Introduction:

In January we began preaching through the Sermon on the Mount. We began by focusing on Jesus' first message. The call to repent. To turn from the old ways of living and to follow in His footsteps. We noted that repentance is the doorway we must all pass through to enter into the Kingdom of God. After that we looked to the beatitudes, the blessed teachings of Jesus. Each beatitude built upon the previous one, like a heavenly staircase leading us upward to ever higher levels of Christ-likeness. While the beatitudes are not easy, they are the signs we should expect to see in a life focused on Christ. Then we spent the last two weeks focusing on Jesus’ teachings about the Old Testament Law and its right application. We looked at things like adultery, divorce, and taking oaths to see that God wants more than just rule keeping. He wants a heart that makes the rules unnecessary and the sins they prevent unthinkable. Finally, last week we looked at Jesus’ teachings on murder and hatred. We saw how the sin we might be quickest to point to and say “Well at least I never did that” may actually be the most prevalent sin in our lives. We saw how murder is just the most extreme manifestation of the sin of hatred and contempt, and how even though the sin might never manifest as violence in us, that does not mean the seed is not there or that the roots have not taken hold. 

This week we will be continuing our journey through the Sermon on the Mount by looking at Matthew 5:38-44. Here Jesus focuses on the law of retaliation. Like last week, this may be a difficult teaching to accept. Even though Jesus teaches us that obedience to him will cost us greatly, we all would like to think that the cost is not that great, or that somehow it is a cross for others to bear but not for me. There is a dangerous temptation when reading and preaching teachings like this to try to water them down until we are all but ignoring the clear teachings of Jesus. This is what the Pharisees did to the Law of God, and Jesus was preaching this very message to them, so it would be an ultimate disservice to Jesus and to you if I softened the words of Jesus to make them more palatable. I want to teach these passages in the context in which they were preached, and I want to teach with the full range of scripture in mind, but I never want to avoid teaching just because it is hard to swallow. 

With this in mind, let us read from God’s Word:  

Scripture Reading:

“You have heard that it was said, ‘Eye for eye, and tooth for tooth.’ 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. And if anyone wants to sue you and take your shirt, hand over your coat as well. If anyone forces you to go one mile, go with them two miles. Give to the one who asks you, and do not turn away from the one who wants to borrow from you. “You have heard that it was said, ‘Love your neighbor and hate your enemy.’ But I tell you, love your enemies and pray for those who persecute you…”  Matthew 5:38-44 (ESV) 

I. The Law of Retaliation (Matthew 5:38)

Jesus begins this teaching on retaliation by quoting an established Old Testament principle: 

"You have heard that it was said, ‘Eye for eye, and tooth for tooth.’" (Matthew 5:38, ESV). This paraphrase was a reference to a few passages in the Old Testament Law. 

"But if there is harm, then you shall pay life for life, eye for eye, tooth for tooth, hand for hand, foot for foot, burn for burn, wound for wound, stripe for stripe." (Exodus 21:23-25, ESV)

"Fracture for fracture, eye for eye, tooth for tooth; whatever injury he has given a person shall be given to him." (Leviticus 24:20, ESV)

"Your eye shall not pity. It shall be life for life, eye for eye, tooth for tooth, hand for hand, foot for foot." (Deuteronomy 19:21, ESV). 

In legal terms, this is referred to as the principle of “Lex Talionis” or “the law of retaliation” and it is a foundational principle in legal thought, even today. The idea is fairly simple, but it provides a necessary framework for legal justice. “Lex Talionis” means that the punishment should be proportional to the crime. 

It is not difficult to see why this principle is necessary in any just society. Imagine we are in the ancient world and you stole a donkey  from me. In retaliation I decided to burn down your crops. You then retaliated by kidnapping my daughter, and I retaliated by gathering my family to go and kill your family. You can see how this easily escalates. 

In a world where revenge can easily spiral out of control, leading to blood feuds and escalating violence, the law of retaliation served as a moderating force, ensuring that punishment was proportional to the crime. It was, at its core, a principle of equity rather than excess. When someone wrongs you, you could pursue justice, but the justice had to be legal and proportional. 

Unfortunately, like many good things in the Old Testament Law, what began as a protective law would, in time, become a loophole to excuse sinful actions. Though originally designed to be implemented by courts and governing authorities, the law of retribution was increasingly being cited by individuals seeking revenge on one another. Rather than relying on the judicial system to execute fair and balanced justice, many took the law into their own hands, used “eye for an eye and tooth for a tooth” as an excuse for personal retaliation. 

