What the Thief on the Cross Can Teach Us

By Joseph D'Hippolito Published on April 9, 2023

Throughout Holy Week, Christians across the theological spectrum focus on Jesus’ trial, scourging, death and resurrection. In the process, many quickly pass over a brief exchange between Jesus and a fellow condemned man crucified at his side. Yet that exchange contains a subtle power that forces Christians to contemplate what really matters.

Many know about that conversation between Jesus and one of the thieves, who defends Him from another condemned criminal’s mocking and asks Him to “remember me when you come into Your Kingdom.”

Many know how Jesus responded: “I assure you, today you will be with Me in paradise.”

But that simple conversation challenges the average American Christian’s attitude toward the faith. That attitude, all too often, becomes defined by theological rivalries, clutter disguised as activity and a fear of personal inadequacy that generates constant self-criticism.

He Said I Can Come”

The Rev. Alistair Begg, pastor of Parkside Church in Cleveland and host of the radio program Truth for Life,” humorously challenged his congregation in a sermon that featured an imaginary conversation between the saved thief and an angel.

“What are you doing here?” the angel asks. “I don’t know,” the thief replies. “What do you mean you don’t know?!?,” the angel responds.

The angel stutters before calling his supervisor, who begins to ask the sanctified thief questions.

“‘First, are you clear on the doctrine of justification by faith?'” the supervising angel asks in Begg’s story. “The (thief) said, ‘I’ve never heard of it in my life.'”

The supervisor continues. “‘What about…let’s just go to the doctrine of Scripture immediately,'” he says in Begg’s story. “The guy’s just staring,” Begg says about the thief.

Exasperated, the supervising angel finally asks, ” ‘On what basis are you here?’ ” The thief provides the ultimate answer.

“‘The man on the middle cross said I can come.'”

He. Is. Beyond. Adequate

Pastor Colin Smith, pastor of the Orchard Evangelical Free Church in Metropolitan Chicago, took a more comprehensive approach. Smith, host of the radio program Open the Bible, wrote a book focusing entirely on the thief’s impressions, thoughts and emotions. That book, Heaven, How I Got Here, came out in 2015.

“I was Jesus’ last companion on Earth and his first companion in Heaven,” Smith’s thief says. “My story is unusual to say the least. But it teaches something that everyone needs to know. Entrance into Heaven does not depend on your performance in the Christian life.

“Think about what happened to me: I trusted Christ and went to Heaven on the same day. I missed out on the entire Christian life. I had no battles with temptation and no struggles with prayer. I never had the opportunity to be baptized, to receive communion, to join a church, to make a donation or to serve in a ministry.”

More importantly, Smith’s thief had no chance to change his previous behavior.

“I was in no position to do good works with my feet nailed to a wooden beam,” he says. “I could hardly walk paths of righteousness and with death hours away, there was no time for me to turn over a new leaf and live a better life.”

Yet many Christians fail to realize the implications of his final moments for their own lives.

“Since I’ve been here in Heaven, I’ve learned that many people on Earth believe that their entrance into Heaven depends on living a good and godly life,” the thief says. “They may believe that Jesus forgives but deep down, they feel that their progress in the Christian life is the key that will open the door of Heaven. How could that possibly be true?”

The thief then powerfully elaborates.

“He does not say, ‘I forgive you but I will be watching you very carefully to see how you do from now on,’ ” he says. “He doesn’t put you on probation and say, ‘Make sure you don’t mess up again.’

“If my performance was involved, even to a small degree, I could never be sure of getting into Heaven. How could you know that you’ve ever lived a good-enough life?”

You. Can’t. Be. Good. Enough.

How many of us Christians, unlike that thief, put pressure on themselves to be “good enough”? How many, as a result, live with guilt, fear, shame, anxiety, self-criticism and self-condemnation as default responses to life?

How many of us, unlike that thief, measure their spiritual accomplishments in terms of church attendance or congregational activities? How many, unlike that thief, view other Christians solely through their own theological or denominational lenses?

How many of us really incorporate the uninhibited forgiveness Jesus offers into our own lives? How many truly view ourselves as the adopted sons and daughters of God that Jesus died for us to become?

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If we don’t incorporate that uninhibited forgiveness for ourselves, how can we forgive others? If we don’t see ourselves as God’s adopted sons and daughters through His Son, how can we see other Christians that way?

All too often, the religious environments in which many Christians grow up reinforce destructive responses in a misguided attempt to enforce conduct rather than encourage freedom guided by divine wisdom.

That statement doesn’t disparage the legitimate theological differences and personal struggles every believer faces. But the thief on the cross reminds us that in the midst of those struggles, freedom is our divinely ordained birthright.

Ironically, while enduring his agonizing final hours bound to a cross, the thief found that freedom.


Joseph D’Hippolito has written commentaries for such outlets as the Jerusalem Post, the American Thinker and Front Page Magazine. He works as a free-lance writer.

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