difficult circumstances and unfulfilled expectations can cause us to doubt God’s plan and purpose. They should also drive us to God’s Word, which answers our doubts with His promises.


John Bunyan was a pastor who lived in the mid-1600s in England. Because of his biblical convictions, he refused to align his church with the Church of England and was often thrown into jail for preaching as an unauthorized pastor. 

While serving time in prison, as he did on more than one occasion, he wrote several books. The most famous one, published in 1678, was The Pilgrim’s Progress. If you have not read it yet, you need to.

In this allegory, Bunyan writes about the experiences of a young believer named Christian who is traveling from his home village to the Celestial City—or heaven. His experiences along the way illustrate the trials and temptations of every Christian. But in the story John Bunyan included many of his own challenges—especially his own personal battle with doubt.

In one particular episode, Christian and his companion Hopeful are traveling through a certain field, where they rest for the night. But they are captured by a giant named Despair, who takes them to his castle, called Doubting Castle. He throws them into a dungeon cell. Over the course of several days, they are beaten by Despair, who enjoys making their lives miserable.

Finally, one night, Christian and Hopeful are praying for help, and suddenly Christian remembers that earlier in his journey he had been given a key called Promise. He takes it from his pocket, and when he slips it into the lock of their cell door, it opens. In fact, that key opens every locked door that stands in their way to freedom.

Finally, they reach the outer gate of the castle, and it opens as well. Christian and his friend Hopeful run for their lives back to the King’s Highway and on toward the Celestial City. 

John Bunyan was writing about something every honest Christian admits—a struggle at times with the giant Despair and Doubting Castle.

Even William Carey, the man we call the Father of Modern Missions, wrote this in his journal, in 1794:

I am defective in all my duties; in prayer I wander … my soul is a jungle, when it ought to be a garden; I am, perhaps, the most inconsistent [Christian]. I can scarcely tell if I have the grace of God or not.[1]

How do you respond to Despair and his Doubting Castle? Well, in this next encounter as we sail through the life of Christ on our Wisdom Journey, we find here in Luke’s Gospel that the news of Jesus’ ministry reaches an innocent man locked up in prison. His name is John the Baptist. Herod had put him into prison some eighteen months earlier.[2]

John has evidently grown disillusioned. Think of all he had expected after he had announced the Messiah’s arrival. He had preached that the golden age of God’s kingdom was just around the corner.[3] But where is the conquering King? Herod is still in power, the religious hypocrites are still influential, the Roman Empire is still in charge, and he is sitting in prison.

We are told here in Luke chapter 7 that John sends two of his disciples to find Jesus and ask Him a question—and this question is filled with sorrow and despair and doubt. They ask the Lord, in verse 19, “Are you the one who is to come, or shall we look for another?”

“Jesus, are you really the Messiah? Have we been following the true Son of God?” You might put their question this way: “Lord, if You are the one we were expecting, why isn’t anything happening that we expected?” Isn’t that what creates doubt in our hearts today? “Lord, You are doing something we were not expecting,” or “You are not doing something we expected. In fact, Lord, nothing right now is making any sense at all.”

One author wrote this:

We don’t necessarily doubt that God is love; we just doubt at times if God loves us. How can I believe He cares about me when I’ve lost my job; my spouse left me for someone else; I’ve been diagnosed with an incurable disease.[4]

I can easily say that God loves the world; I just don’t think He loves me.

Let me tell you, I am so grateful that God allowed this question to come from the lips of this great prophet because we would assume that somebody like John the Baptist would have the answers, not the questions. He would never give in to despair or doubt, and he certainly would not question Jesus.

Jesus responds here in verse 22:

“Go and tell John what you have seen and heard: the blind receive their sight, the lame walk, lepers are cleansed, and the deaf hear, the dead are raised up, the poor have good news preached to them.”

Don’t miss the point. Jesus does not say, “Go back and tell John I cannot believe he is doubting me. What do you mean, ‘Should we look for someone else?’”

Instead, Jesus quotes four different verses from Isaiah that refer to the work of the Messiah (Isaiah 26:19; 29:18; 35:5; 61:1). In effect, Jesus says, “John, remember; God’s Word says this is who I am.” Jesus then says in verse 23, “And blessed is the one who is not offended by me.”

Evidently, these quotations from Isaiah were good enough for John. While Jesus’ response did not set him free physically, it did set his mind and his heart free.

Instead of rebuking John, Jesus sets the record straight with an amazing tribute to the prophet.[5] He says in verse 28:

“I tell you, among those born of women none is greater than John. Yet the one who is least in the kingdom of God is greater than he.”

Jesus is talking about you and me as His followers. John was great, but even little you and me are more greatly blessed. How? Well, for one, we have greater blessing than John had. John died before Jesus’ ministry was complete. He did not live to see the resurrection; he did not see the church created; he never saw a complete Bible. We have all of that and more.

Jesus now turns to the crowd of unbelievers and delivers a rather pointed message:

“To what then shall I compare the people of this generation, and what are they like? They are like children sitting in the marketplace and calling to one another, ‘We played the flute for you, and you did not dance; we sang a dirge, and you did not weep.’” (verses 31-32)

In other words, they rejected the invitation of John the Baptist to weep when he sang a dirge. Likewise, they rejected Jesus’ invitation to dance when he played the flute of good news, so to speak.

The preaching themes of John and Jesus were different in many ways, but they preached the same message: Repent; the kingdom is on the way. And they were both rejected by the self-righteous religious leaders and the nation of Israel.

Beloved, this event in John’s life shows us the difference between doubt and unbelief. Doubt does not understand what God is doing; unbelievers do not care what God is doing.

So, what do you do, beloved, when you feel trapped in the prison cell there in Doubting Castle?

You escape that dungeon of despair the same way Christian did in The Pilgrim’s Progress—not by some heroic act of faith or by some inner determination to do better, but by reaching once again, in all your weakness and helplessness, for the key called Promise; that is, the promises of the Word of God.

Go to God’s Word, and claim His promises. God will keep His word. He will never break His promise to care for you, to guide you, to love you, all the way to the Celestial City of heaven.

[1] S. Pearce Carey, William Carey (The Watchman Trust, 1923), 126.

[2] We are following Luke’s account here, which is paralleled in Matthew 11.

[3] Charles R. Swindoll, Insights on Luke (Zondervan, 2012), 176.

[4] James Montgomery Boice, Romans: An Expositional Commentary, Volume 1 (Baker, 1991), 960.

[5] Bruce B. Barton, Dave Veerman, and Linda K. Taylor, Life Application Bible Commentary: Luke (Tyndale, 1997), 182.

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