With this context in mind, Jesus speaks to something new and radically different. Man desires to punish those who wrong them. The law desires to make sure the punishment matches the crime. Jesus desires a higher way for his followers, not simply the way of justice, but of mercy and grace. He is teaching the principle that Paul would later write about in his letter to the church in Rome, where he declares, “Do not be overcome by evil, but overcome evil with good.” (Romans 12:21, ESV). 

Now I do not believe that this is a call to ignore wrongdoing. That would be unjust. I do, however, believe that Jesus is calling all of his followers, including you and me, to respond to injustice in a way so radical that it disrupts the cycle of vengeance. The Christian is not to be a passive bystander but an active participant in God’s redemptive work. Through grace, we are called to forgiveness, because in forgiving, we reflect the heart of our Father in heaven.  

II. Jesus’ Radical Reversal (Matthew 5:39-42)

In Matthew 5:39, Jesus delivers a command that must have startled His audience: "But I say to you, Do not resist the one who is evil." (Matthew 5:39, ESV). At first glance, this command seems to advocate passivity in the face of evil or injustice. Jesus is not advocating for the abdication of justice, nor is He promoting lawlessness or absolute pacifism. Rather, He calls His followers to renounce personal vengeance and to refuse participation in the endless cycle of retaliation. Instead, Jesus commands His disciples to trust in God’s justice and to embody the  countercultural ethic of the kingdom, one that does not respond to evil with evil but overcomes it with good (Romans 12:21).

To illustrate this principle, Jesus provides four real world examples, each one dismantling the human tendency toward revenge and advocating for a response that reflects the heart of God’s kingdom.

Turn the Other Cheek 

Jesus begins with an illustration that would have been instantly understood by His first-century listeners: "But if anyone slaps you on the right cheek, turn to him the other also." (Matthew 5:39, ESV). In ancient Jewish culture, to be struck on the right cheek typically meant receiving a backhanded slap from a right-handed aggressor. This was not an act not of violence, as in a fight. This is not a teaching against self-defense. No, in this culture a “slap to the right cheek” is a deep insult. According to rabbinic law, a backhanded slap was considered twice as offensive as a slap with an open palm.

By commanding His disciples to turn the other cheek, Jesus was not instructing them to be passive doormats. Rather, He was advocating a response that exposes the futility of retaliation. Turning the other cheek is an assertion of moral strength, demonstrating that my dignity is not dictated by the insult of another but is anchored in God. This echoes Proverbs 19:11: "Good sense makes one slow to anger, and it is his glory to overlook an offense."

Give Your Cloak

Jesus continues with a second example: "And if anyone would sue you and take your tunic, let him have your cloak as well." (Matthew 5:40, ESV). Under Jewish law, a creditor could sue for a debtor’s tunic (the inner garment), but the cloak (outer garment) was considered essential for survival and could not be permanently taken (Exodus 22:26-27). Yet Jesus instructs His followers to voluntarily surrender even their cloak. This may be a hard truth for us to swallow, but the kingdom of God is not built on personal rights but on radical generosity. By going beyond what is legally required, the disciple demonstrates that his security is not in material possessions but in God’s provision. This teaching aligns with Paul’s exhortation in 1 Corinthians 6:7: "To have lawsuits at all with one another is already a defeat for you. Why not rather suffer wrong? Why not rather be defrauded?" The willingness to relinquish one’s cloak serves as a powerful testimony to a world obsessed with self-preservation and entitlement.

Go The Second Mile

Jesus' third example comes from a common experience in Roman occupied Israel: "And if anyone forces you to go one mile, go with him two miles." (Matthew 5:41, ESV). Roman law permitted soldiers to compel civilians to carry their burdens for one mile. Some think this is what happened when the Roman soldiers demanded that Simon of Cyrene carry Jesus’ cross during his crucifixion. This practice was deeply resented by the Jews, as it symbolized the humiliation of foreign occupation.

Yet Jesus calls His followers to not only comply but to go beyond what is demanded. This voluntary act of service transforms forced labor into an act of willing service to God. It shifts the power dynamic, turning an oppressive imposition into an opportunity to display the love and grace of Christ. This radical response finds a parallel in Philippians 2:3-4: "Do nothing from selfish ambition or conceit, but in humility count others more significant than yourselves. Let each of you look not only to his own interests, but also to the interests of others." By willingly going the second mile, the disciple reflects the heart of a servant, one who does not see burdens as obligations, but as opportunities to reflect the nature of Christ (Mark 10:45).

