Questions

1. Fill in the blanks below from Matthew 27:17-23: So when they had gathered, Pilate said to them, “Whom do you want me to release for you: ________, or Jesus who is called Christ?” ¹⁸ For he knew that it was out of ______ that they had delivered him up. ¹⁹ Besides, while he was sitting on the judgment seat, his wife sent word to him, “Have nothing to do with that ____________ man, for I have suffered much because of him today in a dream.” ²⁰ Now the chief priests and the elders persuaded the crowd to ask for Barabbas and destroy Jesus. ²¹ The governor again said to them, “Which of the two do you want me to release for you?” And they said, “Barabbas.” ²² Pilate said to them, “Then what shall I do with Jesus who is called Christ?” They all said, “Let him be __________!” ²³ And he said, “Why? What evil has he done?” But they shouted all the more, “Let him be _________!”
2. TRUE or FALSE: Pilate genuinely believed Jesus was guilty.
3. Which Scripture records Jesus weeping because people did not recognize what would bring peace?
4. Matthew 27:17
5. Luke 19:41–44
6. John 18:38
7. Romans 8:28
8. Barabbas was released instead of Jesus during the ________ prisoner release.
9. TRUE or FALSE: Pilate tried multiple times to avoid making a decision.
10. What does Pilate’s repeated declaration of Jesus’ innocence reveal most clearly?
11. Pilate’s weakness as a judge
12. Pilate’s confusion about Roman law
13. Pilate’s awareness of political manipulation
14. Pilate’s personal faith in Jesus
15. Washing his hands was Pilate’s attempt to symbolize:
16. Repentance
17. Neutrality
18. Moral innocence
19. Legal justice
20. Pilate’s wife warned him to have nothing to do with that ________ man.
21. Washing his hands symbolized Pilate’s attempt to avoid ________.

Discussion

1. To prepare to answer this series of questions you can review this section of the message in this link to the video: In his book Perilous Pursuits (Timestamp 3:52 to 12:54)
2. How does the illustration of the Porsche and scooter help us understand Pilate’s position in the trial of Jesus?
3. How might we confuse control or success with peace?
4. Why is this illustration important for framing the rest of the sermon?
5.  Discuss the following questions in this link to the video: Pilate’s Disingenuous Amnesty Program (Timestamp 12:55 to 16:10)
6. Why is Pilate’s amnesty program described as disingenuous?
7. What contrast is set up between Barabbas and Jesus?
8. How does this choice reveal the crowd’s understanding of peace?
9. How does Pilate’s strategy expose the illusion of control?
10. Put yourself in a modern situation that has pressures like Pilate faced: discuss the pressures that you might feel to go the way of the crowd for expediency vs standing for the truth.
11. To prepare to answer this series of questions you can review this section of the message in this link: Then Pilate's Wife Sends an Alarming Message (Timestamp 16:11 to 20:21)
12. Why is it significant that Pilate’s wife calls Jesus a righteous man?
13. How does this warning remove Pilate’s excuses?
14. Why doesn’t Pilate respond faithfully to this warning?
15. What does this moment teach about knowing truth versus obeying it?
16. To prepare to answer this series of questions you can review this section of the message in this link: Pilate’s Capitulation to the Pragmatics of Political Life (Timestamp 20:22 to 28:22)
17. What finally forces Pilate to condemn Jesus?
18. How does fear shape Pilate’s decision-making?
19. Why is peace gained through compromise always temporary?
20. Where do believers face similar pressures today?
21. To prepare to answer this series of questions you can review this section of the message in this link: In 1869, Charles Dickens opened A Tale of Two Cities (Timestamp 28:33 to end)
22. How are Pilate and Peter similar in their failure?
23. What makes their outcomes different?
24. Why does Pilate’s handwashing fail to bring peace?
25. What does this contrast teach about true peace?

Sermon Outline

We are reflecting during this Lenten season on events from the final week of Jesus’ earthly ministry, focusing specifically on His words. 

Luke 19:41-44 –As Jesus approached Jerusalem and saw the city, he wept over it, and said, “If only you had known on this day what would bring you peace! But now it is hidden from your eyes... because you did not recognize the time of your visitation from God.” 

Literally, it is God’s visitation. The central question in each of these weekly encounters with Jesus is this: what produces genuine, lasting peace? In today’s passage, we encounter Pilate—a man who, sadly, belongs to the very group Jesus described. He fails to recognize that he is standing face to face with the One who embodies and gives true peace. So again we ask: what makes for peace? 

