The Great Exchange, Part 1

The Gospel of Matthew  •  Sermon  •  Submitted   •  Presented   •  57:56
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September 28, 2025

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Text: Matthew 27:1-10
Introduction: I had originally planned to do this entire chapter in one message so that we could wrap up our series in Matthew in time to start another series I have planned, but as I dug into this passage, I realized I had three options. 1) I could hold you here for three hours to unpack this chapter (and then leave the last chapter of Matthew for whoever you select to replace me as your next pastor!), 2) fly through this passage so quickly that we don’t have time to really do it justice, or 3) break it up into separate messages and extend the Matthew series a little bit. Since I’m not in a hurry to put out resumes and I can’t stomach the idea of rushing through arguably the most important event in redemptive history, we’re going to extend the Matthew series a couple extra Sundays. So, this is part 1 of what is (currently planned to be) a three-part mini-series within our Matthew series that I’m calling the Great Exchange.
As we look through this passage, I want to draw your attention to the exchanges that take place. In some ways, I think we could probably somewhat accurately summarize our lives and what is important to us by describe the exchanges that we make.
Sometimes, we’re not even consciously aware of the exchanges we make. When a young married couple decides to have a baby, rarely do they consider that they are making an exchange. They’re exchanging the peaceful, quiet evenings alone for rowdy, noisy, stressful evenings and late night feeding sessions. They’re exchanging a life of focus on self-fulfillment and their own needs for a life focused on the needs of another little human being.
Main Point/FCF: What kind of items we purchase, how we spend our time, what we is worthy of our hard work, all of these are an exchange that tells something about what we value and what we believe. But, if we’re not careful, we can allow the kingdom of this world to so influence us that we subconsciously make exchanges that devalue the things of God and demonstrate a love for things that are not of God.
So, in this first part of Matthew 27, I want us to look at Judas’ exchange.
Matthew 27:1–10 ESV
1 When morning came, all the chief priests and the elders of the people took counsel against Jesus to put him to death. 2 And they bound him and led him away and delivered him over to Pilate the governor. 3 Then when Judas, his betrayer, saw that Jesus was condemned, he changed his mind and brought back the thirty pieces of silver to the chief priests and the elders, 4 saying, “I have sinned by betraying innocent blood.” They said, “What is that to us? See to it yourself.” 5 And throwing down the pieces of silver into the temple, he departed, and he went and hanged himself. 6 But the chief priests, taking the pieces of silver, said, “It is not lawful to put them into the treasury, since it is blood money.” 7 So they took counsel and bought with them the potter’s field as a burial place for strangers. 8 Therefore that field has been called the Field of Blood to this day. 9 Then was fulfilled what had been spoken by the prophet Jeremiah, saying, “And they took the thirty pieces of silver, the price of him on whom a price had been set by some of the sons of Israel, 10 and they gave them for the potter’s field, as the Lord directed me.”

Judas exchanged the Messiah for money.

As we’ve already seen, Judas Iscariot—one of Jesus’ 12 disciples in his inner circle—betrayed Jesus for the sum of 30 pieces of silver (amounting to a few thousand dollars). Having received the bribe from the priests, Judas began to look for an opportunity to hand Jesus over to the authorities when there weren’t crowds present that might prevent his arrest.
Matthew 26:14–16 ESV
14 Then one of the twelve, whose name was Judas Iscariot, went to the chief priests 15 and said, “What will you give me if I deliver him over to you?” And they paid him thirty pieces of silver. 16 And from that moment he sought an opportunity to betray him.
Judas, of course, gets his opportunity at the end of ch. 26 as Jesus is in the Garden of Gethsemane with only his core group of disciples. Judas betrays Jesus with a kiss on the cheek as his pre-arranged sign, and Jesus is arrested.
There’s a lot about Judas’ actions in this story that we don’t know. We see that Judas “changed his mind” in this passage, which makes us wonder if perhaps he didn’t really think Jesus would be put to death, and now that he realizes where this is heading, he’s filled with remorse.
Some have speculated that perhaps Judas wanted to “force Jesus’ hand,” to get him to declare himself the Messiah and use his supernatural powers to overthrow the Romans and the corrupt temple officials. Then, when Judas realizes that Jesus isn’t going to do that, he panics and tries to undo it.
We don’t really know a whole lot about his motives or his inner thoughts, but Scripture makes one thing very clear:

Judas’ actions reveal a love of money.

