In this episode, Dave looks at one of the most famous, challenging, and radically counter-cultural sections of Jesus’ Sermon on the Mount: Matthew 5:38–48. Exploring the true intent behind the Old Testament principle of “an eye for an eye,” this message breaks down what it actually means to abandon personal vengeance.

Jesus isn’t asking us to be passive doormats; instead, He hands us a moral compass that points toward extraordinary generosity, gentleness, and kingdom-minded love. Through four real-world case studies—insults, possessions, time, and money—we discover how to overcome evil by reflecting the scandalous grace of Christ Himself.

Episode 07 | Matt 5:38-48 | Dave Miles | 14/06/2026

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What you will learn

  • The True Purpose of Legal Retribution: Discover how “an eye for an eye” was originally given to judges to limit punishment, rather than serve as a personal mandate for individual revenge.

  • How to Turn the Other Cheek: Learn why non-retaliation in the face of public insults is actually a brave, disarming countermove rather than passive weakness.

  • Kingdom Generosity Over Personal Rights: Explore what it looks like to hold loosely to your possessions, time, and money, opting to go the extra mile to win something far greater than a legal dispute.

  • The Ultimate Example: See how Jesus perfectly fulfilled His own radical teaching by allowing Himself to be stripped, slapped, and forced to carry a cross to purchase our rescue.

  • 00:00 – Introduction to the Law Setting the stage with the Sermon on the Mount and how Jesus unmasks the true intention of God’s law.

  • 02:08 – Misinterpreting “Eye for an Eye” Understanding the original context of Exodus and Deuteronomy: a restriction for courts, not a permission slip for personal grudges.

  • 04:48 – The Blueprint: No Personal Revenge Clarifying that Jesus is addressing individual relationships and personal conflict, not state justice or national defense.

  • 09:41 – Case Study 1: Insults and Slap Downs What it truly means to turn the other cheek when facing office politics, gossip, and public humiliation.

  • 17:50 – Case Study 2: Property and Possessions Willingness to endure personal loss and drop disputes for the sake of a higher kingdom purpose.

  • 21:19 – Case Study 3: Time and Energy The Roman soldier’s pack and what “going the extra mile” looks like when facing modern, unreasonable demands.

  • 23:16 – Case Study 4: Money and Possessions Developing a generous kingdom posture toward those in need rather than a tight-fisted, mercenary attitude.

  • 25:35 – The Gospel Example & Closing Stories How Christ lived out these exact words on His way to the cross, followed by modern examples of radical, history-making forgiveness.

  • A Compass, Not a Rigid Map: Jesus’ examples are illustrative of a fundamental heart posture, not absolute laws to be applied to the point of literalistic absurdity.

  • Turning the Cheek Retains Your Dignity: Refusing to respond in kind stands your ground, shifts the power dynamic, and forces the agressor to face their own malice.

  • Overcoming Evil with Extraordinarily Good: True Christian maturity means abandoning personal vengeance and replacing it with overflowing grace, love, and prayer for our persecutors.

  • Fueled by Grace: We can only love our enemies when we anchor ourselves in the reality that Jesus first loved and gave generously to us when we were His undeserving enemies.

Sermon on The Mount: ‘Loving Your Enemies’ (Matthew 5:28-48)

loving your enemies

[00:00:00] Hey, Soma. I’m amazed no one’s mentioned the World Cup. Come on, where’s your priorities, guys? Australia playing this afternoon. Yes. Who are we playing? I don’t even know. Turkey. Turkey? Oh, gosh. All right. Uh, that’s hard. Um, yeah, it’s good to be talking again about the Sermon on the Mount, Matthew five to seven.

[00:00:24] I’ve got three spare John Stott study guides if you want one for your group. They’re excellent studies to be going through. Jesus began the Sermon on the Mount with the Beatitudes, and then He said, “You are salt and light in the world.” And as we listen to Jesus, everything is just so refreshing, so amazing, so revolutionary, you’d have to say.