In his book Perilous Pursuits (Timestamp 3:52 to 12:54), Joe Stowell tells the story of a man on a moped who pulls up to a red light. Beside him sits a driver in a Porsche, who leans out the window and dares him to a drag race. The moped rider declines at first—understandably—but after enough taunting, he finally gives in. When the light turns green, the Porsche bolts ahead, quickly leaving the moped far behind. Smiling with confidence, the driver glances in his rearview mirror—only to be stunned. The moped is somehow gaining on him, closing the distance at an unbelievable speed, until it suddenly shoots past. In moments, it becomes a distant speck. Then, astonishingly, it comes racing back in the opposite direction, blasting past him again. This strange back-and-forth continues until they both reach another red light and stop. The bewildered Porsche driver leans out and asks, “What kind of engine do you have in that thing?” The moped rider, pale and shaken, replies, “The engine’s nothing special—but would you mind unhooking my suspenders from your side mirror?” 

Pilate, though he doesn’t realize it, finds himself in a similar predicament. Despite appearances, his political “suspenders” are caught—tangled in a kind of Gordian knot with Jesus. On the surface, it doesn’t look that way, but it is, and much of it stems from his indecision. This is surprising because it doesn’t align with the Pilate we know from history. As governor of Judea, he answered directly to Caesar and held significant authority, experience, and political backing. Appointed in AD 26, he governed for about a decade, but his tenure was marked by conflict—much of it self-inflicted. Early on, he attempted to improve Jerusalem’s water supply by building an aqueduct, funding it with money taken from the temple treasury. When the people protested what they rightly saw as sacrilege, Pilate sent soldiers disguised as civilians into the crowd, who, at a signal, attacked with clubs and daggers. Luke records a similar atrocity, noting how Pilate mingled the blood of Galileans with their sacrifices (Luke 13). As James Boyce observed, Pilate was no noble figure. Ultimately, his brutality led to his recall to Rome, to answer to Emperor Tiberius. Yet before he could stand trial, Tiberius died, and Pilate faded from history—disappearing into political obscurity, a man who simply never returned. 

All of this makes his handling of Jesus all the more striking. Pilate clearly recognizes the truth. He knows what is right, what must be done, yet he cannot bring himself to act decisively. He wavers. He hesitates. On the most significant day of his life, even when he finally renders a decision, he does so reluctantly. His indecision is glaring—almost painful to watch. As an old proverb warns, “He who tries to straddle both sides of the fence will inevitably tear his trousers.” In the end, Pilate does something far worse—he tears his own soul. 

Matthew 27:1-2 – ¹Early in the morning, all the chief priests and the elders of the people made their plans how to have Jesus executed. ²So they bound him, led him away and handed him over to Pilate the governor. 

This is the final day of an already grueling week for Jesus. Matthew opens the account with a brief but weighty note: early in the morning, around 6 a.m., Jesus is handed over to Pilate for public trial, and the religious leaders ensure He is first on the governor’s docket. From start to finish, Pilate’s authority—and Jesus being handed over to him—casts a long shadow over everything that follows. In fact, this act of being “handed over” frames the entire scene. Matthew uses that phrase some fourteen times in his Gospel to describe what Jesus endures under Pilate’s authority. 

It is no surprise, then, that both the Nicene Creed and the Apostles’ Creed affirm that He “suffered under Pontius Pilate” and was crucified and buried. The religious leaders bring Jesus bound—but why? Not because He had a reputation for violence or posed any real threat. Rather, it was about appearances. Binding Him was meant to portray Him as a dangerous political criminal, to shape Pilate’s perception and make it easier to condemn Him. It was a calculated effort to dehumanize Him. The early church recognized the significance of this moment. Origen, one of our early church fathers said, “They bound Jesus, who looses those who are bound.” 

Matthew now places us in the front row of what may be the most well-known—and infamous—trial in human history. And one of its great ironies is this: the focus is not only on Jesus, the accused, but also on Pilate, the indecisive judge. It is not that Pilate lacks clarity—he knows what is right, and God ensures that he does. Nor does he believe Jesus is guilty; in fact, the opposite is true. Again and again, Pilate tries to avoid the inevitable outcome. Four times he attempts to sidestep rendering judgment, and three times he publicly declares the same verdict: Jesus is innocent of all charges.

