Uprooting Resentment
Healing The Heart • Sermon • Submitted • Presented
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· 2 viewsLead Pastor Wes Terry preaches a message entitled “Uprooting Resentment” out of Matthew 5:38-42. This message is part of a series entitled “Healing the Heart” and was preached on May 3rd, 2026.
Notes
Transcript
INTRODUCTION:
INTRODUCTION:
Can you imagine a world without resentment?
· a marriage without keeping score of who said or did what when;
· a family dinner that wasn’t stiff and cold;
· a personal friendship not damaged by careless actions;
· a local church where personal avoidance was not common.
How many of the worst seasons of your life would’ve been different if a grudge had never taken root?
How many friendships? How many years of your marriage? How many holidays? How many sleepless nights?
Some of you are still carrying the weight of a personal offense. The name of the offender still changes your mood when you hear it.
A world without revenge and resentment sounds nice. It also sounds completely naive.
Not only does our culture tolerate resentment. It fuels and rewards the power it can have.
We live in a culture that celebrates resentment.
Internet culture and algorithms monetize the rage. The “outrage economy” brings in millions every year.
Political commentary and cable news glamorize resentment. Nothing keeps our attention like an old-fashioned feud.
Comment sections, hot takes, memes and cable news — all of them leverage this enemy to human flourishing.
Human pain, grievance and personal outrage are leveraged and exploited for economic gain.
Age Old Problem
Age Old Problem
They have a powerful influence on every human heart, deployed and disseminated through our cultural incentives.
But let’s be honest. The algorithms did not create this problem. Culture just exploits the power of resentment.
The vice has always lingered in the shadow of our heart.
Before the outrage algorithms, our hearts were keeping score. Long before the timeline was the courtroom of our mind. We silently mastered the art of litigation.
We imagine ourselves in every seat of the courtroom: the prosecutor, the witness, the judge AND the jury. You replay the evidence repeatedly.
You imagine the conversation wherein you win every argument, the injustice of the offense, the guilt of the offender, the scope of the damages and the interest on the debt. You are owed and owed bigly.
You might never say, “I want revenge.” That sounds too ugly. Unchristian. Too honest. So you say it differently: “I hope they know how it feels.” “I hope they get what is coming.”“I’m not bitter — I’m just angry.” “I forgive, but I won’t forget.” “I know it’s not fair, but I must protect myself.”
Sometimes those statements contain genuine wisdom. Sometimes they hide a courtroom for revenge.
Set the Table
Set the Table
That courtroom has a name. The Bible calls it resentment. And it has been killing the human heart from Genesis 3 until today.
But the Bible does not just name the disease — it exposes the source and cures it at the root.
There is a wisdom older and stronger than your offense, and that wisdom is found in the Sermon on the Mount.
What Jesus has to say is at once the most demanding yet liberating thing your heart can ever hear. He offers a better vision for dealing with resentment. His approach leads to a flourishing life.
Even if it were just for a score to be settled, to settle it yourself can do damage to your soul. Resentment and revenge disrupt a life of flourishing.
We’re simply not equipped to set the world aright. That job belongs to God and God alone. When we sit in that seat, it deforms our soul.
Our passage comes from the Sermon on the Mount in Matthew 5:21-48. Jesus does some heart surgery on those who want God’s kingdom..
This Kingdom Righteousness exceeds mere outward compliance. That was the problem with the scribes and pharisees.
Jesus presses deeper: what kind of person are you becoming before God? Six times Jesus says, “You have heard from long ago… but I say to you.” Each one is a portrait of kingdom-righteousness.
So far, we’ve looked at uprooting anger, uprooting lust and uprooting duplicity. Today we’ll examine the problem of resentment. These six illustrations have a purposeful sequence.
The first four deal with what you’re tempted TO DO (murder, adultery and broken promises). The last two deal with what happens TO YOU (insult, grievance, personal loss).
Ultimately, resentment, is a form of sinful pride. It keeps a record of what is owed and will not rest until repaid.
Righteousness requires getting rid of resentment.
Before the score is settled, the debt must be released.
Read the Text
Read the Text
With that in mind lets read our passage.
Matthew 5:38–42 CSB
38 “You have heard that it was said, An eye for an eye and a tooth for a tooth. 39 But I tell you, don’t resist an evildoer. On the contrary, if anyone slaps you on your right cheek, turn the other to him also. 40 As for the one who wants to sue you and take away your shirt, let him have your coat as well. 41 And if anyone forces you to go one mile, go with him two. 42 Give to the one who asks you, and don’t turn away from the one who wants to borrow from you.”