[00:00:49] And then the second half of Matthew, uh, chapter five, Jesus gives six examples of what the l- the Old Testament law, the law of God in the Old Testament [00:01:00] said, and how people were misinterpreting God’s law, and then Jesus gives His own interpretation. He shows us the true intention of the law. “You’ve heard that it was said, but I say to you,” and so far He’s dealt with anger, lust, divorce, and oaths.

[00:01:17] What will Jesus now say in chapter five, thirty-eight to forty-eight? This is an extraordinarily brilliant section of the Sermon on the Mount, and very, very, very, very, very famous. Jesus deals with infringements upon us, where somebody steps provocatively into our space. And in a world of rights and entitlements, what Jesus says is just so challenging.

[00:01:46] Here we go. We’re gonna focus on verses thirty-eight to forty-two. Matthew five, verse thirty-eight, Jesus says, “You have heard that it was said, ‘Eye for eye, and tooth for tooth.'” That’s a direct [00:02:00] quote from the Old Testament, Exodus twenty-one, twenty-four, Leviticus twenty-four, twenty, and Deuteronomy nineteen, twenty-one.

[00:02:08] And if you look back at all those references, eye for eye and tooth for tooth is a principle designed for the law courts, for judges to put an appropriate limit on the punishment that was due. But again, like the other issues Jesus has dealt with, this was being misinterpreted. It was being used by some as a justification, even a mandate, to take personal revenge.

[00:02:44] But Jesus, again, wants to make plain the original intention of the law, what God really intended. The law, eye for eye and tooth for tooth, was designed to be restrictive, not [00:03:00] retaliatory, and judicial, not personal. It’s important to understand this. Restrictive, not retaliatory. It was designed to prescribe a limit to retribution in order to discourage vengeance.

[00:03:21] Unfortunately, people often say the God of the Old Testament is a God full of vengeance, an eye for an eye, a tooth for a tooth. No. I- in the original context, this statement, an eye for an eye, a tooth for a tooth, is a statement that limits the amount of retribution. It’s restrictive, not retaliatory. It’s not about retaliation.

[00:03:48] So it’s restrictive, not retaliatory, and it’s judicial, not personal. It’s how judges are to operate. It’s the basis of [00:04:00] even our justice system today. An eye for an eye, a tooth for a tooth is the basis of our legal system. Uh, the punishment should fit the crime. The punishment should be proportional to the crime.

[00:04:15] And the point is not to use this verse as a justification to, to take justice on ourselves personally and act outside of the law, taking retribution as and when we see fit. It’s not for personal use. It’s for the nation’s legal system. So Jesus says, “You’ve heard that it, it was said, eye for eye and tooth for tooth, but I tell you, do not resist an evil person.”

[00:04:49] Now, that first line of Jesus’ response, verse nine, thirty-nine, is a summary statement, “I tell you, do not resist an evil person,” and [00:05:00] then He gives four case studies of what this looks like. And verse thirty-nine has been used over the years to validate pacifism, non-violence in any context, and the most extreme leniency towards criminals, “I tell you, do not resist an evil person.”

[00:05:25] And there have been great Christian men and women down through the century, centuries who’ve refused to go to war on the va- basis of this verse. But I don’t think that is what Jesus is getting at here. Rather, He’s responding to people misusing eye for eye, tooth for tooth, which is designed for the nation’s law courts, but individuals are using this verse to justify taking the law into their own hands and maximizing revenge.

[00:05:58] They are taking God’s [00:06:00] law out of context. So, “Do not resist an evil person” is not Jesus’ instruction for a nation’s foreign policy or defense strategy or even a nation’s legal and judicial system, and He’s not advising a citizen to reject the state’s call to go to war. That’s not the point. After all, the Apostle Paul in Romans thirteen, one to seven says, “Governments exist in order to maintain order and to punish wrongdoers.”

[00:06:36] In other words, governments exist to resist the evildoers. And Peter in one Peter two, thirteen to fourteen instructs Christians to submit to human authorities, including the emperor and the govern- uh, governors appointed by him, and he says that these teachers are sent by God to punish [00:07:00] evildoers and commend those who do what is right.