In the end, Pilate pronounces both Jesus and himself free of wrongdoing. Yet despite this, he proves to be decisively indecisive. His hesitation becomes its own verdict—a decision that not only seals Jesus’ fate, but his own as well. 

The trial opens with Pilate’s Disingenuous Amnesty Program (Timestamp 12:55 to 16:10)—a yearly Passover prisoner release he exploits to manipulate public goodwill (Matthew 27:15-18). 

So the crowd is invited to choose a prisoner—like a first century “People’s Choice” spectacle—and Pilate’s staged performance promises drama. 

Matthew 27:17-18 – “Which one do you want... Barabbas, or Jesus who is called the Messiah?” ¹⁸For he knew... 

This passage makes clear that Pilate understood the truth: Jesus had been handed over out of self-interest. Like Joseph’s brothers before them, envy lay at the heart of their hatred and betrayal. Barabbas, by contrast, was no ordinary criminal. He was a hardened political insurgent—a man who had led rebellion against Rome and had been convicted of murder. He was well known in Jerusalem, even something of a folk hero, like a lesser, less noble Spartacus. He and at least two others were already sentenced, which may explain why three crosses stood ready that day. 

Now imagine, for a moment, that we are hearing this story for the first time. How would the crowd respond? Who would you choose if you were standing there? Pilate’s question forces an unsettling decision: what will the people do—and what would we do? Barabbas, who promises political freedom from Rome, or Jesus the Messiah, who offers spiritual freedom from sin? Which one do you want? 

Tragically, the crowd’s choice is Barabbas—the one who offers liberation from their external enemies. Jesus, who offers freedom from their deeper, internal bondage to sin, comes in a distant second. And that same question still confronts us: which one do you want? This is where the scene begins—with Pilate’s disingenuous amnesty program. 

Then Pilate's Wife Sends an Alarming Message (Timestamp 16:11 to 20:21) . Notice what she says to her husband. 

Matthew 27:19 – ¹⁹“Don’t have anything to do with that righteous man...” 

She recognizes what others refuse to see: this is a man who is clearly innocent—a conclusion even the centurion will reach later that day. Pilate’s wife sends word to her husband, sharing a deeply personal and unsettling experience—what she understands to be a supernatural warning. It comes in the form of a dream, dark and oppressive, refusing to loosen its grip on her. In that moment, God has given Pilate everything he needs to know—both the truth about Jesus and the right course of action. 

What makes her message even more remarkable is who she is. Known as Claudia Procula, she was connected to the highest levels of Roman power, the granddaughter of Caesar Augustus. Pilate’s marriage to her was a strategic move, aligning himself with influence and prestige, though hardly a model of moral virtue. Her family line was marked by scandal and excess, even by Rome’s standards. Yet here, from such an unlikely source, comes a clear and urgent witness to the truth. 

The irony is striking. At the beginning of Matthew’s Gospel, Gentile wise men recognize and honor the infant Jesus, helping preserve His life. Now, near the end, another Gentile—a woman—receives divine insight through a dream and seeks once again to spare Him. A pagan outsider proves more perceptive than the religious insiders gathered for Passover. While the devout crowd moves toward condemnation, she alone senses the gravity of what is happening. 

Meanwhile, Pilate sits on the judgment seat, the Bema Seat, unaware that he himself is being weighed. Jesus may appear to be on trial, but in reality, Pilate stands under judgment. Like the warning given to Belshazzar, the scales are already tipping—you have been weighed and found wanting. 

So the scene unfolds: first, Pilate’s disingenuous amnesty program, and now, his wife’s alarming, otherworldly warning. 

Finally, Pilate’s Capitulation to the Pragmatics of Political Life (Timestamp 20:22 to 28:22) (Matthew 27:20-26). Pilate, seasoned in the ways of political conflict, finally begins to see what is happening—but only as the pressure mounts. He seems genuinely taken aback by the raw, unrestrained fury of the crowd, directed not only at Jesus but pressing in on him as well. “Which of the two do you want me to release?” he asks. The answer comes back: Barabbas. “Then what should I do with Jesus who is called the Christ?” And they shout, “Crucify Him!” “Why? What has He done wrong?” But the response only grows louder: “Crucify Him!” 

For a people who knew well the horrors of crucifixion, the demand is staggering in its brutality. Just days earlier, they had welcomed Jesus as their Savior; now they are crying out for His execution. Their voices rise as if to command Pilate himself, something no one dared to do. It’s as though reason has given way to something darker. They have not entirely lost their senses, but they are dangerously close to the edge, blind to how far they have drifted. 