As we saw a couple of weeks ago, when Jesus is anointed in Bethany by Mary the sister of Lazarus, this is a tipping point for Judas.
Mary, the sister of Lazarus—a man that Jesus had raised from the dead just a few weeks prior—comes to Jesus and anoints him with an expensive perfume. The disciples estimated the value of the perfume at roughly one year’s wages for a day-laborer—tens of thousands of dollars! And she pours it out over Jesus.
John’s gospel gives us a little more insight to Judas than Matthew does:
John 12:3–6 ESV
3 Mary therefore took a pound of expensive ointment made from pure nard, and anointed the feet of Jesus and wiped his feet with her hair. The house was filled with the fragrance of the perfume. 4 But Judas Iscariot, one of his disciples (he who was about to betray him), said, 5 “Why was this ointment not sold for three hundred denarii and given to the poor?” 6 He said this, not because he cared about the poor, but because he was a thief, and having charge of the moneybag he used to help himself to what was put into it.
We find out here that Judas had been embezzling money from the disciples’ ministry account for some time.
Probably the disciples didn’t put it all together until after the fact, but it’s clear that Judas had a problem with money.
We can speculate on what Judas’ motives were all day long, but at the end of the day, Judas made an exchange: his Messiah, his King, his Lord, his friend, for what amounts to a few thousand dollars.

Love of money brings destruction.

In our society, love of money is tolerated and even praised. Those who are rich and prosperous are loved and adored and bookshelves and social media is filled with schemes to help you get rich quick. Sometimes we like to rephrase and rebrand it though to make it sound a little less greedy and we call it “Building wealth.”
At the end of the day, though, Jesus said:
Matthew 6:19–24 ESV
19 “Do not lay up for yourselves treasures on earth, where moth and rust destroy and where thieves break in and steal, 20 but lay up for yourselves treasures in heaven, where neither moth nor rust destroys and where thieves do not break in and steal. 21 For where your treasure is, there your heart will be also. 22 “The eye is the lamp of the body. So, if your eye is healthy, your whole body will be full of light, 23 but if your eye is bad, your whole body will be full of darkness. If then the light in you is darkness, how great is the darkness! 24 “No one can serve two masters, for either he will hate the one and love the other, or he will be devoted to the one and despise the other. You cannot serve God and money.
Judas tried to serve two masters. But in the end, money was his true love.
See, money brings security, confidence in the future. Those whose bank accounts and retirement accounts are well-funded don’t have to worry about the future. But the problem is that Scripture tells us to find our peace and assurance and confidence not in our bank account, but in the love and providence of our Heavenly Father.
Matthew 6:31–32 ESV
31 Therefore do not be anxious, saying, ‘What shall we eat?’ or ‘What shall we drink?’ or ‘What shall we wear?’ 32 For the Gentiles seek after all these things, and your heavenly Father knows that you need them all.
Money promises “Find me and you find happiness!” but Jesus says,
Matthew 6:33 ESV
33 But seek first the kingdom of God and his righteousness, and all these things will be added to you.
Money promises power and prestige, admiration of your peers. But Scripture says
Matthew 23:11–12 ESV
11 The greatest among you shall be your servant. 12 Whoever exalts himself will be humbled, and whoever humbles himself will be exalted.
Money provides comfort and ease, but Jesus said:
Matthew 16:24 ESV
24 Then Jesus told his disciples, “If anyone would come after me, let him deny himself and take up his cross and follow me.
1 Timothy 6:6–10 ESV
6 But godliness with contentment is great gain, 7 for we brought nothing into the world, and we cannot take anything out of the world. 8 But if we have food and clothing, with these we will be content. 9 But those who desire to be rich fall into temptation, into a snare, into many senseless and harmful desires that plunge people into ruin and destruction. 10 For the love of money is a root of all kinds of evils. It is through this craving that some have wandered away from the faith and pierced themselves with many pangs.
So, heed the warning of Judas’ life and do not make the trade that he made.
Hebrews 13:5 ESV
5 Keep your life free from love of money, and be content with what you have, for he has said, “I will never leave you nor forsake you.”