When Jesus uses the phrase “you have heard it said… but I say to you” pattern, He is not contradicting the Old Testament Law. Rather, his teaching, reveals its true intent.
It’s not Moses verses Jesus or wrong versus right. Moses had accurately relayed God’s commands.
The contrast is between “what they heard” and “what God said.” Jesus is revealing God’s original design.
God’s Law was not merely to police our behavior. The Law was given to point us to Jesus. God’s Law reveals the righteousness of God and Jesus is showing what that looks like in real life.
As with the other examples, people misread this passage. That misreading can be dangerous if you're not careful.
People hear these words and think “Jesus was a pacifist.” It’s been used to prohibit defense of any kind.
That’s why some read this text and immediately begin to panic. They say, “Jesus must be joking because this is just not practical.”
Jesus wasn’t joking nor was he a passivist. His words are demanding but they’re NOT unrealistic.
The project of Jesus is to bring abundant life. That life is possessed by a certain kind of person. The person that you are is determined by your heart.
How you respond to offense reveals your heart’s condition.
Which means your reaction to offense reveals your character.
THE ORIGINAL COMMAND:
THE ORIGINAL COMMAND:
Verse 38 opens up like the four examples before. Jesus appeals to an Old Testament Law.
Matthew 5:38 CSB
“You have heard that it was said, An eye for an eye and a tooth for a tooth.”
Most of us have heard that language before. It’s a common slogan for personal revenge.
It’s known as the “lex talionis” or “law of equivalent retribution.”
It shows up at least three different times in the Law of Moses. (Ex 21:23-25; Lev 24:19-20; Deut 19:21)
Exodus 21:23–25 CSB
If there is an injury, then you must give life for life, eye for eye, tooth for tooth, hand for hand, foot for foot, burn for burn, bruise for bruise, wound for wound.
Leviticus 24:19–20 CSB
If any man inflicts a permanent injury on his neighbor, whatever he has done is to be done to him: fracture for fracture, eye for eye, tooth for tooth.
Deuteronomy 19:21 CSB
Do not show pity: life for life, eye for eye, tooth for tooth, hand for hand, and foot for foot.
The Moral Vision
The Moral Vision
Three different books. Three different settings. And in every one of them, the context is judicial.
· Exodus is in the middle of case law about civil injury.
· Leviticus is set in the trial of a blasphemer.
· Deuteronomy is governing the testimony of false witnesses.
It was never applied outside of the court nor did it permit vigilante justice. The lex was a guideline to establish legal justice.
The lex first appeared in the code of Hammurabi (1750 BC). But Babylonian justice had unequal weights and measures. Your wealth would determine the value of your life.
According to Scripture, every human life is equal. Justice, therefore, does not discriminate.
An eye is an eye whether rich or poor, whether priest or a peasant, every life is equal. That alone was a moral revolution.
But the moral improvement went beyond even that.
In a world full of blood-feuds and limitless revenge, lex talionis established moral order.
1. It put resolution in the hands of the court.
2. It capped restitution at proportionality.
The lex talionis was a law of restraint.
God sought to tame human vengeance, not increase its use. It was given as a mercy to protect our hearts from sin.
That moral vision was lost over time. Eventually, the lex became a tool for revenge.
The question stopped being, “what does justice require?” The question had become, “how much vengeance can I take?”
What started as a mercy to encourage restraint become a license to maximize revenge.
Vengeance moved from the courtroom into the human heart. As a result God’s purpose was lost.
Not only was justice thwarted by this change, it actually increased the spread of human suffering.
By establishing a framework of legalized resentment, the souls of men and women were lost in the process.
The rebuke from Jesus addresses that key issue. He was bringing the Lex back to God’s true intent.
The Lex Talionis was never about revenge. It was always a window into Kingdom Righteousness.
THE GREATER COMMAND:
THE GREATER COMMAND:
To bring their attention back to God’s design, he shifts the discussion back to the human heart.
Matthew 5:39a CSB
39 But I tell you, don’t resist an evildoer.
In the original greek there’s a subtle play on words. “Eye for an eye” is literally “eye anti eye.”
Anti is a Greek preposition that means “in return for or in place of.” It’s payback. You hit me, I hit back. Hit-anti-Hit. Force-anti-force. Equal damage. Ledger balanced.
But in verse 39 that same preposition is used, in a way, to stand against itself. “Do not anti-stand the evildoer.” Jesus negates the whole game of “getting even.”
Lex Talionis was a law of restraint. Jesus rebukes its use for revenge.