Give To The One Who Begs

Finally, Jesus states: "Give to the one who begs from you, and do not refuse the one who would borrow from you." (Matthew 5:42, ESV). This statement builds upon the previous examples, challenging His disciples to embrace a posture of open-handed generosity. In a world marked by greed and self-interest, Jesus calls His followers to be conduits of God’s generosity.

In my personal experience, this may be one of the harder teachings to follow well. I do not believe that Jesus is advocating that we give in a way that enables destructive behavior. I believe that Jesus would affirm all the principles of biblical stewardship and discernment in scripture. For instance, 2 Thessalonians 3:10 states: "If anyone is not willing to work, let him not eat." We know that the Bible does not contradict itself, so there must be a balance between generosity and wisdom, but I will freely admit that it is hard to find. 

Back in Mississippi I was the person at my church who handled benevolence requests, and we got them several times a week. The place I served in had some rampant drug use and prostitution. A lot of people came to gamble on the river boats, lost it all, and found themselves stuck. There were always homeless people hanging around the bus stops just across the street from my house. I even had a neighbor who would come by my house with some regularity asking for a handout to get him by that month. How do you apply what Jesus taught to this context? 

I will confess that the sheer amount of people who wanted a handout was so overwhelming that I got a hard heart after a while. I saw everyone as a grifter, a junkie, a drunkard, or a lazy bum who just wanted me to cut them a check. A lot of them were exactly that, but I needed a come to Jesus moment because I realized after a while that I had no love in my heart for any of these people. 

I wish I could give a one size fits all answer to every situation, but all I can give here is some wisdom. I would encourage you to be both wise and generous in stewarding your resources, however, I would also warn you against making too many excuses to keep you from giving to those in need. And lastly, I think at the end of the day it is better to let someone take advantage of my christlike love, than for me to harden my heart to the needy. God will deal with them in time, either by bringing them to repentance or by dealing with them on the day of judgment. We are just called to be faithful. God will sort it out in the end. It is hard to know what is right to do in every situation, but I do know that the right attitude is to desire the well being of the needy more than the well being of my checking account. 

To walk in this way is not easy, but it is the way of the kingdom. What if we valued the good of others (be they our enemy or the needy) more than we value our dignity, our honor, or even our wealth? Those who embody this radical reversal will find themselves transformed, and I believe, in turn, will transform the world. Again, it is not easy, but it is the way of Jesus. 

III. The Fulfillment of the Law in Love (Matthew 5:43-44)

Jesus, then doubles down on this principle by referencing a common Jewish teaching: "You have heard that it was said, ‘You shall love your neighbor and hate your enemy.’" (Matthew 5:43, ESV). While the Old Testament indeed commanded love for one’s neighbor, "You shall not take vengeance or bear a grudge against the sons of your own people, but you shall love your neighbor as yourself: I am the Lord." (Leviticus 19:18, ESV). Notice, that God’s Law never sanctioned hatred of enemies. The phrase “hate your enemy” was a human addition.

The religious leaders of Jesus' day had distorted God's law, narrowing the definition of “neighbor” to include only fellow Israelites and justifying hostility toward Gentiles. In their interpretation, righteousness was confined to one's own group, leaving room for division, exclusion, and enmity. But Jesus came to unveil a deeper, truer righteousness, a righteousness that transcends human bias and embodies divine love.

However, Jesus' correction is not merely about redefining neighborly love, it is about completely revolutionizing the way we see human relationships. Love, as Jesus presents it, is not transactional. It is not limited by geography, ethnicity, or social status. The religious leaders may have twisted God's command to accommodate human division, but Jesus restores it to its original intent, to reflect the impartial and boundless love of the Father.

In direct contrast to the prevailing teaching, Jesus declares: "But I say to you, Love your enemies and pray for those who persecute you." (Matthew 5:44, ESV). This is one of the most radical commands in the entire Bible. The Greek word for love (agapē) denotes an unconditional, self-sacrificing love. This is a love that seeks the highest good of others regardless of their actions. It is a love not based on emotion but on a deliberate choice to reflect the nature of God.

Loving one’s enemies is an active, intentional pursuit of their good. It is a love that transcends human logic, a love that mirrors God’s own heart.  Jesus provides the ultimate example of this divine love on the cross. As He suffered at the hands of His executioners, He did not curse them. Instead, He interceded for them: "Father, forgive them, for they know not what they do." (Luke 23:34, ESV). In that moment, He revealed the heart of God, a heart that loves even when rejected, that blesses even when cursed, that prays even for those who seek to destroy.