The key to a life free of the love of money is a life filled with love for Jesus.

If I tell you, “Don’t think about pink elephants,” I can bet that every single person in this room is now thinking about pink elephants.
The key to ridding your life of the love of money is to fill your life with love for Jesus.
The sad irony of Judas’ exchange is that he traded the greatest treasure in the universe for a few dollars. If he had only realized who was standing right in front of him! The source of life, the one who satisfies our deepest desires and longings, the one through whom Creation came to exist!
What comfort can money provide that Jesus cannot provide in greater abundance? What honor and prestige can money purchase that being an heir of the King of Heaven cannot give? What happiness, joy, and satisfaction can money provide that an eternity with God cannot make pale in comparison?

Judas exchanged heaven for hell.

Matthew 27:6–8 ESV
6 But the chief priests, taking the pieces of silver, said, “It is not lawful to put them into the treasury, since it is blood money.” 7 So they took counsel and bought with them the potter’s field as a burial place for strangers. 8 Therefore that field has been called the Field of Blood to this day.
Judas bribe money couldn’t be put into the Temple treasury because OT Law forbade the use of funds gained through illegal or immoral means to be given as a tithe (which is an ironic admission by the priests of their own wrongdoing). So, instead, the priests used it to purchase the field where Judas hung himself as a burial ground for non-Jews. As Matthew 27:8 tells us, it became known as the “Field of Blood.”
While we cannot have 100% scientific certainty of the location of Akeldama, sources dating back to the fourth century place it in the Valley of Hinnom, also known as the Valley of the Sons of Hinnom. There’s enough agreement on this that there seems to be no reason to doubt it.
What is interesting about this location is that the Valley of Hinnom was the same valley in which several of the most wicked kings of Israel, including Ahaz and Manasseh, performed child sacrifices to the pagan god Molech.
2 Chronicles 33:6 ESV
6 And he burned his sons as an offering in the Valley of the Son of Hinnom, and used fortune-telling and omens and sorcery, and dealt with mediums and with necromancers. He did much evil in the sight of the Lord, provoking him to anger.
This valley became so associated with evil and defilement (for obvious reasons) that most Jews refused to build homes there or use it for normal purposes.
So, it became the location where the residents of Jerusalem would burn their trash. It was basically a dump that always stunk of refuse and rottenness and was constantly filled with fire and smoke.
Over time, it came to be used as a metaphor to describe the eternal torment of separation from God that awaits unbelievers. It was called, “Gehinnom” or “Gehenna.” So, when Jesus spoke of Hell, this is the Greek word he normally used—Gehenna.
Matthew 5:29–30 ESV
29 If your right eye causes you to sin, tear it out and throw it away. For it is better that you lose one of your members than that your whole body be thrown into hell (gehenna). 30 And if your right hand causes you to sin, cut it off and throw it away. For it is better that you lose one of your members than that your whole body go into hell (gehenna).
So, why am I telling you all this? The field that was purchased with Judas’ blood money was, according to early church fathers and historical writings, in the Valley of Hinnom. The money that Judas received for betraying Christ—both literally and figuratively—bought him a place in Hell.
Judas’ focus on the material things of this life ultimately cost him the immaterial things of the life to come.
I remember as a young minister hearing a warning from some who thought that pastors were out of touch with reality. They would say, “He’s so heavenly minded he’s no earthly good.”
I’ll confess that if that charge is ever leveled against me, I’ll wear it proudly as a badge of honor. Because from where I’m standing, the greatest problem plaguing the church today is not that its people are too heavenly minded but that they are too worldly. Carnal people obsessed with money and power and comfort and ease in this life—what will that gain you in eternity?
What good is it if you know how to interpret the market but you can’t interpret God’s word? What good is it if you know all your favorite team’s stats but you don’t have God’s word hidden in your heart? What good is it if you are well-known and loved by everyone at school but you’re not known by God?
We need more Christians with their heads in the clouds, with their eyes focused on eternity. We need Christians who care more about the life to come than they do about this life. We need more Christians willing to exchange this world for the next.
What about you? We all are making an exchange, a trade. One life for the other. Which one are you trading?