And beneath it all, though unseen, there is a deeper influence at work—a sinister presence weaving through both the crowd and Pilate himself, guiding events toward a tragic end. 

Pleased to meet you, Hope you guess my name; But what's puzzling you, Is the nature of my game. 

Sympathy for the Devil - -The Rolling Stones. 

It’s no surprise, then, that Jesus taught His disciples to pray, “Lead us not into temptation, but deliver us from evil”—or more precisely, from the evil one. And here is the crucial truth: despite all that the evil one is attempting in this moment, despite his schemes and influence, God is quietly and sovereignly at work behind the scenes. In a way that seems almost paradoxical, even evil itself is being used to accomplish the greatest good—the salvation of a lost world, people like you and me. 

In the end, Pilate chooses the path of least resistance. He yields to political pressure, bowing to the loudest voices and the shifting winds of public opinion. He hands Jesus over to brutal soldiers who eagerly mistreat Him. Then, presenting the battered and bloodied Jesus before the crowd, Pilate hopes their anger will subside—but it doesn’t. He declares again that he finds no guilt in Him, nothing deserving of death, yet his words are ignored as the situation only escalates. 

The crowd then strikes at Pilate’s greatest weakness. As John’s Gospel records, the religious leaders deliver a calculated threat: “If you let this man go, you are no friend of Caesar.” It lands like an explosive in Pilate’s mind. Already strained by prior conflicts with the Jews, he knows another misstep could cost him everything—his position, his power, his future. And he is not willing to risk it, certainly not for Jesus, and not for a people he scarcely respects. So he gives in. 

The irony is sharp. The same religious leaders who earlier feared arresting Jesus during Passover lest it spark a riot are now the very ones inciting one. They will appear to win—but their victory is hollow. And Jesus, who seems to lose in this moment, will ultimately triumph through His loss. As Romans 8:28 reminds us… 

Romans 8:28 – ²⁸And we know that for those who love God all things work together for good, for those who are called according to his purpose. 

In a final attempt to distance himself from responsibility, Pilate turns to symbolism. He takes water, washes his hands before the crowd, and declares, “I am innocent of this man’s blood.” But we’ve heard words like that before—from Judas himself. And like Judas, Pilate cannot escape the truth: despite his gestures, he is still guilty. “This is your responsibility,” he insists. “You deal with it.” It’s the same deflection the religious leaders used with Judas—a shifting of blame as old as the Garden of Eden. On this day, it seems everyone has been infected with it. 

Yet the more Pilate and the crowd try to avoid responsibility, the more they stand exposed. The people’s response is chilling: “His blood be on us and on our children.” In effect, they are saying, “We don’t care about the consequences—we just want Him gone.” Those words echo with tragic weight, foreshadowing the devastation that would come within a generation, when Jerusalem, the temple, and the nation itself were destroyed in the Roman wars of A.D. 66–70. 

So Pilate, fully aware of the truth, hands Jesus over to be crucified and releases Barabbas to the crowd. And though he may think he has washed his hands of it all, the stain remains. 

“He who did nothing wrong was condemned for everything, 

so that we who have done everything wrong would be condemned for nothing.” – Frederick Dale Bruner 

In 1869, Charles Dickens opened A Tale of Two Cities (Timestamp 28:33 to end) with those unforgettable words: “It was the best of times, it was the worst of times… an age of wisdom and an age of foolishness.” That contrast captures something of what we see here. I’m reminded of Pastor Tweedie’s sermon titled A Tale of Two Washings—a comparison between Pilate and Peter, their failures, and what each did in response. 

For Peter, despite his denial and shame, it becomes the best of times. His failure leads him back to Jesus, where he receives forgiveness, cleansing, and restoration. But for Pilate, it becomes the worst of times. In his attempt to wash his hands and absolve himself, he only deepens his guilt. One seeks cleansing on his own terms and is condemned; the other receives it as a gift and is restored. 

That brings us to a sobering truth: when it comes to Jesus, there are only two options. 

1.      Either we try to cleanse ourselves of our sin 

2.      Or we come to Him in humility and allow Him to cleanse us—by grace alone, through faith alone, in Christ alone. 

There is no third option. We must choose for or against Him; neutrality is not an option. 

So the question remains: which will you choose? Choose carefully because your eternal destiny hangs in the balance.