Flourishing by Following: Retaliation (Matthew 5:38-42)

Introduction  

Today, we explore a passage that challenges the very core of our human nature: our tendency towards resentment and retaliation. How often have we been on the receiving end of a grudge, that silent yet heavy weight of another’s disapproval? You hurt them, and now they are holding it over you. The feeling of being boxed in, unable to shake a negative perception, regardless of our actions, is a painful reality many of us know intimately. I confess, I’ve experienced this firsthand. The frustration of feeling misunderstood, of my efforts to reconcile falling short, is a burden I carry at times.  

And the truth is, as much as we despise being on the receiving end of resentment, haven't we also, at some point, harbored our own grudges? We justify it, perhaps, as self protection; a necessary emotional distance to safeguard ourselves from further hurt. But this “protection” often masks a lack of compassion, a hardening of our hearts. Animosity, left unchecked, breeds unkindness, chilling our relationships and preventing us from experiencing the warmth and fullness of genuine connection. It is against this backdrop of human frailty and fallibility that Jesus offers a radical, counter-intuitive solution: generosity.  

Big Idea: Generosity heals animosity. It is so easy to treat others as they treat us. When someone is unkind, it is difficult to be kind. We are often tempted to fight fire with fire and give people “a taste of their own medicine.” Following this instinct leads to compound pain and injury. Generosity is the key to stopping this cycle.  

Imagine, for a moment, a world without grudges. Picture a society where past hurts don’t define present relationships. Consider how profoundly different family dynamics would be, how business negotiations would proceed, and how marital conflicts would be resolved. Such a world wouldn’t be a naive utopia; it would be a reflection of God's kingdom, a kingdom of peace, reconciliation, and love. Jesus, in Matthew 5:38-42, provides a blueprint for building such a world, one generous act at a time. He lays before us the transformative power of generosity in healing the deep wounds of animosity.  

Passage  

Matthew 5:38-42, “38 “You have heard that it was said, ‘An eye for an eye and a tooth 

for a tooth. ’39 But I say to you, Do not resist the one who is evil. But if anyone slaps you on the 

right cheek, turn to him the other also. 40 And if anyone would sue you and take your tunic, let 

him have your cloak as well. 41 And if anyone forces you to go one mile, go with him two miles. 

42 Give to the one who begs from you, and do not refuse the one who would borrow from you.” 

Misinterpreting the Law  

This passage is one of the parts in Jesus' sermon that is often misunderstood because it is taken out of context. Jesus is not calling for passive submission to evil in all situations. What Jesus is confronting here is the false interpretation of the Old Testament by the Pharisees. This is the fifth time Jesus is correcting the religious teacher's incorrect application of the Law. The four case studies or examples given in verses 39-42 must be understood in the context of the improper application of the Old Testament Law Jesus cited. 

The principle of “an eye for an eye,” drawn from the Old Testament (Exodus 21:24-25; Leviticus 24:20; Deuteronomy 19:21), was intended as a judicial measure to prevent excessive penalties, ensuring that a punishment fit the crime—a principle echoing our modern constitutional prohibitions against cruel and unusual punishment (Eighth Amendment).  

However, this principle was frequently misapplied, becoming a justification for personal vendettas and fueling cycles of revenge. Jesus addresses this misinterpretation directly, demonstrating how it is antithetical to the heart of love that God requires of His people. This law was not meant to sanction revenge or personal vindication; rather, it informed the courts and those in authority on how to determine just punishment.   

The Old Testament itself contains warnings against the pursuit of vengeance (Leviticus 19:17-18). Proverbs 24:29 states, Do not say, ‘I will do to him as he has done to me; I will pay the man back for what he has done.’” Jesus does not intend for a principle meant to govern public order to be used to justify private retaliation. Jesus isn't introducing a new concept; He’s clarifying and deepening an existing moral imperative, just like He has done previously with His teaching on anger, lust, divorce, and oaths. He calls us to move away from a retributive framework and embrace a transformative approach based on generosity and compassion.  