Judas exchanged repentance for regret.

Now, you might be tempted to think that Judas here is repentant of his sins. After all, he tries to return the money and he acknowledges that he has sinned. The KJV even uses the word “repented”:
Matthew 27:3 KJV 1900
3 Then Judas, which had betrayed him, when he saw that he was condemned, repented himself, and brought again the thirty pieces of silver to the chief priests and elders,
But, the underlying Greek word is not the word that is typically used of repentance. The word for repentance is metanoia whereas the word here is metamelomai. Typically, this word means either simply “to change one’s mind” or—as is clear here—“to be filled with regret.”
The word that is used in verse three does not occur often in Scripture, but interestingly it occurs in 2 Corinthians 7 alongside metanoia so that we can compare the two.
In this passage, Paul mentions a tough letter he had previously written to the Corinthians that had caused them a lot of pain.
2 Corinthians 7:8 ESV
8 For even if I made you grieve with my letter, I do not regret (metamelomai) it—though I did regret (metamelomai) it, for I see that that letter grieved you, though only for a while.
What is interesting about this is that Paul says he felt conflicted about that letter. If we sum up Paul’s feelings, what Paul felt was that he was sorry for the pain, the consequences, of his letter, but ultimately felt that the letter was necessary. He found the pain “regrettable,” but he stood behind his decision to write it.
Paul says that he found their pain “regrettable,” Paul goes on to say this:
2 Corinthians 7:8–10 ESV
9 As it is, I rejoice, not because you were grieved, but because you were grieved into repenting (metanoia). For you felt a godly grief, so that you suffered no loss through us. 10 For godly grief produces a repentance (metanoia) that leads to salvation without regret (metamelomai), whereas worldly grief produces death.
Here, Paul contrasts the fleeting “regret” (metamelomai) for the pain his letter caused with the ultimate goal of the goodness of the “repentance” (metanoia) that this letter produced. The Corinthian church chose to repent of their sins, so they received salvation without regret. Repentance frees you from regret.
Now, that, obviously, is a positive use of the word. But here we see something else happening. Judas is filled with regret (metamelomai), but not repentance.
He doesn’t pray and confess his sin, he doesn’t prostrate himself before Jesus and ask for forgiveness. Instead of going to God for forgiveness, he attempts to get it from the priests. It’s a regret for the outcome of his actions, but not repentance for the actions themselves.
Judas made a trade. He traded repentance for regret. He chose not to repent of his sins, which would have brought the temporary agony and humiliation of admitting his wrongdoing and humbling himself before the one he had wronged but would have brought freedom and restoration and forgiveness. Instead, he chose to wallow in regret, and his cost him his life and his eternal destiny.
That is where regret leads. Many people nowadays are filled with regret for things they have done. You don’t have to be a Christian to feel regret for bad choices. But, simply acknowledging that you’ve done wrong and wishing you had done differently is not enough.
But, repentance is when you not only acknowledge that you’ve done wrong but that Jesus has done right and will do right. There’s a beautiful expression of repentance in Psalms, written by David after he committed adultery with Bathsheba and then conspired to have her husband killed to cover up his affair.
Psalm 51:1–17 ESV
1 Have mercy on me, O God, according to your steadfast love; according to your abundant mercy blot out my transgressions. 2 Wash me thoroughly from my iniquity, and cleanse me from my sin! 3 For I know my transgressions, and my sin is ever before me.