Jesus uproots the entire engine of resentment.
Misquoting Jesus
Misquoting Jesus
Naturally, this is one of the most misquoted verses in the entire New Testament.
People hear “do not resist an evildoer” and immediately ask the wrong question.
They picture a battered wife, a bullied child or tyrannical regime. They say, “Surely Jesus isn’t telling people just to take it.” That’s right. He isn’t.
We know that because of what the Bible says elsewhere.
We are told to resist the devil (James 4:7).
To stand against the evil day (Ephesians 6:13).
Jesus drove the moneychangers from the temple with a whip (John 2:15).
Jesus cannot mean “no opposition whatsoever.” That would contradict the rest of Scripture.
God’s Word is true and does not contradict. In fact, the context narrows the scope.
Jesus here describes a certain type of offense. They are not violent crimes nor physical abuse. They are personal slights and impositions.
They are wrongs done to you wherein your tempted to wrong back.
Jesus rebukes revenge for relational wrongs.
Do not stand against the wrong-doer in the spirit of retaliation. Do not answer the offense with an offense of your own.
There is a way much greater and more beautiful than revenge. It is the way of righteousness and human flourishing. With that in mind, let’s read the four examples.
Matthew 5:39–42 (CSB)
39But I tell you, don’t resist an evildoer. On the contrary, if anyone slaps you on your right cheek, turn the other to him also. 40As for the one who wants to sue you and take away your shirt, let him have your coat as well. 41And if anyone forces you to go one mile, go with him two. 42Give to the one who asks you, and don’t turn away from the one who wants to borrow from you.
THE COMMAND ILLUSTRATED:
THE COMMAND ILLUSTRATED:
Jesus describes four spheres and four types of offense: personal, legal, political and economic.
These examples are not random but intentionally framed. In every example, the one WRONGED is addressed.
The reason that he focuses on the party aggrieved isn’t because the offender is innocent. (He addresses the “wrong doer” earlier in the sermon.)
His focus on the victim is really for their good. He’s trying make them a certain kind of person. He’s trying to free them from the poison of resentment.
Jesus desires you to have a flourishing life! He knows true life only comes a certain way. Flourishing is found by a certain kind of person. That person possesses a certain kind of heart.
On the question of offense, this is how that heart responds.
It important to read Jesus’ word through that filter.
Otherwise you won’t really hear what he says.
Jesus isn’t saying the offender isn’t wrong.
He’s also isn’t saying that injustice is okay.
The score will be settled and justice will be served. But you’re not equipped to play that role. When you sit in that seat, resentment kills your soul.
For each illustration there’s one common refrain.
Before the score is settled, release what is owed.
With that in mind, let’s read the four examples.
Shamed
Shamed
39 But I tell you, don’t resist an evildoer. On the contrary, if anyone slaps you on your right cheek, turn the other to him also.
The first picture is that of a slap on the right cheek. That Jesus specifies a cheek is instructive for understanding.
Then, as today, most people were “right handed.” The right hand was the working hand and the left was “unclean.”
If I wanted to slap your right cheek with my right hand, I must use the back of my hand. In Jewish culture, a backhanded slap was a form of public shame. It was a way to cause real humiliation.
It was a common thing between a master and a slave, a parent to a child, of someone subservient in some way. If an equal had chosen to backhand your cheek you would right to get angry in response.
This isn’t a barroom brawl. It’s your honor being attacked. It’s when someone attempts to “take you down a notch.”
Which means when Jesus says “turn the other cheek,” he is not telling you to invite physical abuse. He is telling you to “not defend your honor.”
The resentful heart says, “Nobody talks to me like that. I will make them pay.” The kingdom heart says, “My Father knows my name and that’s what matters most.”
Allow the insult to stand and do not respond.
If shamed, resist in-kind response.
Stripped
Stripped
The second picture is a lawsuit of some kind. I’ve put it under the heading of being stripped.
40 As for the one who wants to sue you and take away your shirt, let him have your coat as well.
The word translated “shirt” is the chiton, or inner garment. It was the garment worn next to the skin.
The word translated “coat” is the himation, or outer cloak. It was heavier, more expensive and doubled as a blanket for the poor.
In Old Testament Law, a creditor could legally take a man’s chiton as collateral. But he was NOT allowed to take his himation.
The cloak was protected by Torah because the poor needed it to sleep. (Exodus 22:26–27) So when Jesus says, “let him have your coat as well,” he is telling the disciple to surrender what the law would have protected.
When slapped, don’t respond in kind.
When stripped, give more than they request.
Jesus isn’t advocating careless stewardship. He’s restraining our selfish inclination.