Don’t Resist  

The phrase “Do not resist the one who is evil” can be misunderstood as a call to complete passivity. This interpretation ignores the context, as well as Jesus' own actions and those of the Apostle Paul, who both actively resisted injustice when necessary (John 18:22-23; Acts 16:37; 22:25; 25:8-12). In John 18, Jesus protested when He was slapped by an officer while He was being questioned by the High Priest, Annas. Paul spoke out frequently against the injustice he faced and used his rights as a Roman citizen to prevent himself from experiencing further mistreatment. The resistance that Jesus advocates against is one that stems from a heart consumed by resentment and a desire for retribution. He is speaking against the mentality that says, “You hurt me. Therefore, I can hurt you. I can treat you like you have treated me. Eye for an eye. Hurt for hurt.” Jesus is inviting us to recognize the wisdom of choosing a path that redirects the energy of retaliation into acts of grace. Sometimes, the right or righteous thing to do is to be wronged. There are moments when it is better not to insist on personal rights but rather to comply and even demonstrate generosity. 

Examples  

Jesus illustrates this with four compelling case studies:  

  1. The Slap on the Cheek: Jesus’ instruction to “turn the other cheek” is not about passively accepting physical abuse. Notice how Jesus severely lessened the violence from eye gouging and teeth pulling to being slapped on the cheek. Jesus is not illustrating the endurance of torture but the experience of being insulted. In the cultural context of Jesus’ time, a slap on the right cheek, which would have been performed by a right-handed person with the back of the hand, was an act of profound disrespect, a deliberate humiliation. This was a sign of great disrespect rather than an attempt to use deadly or severe force. Jesus’ response is not about physical passivity but about refusing to engage in the escalating cycle of violence and disrespect. We must read this verse in the context of the misappropriation of the “eye for an eye” principle as permission for personal resentment and negative behavior in reaction to the bad behavior of others. It is a refusal to participate in the “he hit me first” mentality, to relinquish control of our emotions, allowing the other person's actions to define how we respond, but rather choosing a path that refuses to mirror their negativity. It’s a choice to disarm hostility with unexpected kindness. “Turning the other cheek” means leaving yourself open to endure another insult. It’s a choice to allow generosity to heal animosity.  

  1. The Legal Dispute: The instruction to give away one’s cloak after someone has already taken one’s tunic poses a similar challenge. The tunic served as an undergarment, while the cloak was the outer garment, which is more valuable and essential for warmth and protection. The distinction between “tunic” and “cloak” may be overlooked by modern readers. This is akin to Jesus saying to me, “If someone sues you for your Mario Kart graphic t-shirt, give them your Columbia jacket as well.” I cherish my Mario Kart t-shirt, but my Columbia jacket is far more necessary in the Pacific Northwest. Interestingly, the Old Testament law prohibited someone from taking your cloak for humanitarian reasons, as it was utilized as a blanket when sleeping outdoors. We aren't informed if the case is legitimate, but given the context, we must recognize that this legal action is being pursued by an “evil person” (v. 39) or enemy. It is crucial not to misinterpret this passage as implying that we should refrain from resisting someone who attempts to rob us. Such a reading does not align with the context. This isn't about entirely forfeiting one’s legal rights; rather, it encourages a willingness to rise above the adversarial nature of legal proceedings. It emphasizes the choice of reconciliation over resentment, and the act of generously exceeding what is legally required, showcasing a willingness to progress beyond the minimum stipulations of the law toward true reconciliation. I believe Jesus conveys that if an individual you dislike, an “evil” person or enemy, sues you, you should not harbor a grudge and just meet the law's minimum requirements. Instead, you should be ready to respond generously in order to make amends with them as individuals. Compliance will fulfill the law, but generosity could heal the relationship.  