Notice that David goes straight to God with his prayer and appeals for mercy. He acknowledges his sins, but then he reaches out in faith to God for mercy.
Psalm 51:1–17 ESV
4 Against you, you only, have I sinned and done what is evil in your sight, so that you may be justified in your words and blameless in your judgment.
David acknowledges not only that he has sinned, but that God is righteous and just to condemn him and inflict whatever punishment God sees fit.
Psalm 51:1–17 ESV
7 Purge me with hyssop, and I shall be clean; wash me, and I shall be whiter than snow. 8 Let me hear joy and gladness; let the bones that you have broken rejoice. 9 Hide your face from my sins, and blot out all my iniquities. 10 Create in me a clean heart, O God, and renew a right spirit within me. 11 Cast me not away from your presence, and take not your Holy Spirit from me. 12 Restore to me the joy of your salvation, and uphold me with a willing spirit.
David doesn’t just stop with regret for his sins, he continues in faith in God’s goodness and mercy. David has faith that God can restore him, cleanse him. He doesn’t run away from God but instead begs God not to take away his presence from David’s life.
Psalm 51:1–17 ESV
13 Then I will teach transgressors your ways, and sinners will return to you. 14 Deliver me from bloodguiltiness, O God, O God of my salvation, and my tongue will sing aloud of your righteousness.
David’s repentance is filled with hope that God can and will restore him, even to the point that David would one day be able to teach other sinners about God’s mercy. David’s repentance is filled with praise to God.
Psalm 51:1–17 ESV
15 O Lord, open my lips, and my mouth will declare your praise. 16 For you will not delight in sacrifice, or I would give it; you will not be pleased with a burnt offering. 17 The sacrifices of God are a broken spirit; a broken and contrite heart, O God, you will not despise.
David’s repentance comes from the heart and acknowledges that what God wants most from him is not outward conformity to his Law but an inward heart that loves God. His prayer of repentance is filled with hope and confidence in the goodness and mercy of God.
See, regret is like repentance without faith. Regret says “I’m a sinner and I’m doomed!” Regret is like Ephesians 2:1-3 without the rest of the passage:
Ephesians 2:1–3 ESV
1 And you were dead in the trespasses and sins 2 in which you once walked, following the course of this world, following the prince of the power of the air, the spirit that is now at work in the sons of disobedience— 3 among whom we all once lived in the passions of our flesh, carrying out the desires of the body and the mind, and were by nature children of wrath, like the rest of mankind.
And the difference is that regret stops right there. It wallows in self-loathing and self-pity because regret is all about self.
But repentance says,
Ephesians 2:4–7 ESV
4 But God, being rich in mercy, because of the great love with which he loved us, 5 even when we were dead in our trespasses, made us alive together with Christ—by grace you have been saved— 6 and raised us up with him and seated us with him in the heavenly places in Christ Jesus, 7 so that in the coming ages he might show the immeasurable riches of his grace in kindness toward us in Christ Jesus.
Because repentance is all about God.
Regret is a tool of Satan, and its end is destruction. Repentance is a work of the Holy Spirit, and its end is eternal life and freedom.
Reflection Questions:
How do the exchanges we make in our lives reflect our true values and beliefs?
In what ways might we be tempted to value money or possessions over our relationship with God?
What are some practical ways we can prioritize our spiritual life over material wealth?
What is the difference between true repentance and mere regret?
What exchanges do you see people making at school, work, and daily life?
What exchanges are you making to keep your focus on eternity? What exchanges do you find difficult, and why?
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