[00:07:04] So verse thirty-nine is not a blueprint for pacifism or for not defending a country against an invading army or for not prosecuting or punishing criminals. Rather, Jesus once again is referring to the Pharisaic use of this law to justify personal revenge and then say, “Well, I’ve done nothing wrong, I’ve just obeyed the law.”

[00:07:33] Jesus says, “No, you haven’t.” You’re using that law for personal vengeance. It’s meant for the legal system And the point Jesus is making is that those who belong to Jesus are to avoid personal conflict as far as possible Okay, one more comment before we look at the four case studies. These [00:08:00] four examples Jesus gives in verses thirty-nine to forty-two are illustrations of individuals relating to individuals, and these examples put flesh on the bones of what Jesus is saying.

[00:08:14] They show what it looks like when we don’t stand on our high horse and demand our personal rights. And in an age of entitlement and rights, what he says is radically counter-cultural. But what Jesus says is illustrative, um, they are not to be taken as a law and pursued to the nth degree

[00:08:43] New Testament scholar R. V. G. Tasker, Tasker says, “The following illustrations in verses 39 to 42 are not to be taken literally. They serve to drive home the point, almost to the point of absurdity, that a [00:09:00] Christian, rather than avenging himself upon a brother who has done him a personal wrong, had better go to the opposite extreme and do good to that brother.”

[00:09:14] Dick France, in his commentary on Matthew’s Gospel, makes a similar point “They are illustrations of a fundamental posture rather than literal rules to be applied literalistically” Okay, with all that in mind, let’s now look at the four illustrations, all of which are super famous. Firstly, insults and slap downs.

[00:09:44] Verse thirty-nine: But I tell you, do not resist an evil person. If anyone slaps you on the right cheek, turn to them the other cheek also. Jesus says, “If anyone slaps you on the right cheek,” assuming the person is right-handed, [00:10:00] that’s a backhanded slap And in the first century, a backhanded slap across the cheek, uh, was an expression of the greatest possible contempt The situation here is an insult rather than an assault.

[00:10:23] It is an assault in a sense, but the point is it’s an insult. It’s shaming you, it’s humiliating you to have this backhanded hit across the cheek

[00:10:40] The same word for slap is used in Matthew chapter twenty six. They spat on Jesus, struck him and somebody slapped him saying, “Prophesy to us, Messiah who struck you?” And in our world, we have tweets and whispers, gossip and [00:11:00] slander. We have all sorts of ways that people insult us, embarrass us, shame us, hurt us, malign our name.

[00:11:11] In our workplace, a comment here, a comment there. And Jesus says, um, what he says can’t be more relevant to us, “If anyone slaps you on your right cheek, turn to them the other cheek also.” In the area of insult and slap downs, don’t retaliate. In the world of office politics and gossip and banter that goes too far, don’t simmer and hold a grudge and wait for an opportunity to get even.

[00:11:49] Uh, I’ll sit there brooding, and when the opportunity comes, I’ll slip in a line that completely cuts the legs out from under that other person. Do you do that? [00:12:00] But Jesus says, “No, don’t concoct biting responses for use next time around. Nothing like that. Do not retaliate. Turn the other cheek.” You’ve heard that it was said, eye for eye and tooth for tooth, but I say to you, don’t respond in kind.

[00:12:21] To an evil person who slaps you on the ch- cheek, instead turn the other cheek. Paul picks this up in Romans twelve seventeen, “Do not repay anyone evil for evil, but be careful to do what is right in the sight of everyone.” For some of us, our workplace atmosphere would be radically transformed if everyone didn’t bear grudges about things said months ago or things said in emails.

[00:12:49] I often hear of families where members haven’t spoken to each other for decades, or people who are insulted because they didn’t get the best [00:13:00] car parking space at work. And Jesus says, “Somebody slaps you, turn the other cheek.” Remember, Jesus has just warned his disciples, “Blessed are you when people insult you, persecute you, falsely say all kinds of evil against you because of me.”