  1. Forced Labor: The term “force” specifically refers to the legal practice wherein Roman soldiers compelled civilians to transport their belongings over a specific distance. This was a disgraceful experience for the Jews. Jesus’ instruction to “go two miles” is not an endorsement of forced labor or a passive posture toward slavery but a powerful demonstration of overcoming resentment. It's about choosing to go beyond the minimum obligation, transforming a forced act into an opportunity to subvert the power dynamic through unexpected generosity. It is a subtle but profound act of resistance through unexpected kindness. This is where we get the common phrase “go the extra mile.”  

  1. Giving and Lending: The final instruction to give to the needy and to lend without hesitation seems straightforward, yet it carries a similar message of generosity toward those who may have previously wronged us. We are not informed whether the begging or borrowing pertains to a legitimate need. It seems reasonable to assume that the need is genuine, similar to the earlier case of a person suing a disciple for his tunic. The individual making the request may be seen as “evil,” but the request itself is not. Jesus is not teaching an unconditional mandate to give to everyone, regardless of their character or need, as Paul clarifies in 1 Timothy 5. In that chapter, Paul illustrates how helping people can, at times, hurt them because it enables and promotes sinful behavior. Also, Jesus did not always comply with every request made of Him. In light of the guiding verses 38-39, which speak against retaliation and revenge, this is a call to examine our motivations when needs arise. Are we withholding generosity out of resentment, or are we giving freely, even when it's difficult? Jesus is speaking against those who would say, “They didn’t help me, so I’m not helping them.” This mindset stems from animosity: Your resentment impacts your generosity.  

Conclusion  

Generosity heals animosity. The common thread uniting these diverse scenarios is the choice to respond to evil not with equal or greater evil but with an unexpected act of generosity. This isn't about being a doormat; it’s about choosing a path that transcends the cycle of animosity, a path that disarms the other person and opens the possibility of reconciliation. It requires wisdom, discernment, and a willingness to set aside our own immediate desires for the sake of a greater good—the restoration of relationships and the breaking down of the walls built by resentment.  

It takes courage to choose generosity when faced with animosity. Sometimes, enduring wrong is the righteous act, especially when it prevents further escalation of conflict. But this is not a passive submission; it's a strategic choice, a proactive decision to disarm hostility. Jesus isn’t asking us to be victims but peacemakers, agents of reconciliation in a world desperately in need of healing.  

Steps  

As followers of Christ, let us commit to asking ourselves in every conflict, “What is the generous thing to do?” Jesus does not command us to be victims but to volunteer to endure evil and respond with compassion and generosity. Therefore, the next time you find yourself in a conflict, whether at work or at home, ask yourself, “What is the generous thing to do?” A good place to start is with your assumption of someone's intentions. While the impact of their actions may be negative, that does not imply their intentions were evil. Assume the most generous interpretation of others' intentions. This approach will significantly change how you react in conflict.  

Maybe you are here today and you are not yet following Jesus. I’m sure imagining a life without grudges may seem unattainable, yet it is the promise of a life transformed by Christ. He offers us the power to overcome our natural tendency toward retaliation. The doorway to experiencing this is Christ. You must come to Him to enjoy this way of living. I invite you to Him today. Only He can give you a heart that is empathetic and generous, rather than reactive and defensive.  

Life Level Application 

Head: Read Luke 6:27-31. How does this passage challenge our natural human inclinations towards revenge and retaliation? How do verses 27 and 31 help us to understand and not exaggerate the examples that Jesus gives in verses 28-30?  

Heart: Read 1 Corinthians 6:1-7. In what situations might “suffering wrong” (v.7) be the most appropriate response to injustice? When might it not be appropriate? How do we discern the difference?  

Hand: Read Romans 12:9-21. What does it mean to “repay no one evil for evil”? How can we “live peaceably with all people” (v.18) in a world often characterized by conflict and division? 

Habit: How do you respond when you are wronged? How can you foster a more generous response? 

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3-Day Bible Reading Plan: “Retaliation”