The account of the two thieves on the cross is one of the clearest pictures in Scripture of how identical circumstances can produce opposite responses to Jesus. Side-by-side, they saw the same Savior, heard the same words, endured the same suffering, and faced the same urgency—yet one hardened his heart while the other repented and believed. Their final moments preach a timeless message: what ultimately separates people is not their situation, but their response to Christ.

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Table of contentsLesson 1: Jesus’ parables teach that identical circumstances can produce opposite responsesThe parable of the two buildersThe parable of the sowerThe parable of the two sonsThe parable of the ten virginsThe parable of the talents (and minas)The wedding feast, the two debtors, and moreLesson 2: The two criminals are a living illustration of Jesus’ parablesLesson 3: Each person is responsible for their response to ChristHe believes in life after deathHe believes Jesus has a kingdom beyond deathHe believes salvation is mercy, not meritHe believes Jesus will receive himJesus’ response: assurance, immediacy, and fellowshipCertaintyImmediacyPersonal fellowshipThe gospel in living colorThe “deathbed conversion” question—and Matthew 20Lesson 4: God’s grace to others can expose envy in our heartsDon’t presume on tomorrowConclusion

Lesson 1: Jesus’ parables teach that identical circumstances can produce opposite responses

Jesus regularly taught in a way that removes that excuse. He often described people who shared identical circumstances—and yet experienced opposite outcomes. Once you notice this pattern, you start seeing it everywhere in Jesus’ teaching.

The parable of the two builders

Both men heard the same teaching:

“Everyone who hears these words of mine…” (Matthew 7:24)

“Everyone who hears these words of mine…” (Matthew 7:26)

Both men built a house. Both faced the same storm:

“The rain fell, and the floods came, and the winds blew and beat on that house…” (Matthew 7:25)

“The rain fell, and the floods came, and the winds blew and beat against that house…” (Matthew 7:27)

Same teaching. Same project. Same storm. Completely different results.

The parable of the sower

There is one Sower. The seed is good. The seed is distributed broadly. Same Sower. Same seed. Same method. Yet radically different responses.

The parable of the two sons

Same father. Same command:

“Son, go and work in the vineyard today.” (Matthew 21:28)

Completely different responses.

The parable of the ten virgins

Same wedding. Same role. Same expectation: wait for the bridegroom. But two very different endings.

The parable of the talents (and minas)

Same master. Same stewardship principle. Same assignment: be faithful with what you’ve been entrusted. But again: different responses—and different outcomes.

The wedding feast, the two debtors, and more

Same King. Same invitation. Same mercy. Same opportunity. Yet not everyone responds the same. And if we’ll allow Jesus’ parables to do their work, they press us toward a sobering conclusion: the decisive issue is not the sameness of circumstances, but the posture of the heart.

That prepares us for what happens at the cross.

Lesson 2: The two criminals are a living illustration of Jesus’ parables

In recent sermons, we’ve been noticing living illustrations in Scripture:

Barabbas as a living illustration of substitutionary atonement (Jesus takes the punishment another deserved).

Simon of Cyrene is a living illustration of cross-bearing discipleship (he literally picks up the cross and follows).

Now we come to another living illustration—one of the clearest in all the Gospels. The two criminals crucified next to Jesus face nearly identical circumstances, yet they respond in opposite ways.

Here’s how similar their situations are:

Same guilt and sentence: both are criminals being executed by Rome—publicly shamed and justly condemned.

Same suffering and helplessness: neither can come down, fix their life, or perform works to “make up for it.”

Same proximity to Jesus: both are close enough to see Him, hear Him, and observe His restraint and mercy.

Same evidence: they watch the same mocking crowd, the same religious scorn, the same soldiers, the same injustice.

Same limited time: there is no future. No long discipleship process. Eternity is immediate.

Same social pressure: the whole atmosphere pushes them toward scoffing and unbelief.

Same claims about Christ: they hear “He is the Christ,” and they see the inscription, “King of the Jews.”

Same setting. Same opportunity. Same Savior. But two radically different responses.

Lesson 3: Each person is responsible for their response to Christ

Luke records the first man’s response:

“One of the criminals who were hanged railed at him, saying, ‘Are you not the Christ? Save yourself and us!’” (Luke 23:39)

His response is hardened unbelief:

He blends in with the mockers.