[00:13:20] And as Christians, we will see articles, blogs, Facebook entries, tweets, even coordinated campaigns against us. How are we to respond? Not in a frenzy of claim and counterclaim, not with the threat of, uh, litigation, not with self-justification and self-defense, but with turning the other cheek. Now, many have pointed out that turning the other cheek is not being a doormat.

[00:13:53] In fact, it’s quite the opposite. It’s a brave countermove. It’s not hitting [00:14:00] back, but it is standing our ground and not allowing others to take our dignity. Think of it this way. Imagine someone comes to you and berates you publicly. What if you stood your ground and calmly looked them in the eye and said, “Is there anything else that you want to say to me?”

[00:14:27] That’s turning the other cheek, right? Hit me with something else. It’s counterintuitive but effective. Martin Luther King Jr. followed Jesus’ teaching here, and in his non-violent protests, instead of fighting back, which escalates vitriol and violence, he simply stood his ground, daring his enemies to show even more [00:15:00] of their true colors It’s the opposite of being a doormat And it’s extremely effective.

[00:15:10] A friend comes to you with a snide comment, look them in the eye and say, “Is there more where that came from?” Turn the other cheek. That can be quite disarming and healing. Not necessarily, but it can be. It’s like Proverbs chapter 15, verse 1, “A gentle answer turns away wrath, but a harsh word stirs up anger.”

[00:15:39] In fact, the four examples Jesus gives are all like this. They are all examples of what Paul says in Romans 12:21, “It’s overcoming evil with good.” Someone comes to you with a, with verbal blow after verbal blow, and [00:16:00] their face is turning red as they stand there face to face with you, accusing you of everything under the sun, of being a fool, whatever it is.

[00:16:11] Each time they level an accusation, calmly say, “Is there any more?” Finally, they’ll exhaust themselves having spewed out all of their best efforts to demean you And hopefully that will bring some kind of healing By the way, this isn’t easy to do, is, is it? We need to anchor ourselves in our identity in Christ and pray and muster up our courage.

[00:16:47] This is meekness. Remember Jesus said, “Blessed are the meek, for they will inherit the earth.” Now, one really important caveat. What about an abused [00:17:00] wife, husband, or child? Are they duty-bound to simply turn the other cheek? No, this is about insult here, and it’s in the context of the law. And there is a law on domestic abuse, and the state, I’m glad to say, has ruled on such things, and therefore, the abused wife, husband, or child is quite right to act under the law and contact police or the appropriate authorities and for intervention to happen and for the legal system to do its r- uh, work So that’s quite appropriate.

[00:17:47] Well, secondly, property and possessions. Verse 40: And if anyone wants to sue you and take your shirt, hand over your coat as well. [00:18:00] Now, in Jesus’ day, many people had only three garments: a loincloth, a shirt, which was more like a dress, right? It’s full length and with a girdle or belt. Uh, not a girdle, a belt or a sash.

[00:18:16] Um, and a coat, a long coat, which protected you from the elements and doubled as your blanket at night. And many people, that’s all they own, just those three garments Clothes were very expensive. Now, to lose your shirt would be bad enough, but to lose your coat as well, for many that would be unthinkable.

[00:18:39] You’d be left without clothes and bare. But Jesus says, “If anyone wants to sue you, take, uh, and take the shirt off your back, hand over your coat as well.” Again, these are examples th- that are illustrative, not legislative. If we [00:19:00] apply this legalistically and gave everyone who wants our shirt our coat as well, we’d be left in a world of dispossessed, destitute, and naked Christians, and a w- and a world of finely c- finely clad criminals.

[00:19:16] Uh, but that’s not the point. The point is that as Christians, we ought to be quick to write off a debt, eager to pass over a wrong, willing to settle at personal loss even if we know we’re in the right. Over the years, I’ve seen Christians act on this verse at considerable personal cost. Disputes with builders dropped, disagreements over con- contracts put aside I don’t think it’s suggesting that we will never end up in court with a neighbor But it does [00:20:00] dramatically temper the attitude we approach a dispute with might there be something bigger and better to be gained?