Jeus is saying, “let it go!” Give them what is owed in the eyes of the court and on top of what is taken say, “here’s some more with that.”
The Greek word Jesus uses for “let him have” is the same word he uses elsewhere for “forgive.”
It is the word in the Lord’s Prayer: forgive us our debts. It literally means “let go, release, send away.”
To let go of the cloak is, in Jesus’ own vocabulary, a kind of forgiveness.
Resentment grips. Resentment holds on. Resentment says, “They took something from me, so why should I forgive?”
Without minimizing the loss, Jesus says “stop clinging to what is left.” You so afraid of opening yourself up to greater loss that you’re poisoning your soul with the sin of resentment.
Subjugated
Subjugated
The third picture is a forced mile. Matthew 5:41 “41 And if anyone forces you to go one mile, go with him two.”
In Jesus’ day, Roman soldiers had the legal right to conscript any non-Roman civilian to carry their pack for a mile.
They could pull you off the road, hand you their gear, and march you a Roman mile against your will.
This kind of conscription was bitterly resented in occupied Palestine. It was humiliation under coercive power.
So when Jesus says, “if anyone forces you to go one mile, go with him two,” he is not endorsing servility. He is uprooting the bitter root.
Instead of letting that resentment build up within your heart, after that one mile volunteer one more.
When stripped, give more than they request.
When subjugated, give more than they require.
The first mile is something they’re legalized to take. The second mile is something that CANNOT be compelled.
Resentment protests, “You may control my body, but you will not have my heart.” The kingdom heart says, “You may compel one mile, but I’ll be no slave to bitterness.”
Sought
Sought
The fourth picture is a request for a loan.
42 Give to the one who asks you, and don’t turn away from the one who wants to borrow from you.
This one is less dramatic, but it lands on the same point.
Jesus is not saying you must give every dollar to every person who asks.
The Bible elsewhere teaches the importance of stewardship.
Jesus seems to focus on a loophole often used. It’s the mode of self-protection that we feel when we’re ripped off.
“They took advantage last time so this time I’m DONE.” It is the heart that’s been burned and decides to never give again.
Don’t last past grievance harden your heart. Don’t let past mistreatment close your heart to mercy.
When sought, give without regret.
This specifically applies in the realm of economic but the context of relationship widens out the scope.
Your heavenly Father has unlimited mercy and unlimited supply.
Instead of letting fear drive your heart to self-protection. Let the grace of God drive generosity.
The fact that Jesus ends on something less specific means the posture that he’s after is a heart of mercy-giving.
Don’t turn away. Don’t harden your heart. Don’t let resentment close your open hand.
WHAT JESUS IS NOT SAYING:
WHAT JESUS IS NOT SAYING:
Before we move on, please hear what I’m NOT saying. Jesus is NOT endorsing abuse.
Some of you are hearing these words with wounded ears. You’ve been subjected to mistreatment by those who should protect you.
Turn the other cheek doesn’t mean to take abuse. If there’s abuse of any kind tell someone and we will help.
You can have a loving heart and demonstrate true wisdom. If there’s a danger of abuse then we will get you safe.
1. Jesus is not telling victims to take more abuse.
2. Jesus is not forbidding the pursuit of legal justice.
3. Jesus is not calling evil good.
4. Jesus is not diminishing your pain.
5. Jesus is not excusing your offender.
If you carry those assumptions into these illustrations then Jesus would discourage saving children from abuse. That cannot be true and that should shape your understanding.
Uprooting Resentment
Uprooting Resentment
Whatever Jesus means he is consistent with himself. He’s not restricting legal justice but a heart of resentment.
He’s not denying justice, he relocates where its found.
It’s perfectly fine to hold someone accountable. It isn’t “just fine” to hold onto a grudge.
Four spheres and four ways that others take from us: reputation, property, freedom and goodwill. In every single instance, Jesus says one thing:
Before the score is settled, the debt must be released.
Do not let resentment put down roots within your heart.
Instead, place your offender into the hands of God. He is the only one who puts the world to right.
Entrusting them to God is not moral surrender. It’s actually moral wisdom and better for your soul.
Giving it to God doesn’t mean it wasn’t wrong. It also doesn’t mean the other person will not pay.
The only thing it means is you know you’re not equipped. Justice is too important to try and handle it yourself.
Most of us will crumble should we even try. Give it to Jesus, the just judge of all the earth.
ANGER THAT HAS AGED:
ANGER THAT HAS AGED:
Resentment is just anger with a ledger for keeping score. It is spiritual bookkeeping.