This kind of love is not for the faint of heart. It is a love that requires divine empowerment, a love that cannot be mustered by sheer human will. It demands surrender to God’s Spirit, a daily choice to walk in the way of Christ rather than the way of the world.

To love our enemies is not to condone evil, nor is it to passively endure injustice without wisdom or action. Rather, it is to break the cycle of hatred, to rise above worldly divisions, and to reflect the boundless mercy of our Heavenly Father. It is the hallmark of true discipleship, the distinguishing mark of the kingdom of God.

Jesus does not leave this command in the abstract; He gives us a practical step to embody this divine love: "Pray for those who persecute you." (Matthew 5:44, ESV). Prayer is not merely a way to endure mistreatment. It is a means of transformation, both for us and for those who oppose us. When we pray for our enemies, we invite God to work in their hearts and in ours. We shift our perspective from human justice to divine grace. We relinquish bitterness and embrace the love that changes lives.

Jesus calls us to love as He loves: to extend grace where none is deserved, to pray for those who wish us harm, and to reflect the perfect love of our Father in heaven. This is not an easy calling, but it is the way of Christ, and through Him, it becomes possible.

Make no mistake, this love is not a suggestion; it is a command. It is not theoretical; it is to be lived out in our daily interactions. It is not dependent on how we feel; it is a commitment to act in accordance with the character of God.

IV. Conclusion

As we begin to bring this message to a close, we need to remember that the teachings of Jesus are not meant to remain theoretical ideals but are to be lived out in the real, often harsh, world. Paul echoes Jesus’ teaching in Romans 12:17-21: "Do not repay anyone evil for evil, but give thought to do what is honorable in the sight of all. If possible, so far as it depends on you, live peaceably with all. Beloved, never avenge yourselves, but leave it to the wrath of God, for it is written, ‘Vengeance is mine, I will repay, says the Lord.’ To the contrary, ‘if your enemy is hungry, feed him; if he is thirsty, give him something to drink; for by so doing you will heap burning coals on his head.’ Do not be overcome by evil, but overcome evil with good." (Romans 12:17-21, ESV).

Kingdom living requires a countercultural response to hostility: meeting hate with love, violence with peace, and injustice with righteousness. The world may preach retaliation, but the follower of Christ is called to a higher standard, a standard set by the Lord Himself. Jesus, when struck, did not strike back. When reviled, He did not revile in return. Instead, He entrusted Himself to the One who judges justly (1 Peter 2:23). If we are to be like Christ, then our response to evil must not be to perpetuate it but to extinguish it with the light of God’s goodness.

Jesus concludes this section of His sermon with a high and holy calling: "You therefore must be perfect, as your heavenly Father is perfect." (Matthew 5:48, ESV). At first glance, this command seems impossible. How can fallen, flawed people achieve perfection? However, the Greek word “teleios” means not moral flawlessness but completeness, maturity, and wholeness. Jesus is calling us to grow into the full stature of our faith, to develop a love that mirrors the love of our Father in heaven.

Just as God sends rain on both the just and the unjust, just as He extends grace to those who rebel against Him, so too must we reflect His character in our dealings with others. To be “teleios” is to reach the full potential of our calling, to embody the love that sets us apart as His children. It is to love without boundaries, to forgive without holding back, and to bless even those who curse us.

This maturity is not achieved overnight. It requires daily surrender, daily renewal, and daily commitment to the way of Christ. It means taking up our cross, dying to self, and allowing the Spirit of God to reshape us into the image of Christ (Romans 8:29). It is not an impossible standard but a progressive journey toward divine love.

In the end, radical love is the very heartbeat of the kingdom of God. It is the evidence of genuine discipleship. “By this all people will know that you are my disciples, if you have love for one another.” (John 13:35, ESV). May we then walk in this love, reflecting the maturity of our heavenly Father, and showing the world a glimpse of His kingdom on earth.

May we leave this moment not only as hearers of Jesus’ words but as doers (James 1:22), determined to embody His teaching in our homes, workplaces, and communities. May the world look upon us and see a reflection of divine grace. And may we press on toward the goal of Christlikeness, knowing that “he who began a good work in you will bring it to completion at the day of Jesus Christ.” (Philippians 1:6, ESV).