[00:20:10] If we don’t stand up for our rights

[00:20:15] And we will get into disputes with people, wrongful dismiss-missiles, people seeking retribution in the law courts. What a radical difference it would make if we Christians lived as Jesus suggests and simply let it drop, or if, if we were to give what they ask for and even more Give our coat as well. If we overflow in generosity, though the, though, even though the demand is unreasonable, could there be something bigger and better gained than our rights?

[00:20:54] Well, that’s something to work out case by case. And again, these are illustrative [00:21:00] of a general posture, not laws that are to be taken too legalistically. You’ve heard that it was said, “Eye for eye and tooth for tooth,” but anyone, if they want to sue you, take your sh- shirt off your back, hand over your coat as well.

[00:21:17] Thirdly, time and energy. Verse 41: If anyone forces you to go one mile, go with them two miles. In Jesus’ day, the Roman soldiers had the right to commandeer any individual to carry his pack for a mile at the drop of a hat, at any time, and they used this law to really humiliate the Jews. You’re on your way to work, you’re on your way to the synagogue, you’re on, on your way to school, whatever, a soldier walks around the corner, “Hey, you, here’s my pack.

[00:21:49] Carry.” And you had to carry his pack for an entire mile, even though it was heavy. Male, female, [00:22:00] child, doesn’t matter Now, is there a twenty-first century parallel? I suggest that in the modern work world there are any number of examples of this, maybe less absolute than a Roman soldier with a sword. But there are many examples of individuals being asked to perform unreasonable tasks with inappropriate levels of threat, the threat of losing your job or whatever.

[00:22:31] It’s kind of the way of the world, isn’t it? To be forced into doing something inconvenient and unreasonable by your superiors. What an opportunity for Christians to be radically different. If anybody forces you to go one mile, go with them two miles. Go to your boss and say, “Is there anything else I can do?”

[00:22:57] Once again, it’s not to be [00:23:00] applied legalistically, otherwise we’d all be worked to the bone and we wouldn’t ever get home from work. Rather be known as the person who often goes the extra mile Fourthly, money. Verse 42: “Give to the one who asks you, and do not turn away from the one who wants to borrow from you.”

[00:23:26] Again, a literal application of this could be self-defeating. One author said there will be a class of saintly paupers owning nothing, and another class of prosperous thieves. But Jesus is saying, “Don’t have a mercenary, tight-fisted, penny-pinching attitude to money in the face of need. Don’t say to a beggar, ‘Too bad, you should have tried harder in your life.'”

[00:23:56] Now, in Jesus’ day, in the context of a less [00:24:00] mobile, largely static rural population, it would have been easier to spot the person who was in genuine need over and against somebody taking an advantage. In our world, it’s sometimes better to offer food rather than money, as many of you know. I’ll buy you a cup of coffee or I’ll buy you lunch.

[00:24:19] I’ll get you an Opal card if you ne- need transport. That might be the wise thing to do, or contact the relevant health authorities or the ambulance, uh, if the person is in urgent need of medical help. I… Glenda says, who works with people in these situations down in Sydney, says that concerned bypassers do this a lot.

[00:24:45] They’ll ring up, for example, the homeless health team in the city, which goes around looking after the health of homeless people, uh, for example. They’ll ring up about a particular person who is in desperate straits. [00:25:00] Uh, and people are great at doing that, which is fantastic. Jesus is giving us a com- compass here, not a map.

[00:25:10] I think that’s a good way to say it. He’s pointing us in a direction. He’s not giving us directions Uh, he’s saying, “What’s your basic attitude? Penny-pinching, money-grabbing, it’s my money, you’re not getting any of my money, or is it the generous attitude of Christ?” So overall, Jesus is addressing people who are trying to justify exacting personal revenge on anybody who has insulted them, sued them, exploited, or taken advantage of them, and using God’s law to justify that.