It records every slight. It calculates interest. It replays the tapes.
The slap says, “I am owed honor.”
The lawsuit says, “I am owed repayment.”
The mile says, “I am owed control.”
The request says, “I am owed protection from being asked again.”
The problem with these statements isn’t that they’re false. It’s true that others owe you, but you’ve made that too important.
The moment these desires justify resentment becomes the moment your life jumps off the path to life.
Anger says, “you hurt me.” Resentment says, “you owe me.”
Anger may protest the wrong. Resentment feeds upon it.
You can be angry and seek reconciliation. Resentment rehearses why that would be unfair.
Resentment, once settled, grows within the heart, demanding repayment from those who caused offense.
It shows up in marriage keeping score of who did what.
It shows up in parenting with stubborn thankless children.
It shows up at work with missed promotions and stolen credit.
It shows up in church with unmet expectations.
It shows up in friendship through passive aggression.
It shows up online with algorithms of outrage.
The worst thing about resentment is the lie it sells so well. It sells you a counterfeit vision of flourishing.
The “Good Life” isn’t found by setting the score. The good life is found by releasing the debt.
Do I want justice because I love righteousness? Or do I want revenge because I love being right?
Who do you mentally prosecute when your mind gets quiet?
Whose name changes your mood the moment somebody mentions it?
What story do you keep retelling because it keeps you feeling morally superior?
Where has “wisdom” become a respectable name for a closed heart?
The ugly sin beneath resentment is not just unforgiveness. Resentment is really a form of unbelief.
It is the heart whispering, “if I release this, nobody will care, nobody will see, nobody will make it right.”
JESUS LIVED THE COMMAND:
JESUS LIVED THE COMMAND:
The answer for that fear is to look to the cross. Jesus did not preach what he was unwilling to live.
Look at the four pictures one more time — but this time, watch where Jesus is in the picture.
The same Greek words Jesus used in Matthew 5 show up again in Matthew 26 and 27. Matthew is drawing a line for every reader.
Jesus was shamed but he did not respond.
At his trial, “they spat in his face and beat him; others slapped him and said ‘prophesy to us, Christ. Who hit you?” (Mat 26:67-68)
The Lord who taught his disciples to turn the other cheek offered his own at his trial and crucifixion.
Jesus was stripped but he did not refrain.
“After crucifying him, they divided his clothes by casting lots.” (Mat 27:35) The Lord who told his disciples to release the cloak watched them gamble away his.
Jesus was subjugated. But he did not resist.
“As they were going out, they found a Cyrenian man named Simon. They forced him to carry his cross.” (Mat 27:32) Matthew uses the same Greek word as Matthew 5:41 (angareuō). The Lord who told his disciples to walk a second mile walked the heaviest mile a human being has ever walked.
Jesus was sought but he did not reject.
For the ultimate request. He came, in his own words, “not to be served but to serve, and to give his life as a ransom for many.” (Mat 20:28) The Lord who told his disciples to give to the one who asks gave his life away to the ones who could never repay him.
Before the score was settled, our debt was first repaid.
Jesus gave up everything so we could be redeemed.
Our release is small compared to that of Jesus. We can let them go because Christ has led the way.
Because Christ absorbed our wrongs God’s forgiveness can be granted. Because what Jesus did for us he has also done for all.
Because Christ laid down his life, you can let it go. Turn the other cheek and release what they may own.
The cross is not God permitting injustice. The cross was needed so true justice could be served. Because of Jesus, God can be both just and justifier of any human sinner who puts their faith in Jesus. .
Jesus trusted the father and turned the other cheek. He knew the father had a better path than the way of revenge.
That is the gospel for resentful hearts. Resentment keeps the score. Jesus has paid the debt.
CONCLUSION:
CONCLUSION:
If you have never received the mercy of Christ, you cannot give what you have not received.
Resentment is the disease — Christ is the cure. He came for the angry, the hurt, the wronged, the bitter, the score-keeper. He came for you.
If you have never repented and put your faith in Jesus Christ, today is the day. He is the only way out of the courtroom of your heart, because he is the only one who has paid the bill.
The work of uprooting resentment is not the work of clenching your teeth and trying harder to forgive. It is the work of returning to the cross and believing that the Father sees, knows, and will always judge rightly.
Are you willing to say, “Father, I release my claim to vengeance. I trust you with this person, this situation and this wound. Take the ledger out of my hands and into yours.”
Then take one second-mile step. One step out of the courtroom into the Kingdom of God.
Resentment keeps the score. Jesus has paid the debt.