He shows no fear of God.

He makes no confession of sin.

He wants to use Jesus for relief from consequences—not rescue from sin.

Then Luke shows us the other criminal:

“But the other rebuked him, saying, ‘Do you not fear God, since you are under the same sentence of condemnation? And we indeed justly, for we are receiving the due reward of our deeds; but this man has done nothing wrong.’” (Luke 23:40–41)

In that statement, the second criminal does multiple commendable things:

He rebukes blasphemy because he is offended for Christ.

He demonstrates the fear of God.

He confesses guilt and acknowledges deserved judgment.

He proclaims Jesus’ innocence—even while everyone else is mocking Him.

And then we arrive at one of the simplest—and most effective—prayers in the Bible:

“And he said, ‘Jesus, remember me when you come into your kingdom.’” (Luke 23:42)

So much is packed into this one sentence.

He believes in life after death

That might sound obvious to modern ears, but it wasn’t universal in Jesus’ day. The Sadducees—prominent religious leaders—denied the resurrection.

He believes Jesus has a kingdom beyond death

He says, “Your kingdom.” At the moment when Jesus appears weakest—bleeding, mocked, dying—this man believes Christ will reign.

He believes salvation is mercy, not merit

He doesn’t bargain. He doesn’t promise to “try harder.” He doesn’t talk about making up for his sins. He simply casts himself on Jesus.

He believes Jesus will receive him

He asks because he believes Jesus is gracious.

One man suffers and uses it as an excuse to curse Christ.

The other man suffers and allows it to produce repentance and faith.

Same cross-shaped suffering. Different heart posture. And the two criminals become representative of every person who has ever lived: we will respond to Jesus with hardened unbelief—or repentant faith.

Jesus’ response: assurance, immediacy, and fellowship

Now look at how Jesus answers him:

“And he said to him, ‘Truly, I say to you, today you will be with me in paradise.’” (Luke 23:43)

Several details matter.

Certainty

Jesus begins with emphasis:

“Truly, I say to you…”

This is Jesus underlining: This is sure.

Immediacy

“Today…”

No delay. No purgatory. No working off sin.

Personal fellowship

“You will be with me…”

This is what makes heaven heaven: being with Jesus.

Philippians 1:23 — “My desire is to depart and be with Christ, for that is far better.”

John 14:3 — “And if I go and prepare a place for you, I will come again and will take you to myself, that where I am you may be also.”

Revelation 21:3 — “Behold, the dwelling place of God is with man. He will dwell with them, and they will be his people, and God himself will be with them as their God.”

The gospel in living color

This is Romans 10:13 made visible:

Romans 10:13 — “For ‘everyone who calls on the name of the Lord will be saved.’”

The thief called. He was saved.

And Jesus’ promise harmonizes perfectly with His other words:

John 6:37 — “All that the Father gives me will come to me, and whoever comes to me I will never cast out.”

He came to Christ. Christ did not cast him out.

The “deathbed conversion” question—and Matthew 20

When I became a Christian, I was raised in a works-based religion, and I had a nagging question: “What about people who live wickedly and then believe right before they die? Do they get to go to heaven like everyone else?” That question is common—especially among critics of Christianity. And the thief on the cross is the clearest biblical example: saved at the end of life, with no time left to prove anything, fix anything, or repay anything.

Interestingly, Jesus also tells a parable that addresses our instinctive complaint about “fairness”: the parable of the laborers in the vineyard (Matthew 20:1–16).

Some labor all day. Others work one hour. Yet the master pays them the same. The early workers complain—not because they were cheated, but because the master was generous. Jesus’ point is not that rewards are identical (Scripture teaches differing rewards), but that salvation is entirely grace—unearned favor.

That parable exposes what can be hiding in our hearts:

Lesson 4: God’s grace to others can expose envy in our hearts

The vineyard workers weren’t angry about what they received. They received exactly what they agreed to receive. They were angry about what someone else received.

In other words, grace offended their pride. As one commentary notes, Jesus describes this as an “evil eye”—a jealous, envious spirit that resents goodness shown to others. It’s the same issue in the older brother in the parable of the prodigal son:

“But he answered his father, ‘Look, these many years I have served you, and I never disobeyed your command, yet you never gave me a young goat,