[00:25:53] And Jesus calls us to abandon personal vengeance, surrender our [00:26:00] rights, and instead overcome evil with extraordinary generosity, gentleness, and love. And he goes on to say in verses 43 to 48, “Love your enemies and pray for those who persecute you”, which kind of summarizes the whole thing. There was once a man, he was on trial, and he was asked a very difficult question, “Tell us, are you the Christ, the Son of God?”

[00:26:30] And the man on trial gave a plain, straightforward answer, because that was exactly who he is. What happened next? Well, if that’s who he is, he has every power imaginable, and yet he allowed himself to be struck, to be slapped in the face, to be stripped of all of his garments. Others even [00:27:00] cast lots for them, and then the Roman soldiers compelled him to carry his cross as far as he could.

[00:27:10] But that’s not all that Jesus was willing to carry. He did go the extra mile, although in truth, that doesn’t even begin to describe what Jesus did. He did not only carry a wooden cross, but also took upon himself the sins of the world. He wasn’t obligated to. He had never sinned, but he chose to take on the sins of others, to take them to the cross, to suffer the agonizing consequences, paying the price of a ransom for many.

[00:27:46] And as a result, when you or I come begging… With no right to claim anything from him, asking for rescue [00:28:00] He gives generously Aren’t we thrilled that Jesus listened to his own teaching? He spoke the truth, which we saw last week. He turned the other cheek. He went the extra mile. He gives graciously, abundantly to the undeserving.

[00:28:23] He loved his enemies and prayed, “Father, forgive them.” He showed us by example what life in his kingdom looks like. So let’s turn the other cheek, give them our coat as well, go the extra mile, and give to the one who asks us. Two quick stories to close. There was a young Christian boy in primary school, and this bully named Derek was just constantly making this Christian boy’s life a living hell.

[00:28:56] And his mom, who’s also a Christian, said, “Okay, here’s the [00:29:00] plan. We’re going to have Derek over to play tomorrow afternoon.” And this Christian boy said, “What? What? No way.” Um, but they talked about it and he agreed. And of course, his mom thought carefully about whether that was appropriate. But he asked Derek to come over and play the next day and Derek came over, had a great time, and true story, from that day on, Derek, the former bully, was the kindest, most faithful friend to this guy.

[00:29:34] Uh, he was like this Christian boy’s protector at school . And that’s what Jesus is talking about, not retaliating, but overcoming evil with good. Second story, in January 1999, Australian missionary Graham Staines and his sons, six years old and 10 years old, were mobbed [00:30:00] by radical Hindus. They were trapped inside their car in Orissa, India and burned alive.

[00:30:08] Afterwards, their three charred bodies were still clinging to each other. He’d spent 34 years working with lepers in Orissa. He left his widow and daughter behind. Her response got into every paper in India. She said, just a few days after her husband and sons were killed, “I have only one message for the people of India.

[00:30:35] I’m not bitter, neither am I angry, but I have one great desire, that each citizen of this country should establish a personal relationship with Jesus Christ who gave his life for our sins. Let us burn hatred and spread the flame of Christ’s love.” Everyone thought she would come back to [00:31:00] Australia. She didn’t.

[00:31:02] She said God had called her to India and she wouldn’t leave. She said, “My husband and our children have sacrificed their lives. For this reason, India is my home. I hope to be here and continue to serve the needy.” Amen.

  1. The Grudge Check: Is there an insult, a snide email, or an office slight that you are secretly simmering over? How does Jesus’ command to “turn the other cheek” alter your strategy for handling that person next time you see them?

  2. Rights vs. Rescue: When you get into personal or financial disputes, is your default reaction a frantic defense of your individual rights, or do you ask yourself if there is “something bigger and better to be gained” by letting it drop?

  3. The Extra Mile at Work: What is a practical, modern equivalent of being forced to carry a heavy pack for a mile in your workplace? How can you transform an inconvenient demand from a superior into an opportunity to showcase kingdom generosity?