Introduction

• Jesus develops—and gives to the world—radical people.
• Reminder: Six examples of how Jesus fulfilled the Law and the Prophets, and promoted a deeper righteousness than the scribes and Pharisees.
  • Our first three: anger, lust, divorce.
  • Our next three: vows, revenge, enemies.
• Interpretive work:
  • None of our interpretations of what Jesus said should lead us to ridiculous, impossible, or contradictory conclusions.
  • Nor should they lead us to dismiss Jesus and his words.

1. Radically Trustworthy (5:33-37)

• Jesus wants to develop—and give to the world—radically trustworthy people.
  • Definition: kingdom citizens are consistently honest, reliable, and trustworthy, to the point that oaths aren’t necessary—they keep their word.

33 “Again you have heard that it was said to those of old, ‘You shall not swear falsely, but shall perform to the Lord what you have sworn.’ 

Old Testament Quotation

A mash-up of passages.

• You shall not swear by my name falsely, and so profane the name of your God: I am the Lord. (Leviticus 19:12, ESV)
  • Numbers 30:2, Deuteronomy 23:21, etc.
• Jesus may have even had the third commandment—you shall not take the Lord’s name in vain (Ex. 20:7)—in mind.

Why did the Old Testament say it?

• Restrict and control the chaos of deception—too much lying and too many oaths.

Others’ Interpretation

• The religious leaders of Christ’s day had developed elaborate rules that enabled people to evade the binding nature of oaths.
  • To swear by God’s name was considered totally binding.
  • To swear by heaven, the earth, or Jerusalem, rather than God’s name, meant their oaths weren’t binding.

34 But I say to you, Do not take an oath at all, either by heaven, for it is the throne of God, 35 or by the earth, for it is his footstool, or by Jerusalem, for it is the city of the great King. 36 And do not take an oath by your head, for you cannot make one hair white or black. 37 Let what you say be simply ‘Yes’ or ‘No’; anything more than this comes from evil.

Jesus’ Teaching

• God is God over heaven (it’s his throne), the earth (it’s his footstool), and Jerusalem (it’s his city)—it all belongs to him (34-35)!
• Come to think of it, his jurisdiction extends to your head—you can’t even change your hair color (36)!

Some Little Steps

Jesus:

• Don’t swear falsely (33).
• Don’t take an oath at all (34-36).
• Let what you say be simply ‘Yes’ or ‘No’ (37).

What this doesn’t mean:

• Ridiculous interpretation: never make a contract, sign a document, vow during a wedding, or testify in court.
  • Impossible/Impractical: you have to enter into agreements in this life.
  • This wasn’t their problem. They were essentially lying with their oaths. The problem was this elaborate system which made them all rather untrustworthy. So an oath as we know it is fine, if you are actually trustworthy in it.
• Contradictory interpretation: there are godly oaths throughout the entire Bible.
  • Paul regularly used oath-like language—calling God as his witness (Rom. 1:9; 2 Cor. 1:23).
  • Jesus Himself responded when placed under oath before the Sanhedrin (Matt. 26:63–64).
  • And God Himself takes oaths throughout Scripture (Gen. 22:16; Heb. 6:17).
• Legalistic interpretation: you can never change a plan.
  • Paul was hammered by the Corinthians for changing his stated plans (2 Cor. 1:16-24).
  • James advised against the pride of acting as if our plans are concrete—we don’t know what tomorrow will hold (James 4:13-16).

What it means:

• Jesus wants to develop—and give to the world—radically trustworthy people.
• Definition: kingdom citizens are consistently honest, reliable, and trustworthy, to the point that oaths aren’t necessary—they keep their word.
  • This is about integrity.
    • Be someone who is expected to be trustworthy—an oath is not sought after from you!

Application: the disciple should be a trustworthy person in every sphere.

• Sayings: We’ll see, maybe, I’ll pray about it, I’ll think about it.
• Workplace: Colossians 3:22–24—work heartily as for the Lord, not for men.
• Friendships: Don’t be a flake.
• Church: If you sign up to serve or give, follow through.
• Family: Be dependable; honor marriage vows.
• To the Lord: Ecclesiastes 5:4—”When you vow a vow to God, do not delay paying it.”

2. Radically Surprising (5:38-42)

• Jesus wants to develop—and give to the world—radically surprising people.
  • Definition: kingdom citizens are surprising in their response to personal insults and infringements because they are secure in their standing before God.

38 “You have heard that it was said, ‘An eye for an eye and a tooth for a tooth.’ 

Old Testament Quotation

Various Passages

• 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)
  • Repeated in various forms (Lev. 24:20; Deut. 19:21).

Why did the Old Testament say it?

• This was designed to control anger and violence and keep God’s people from revenge and retaliation. It did this in 2 ways:
  • 1. Removed retribution from the offended party, instead giving it to the judges.
  • 2. Limited the punishment to fit the crime (in the form of an equivalent payment/fine/restitution).

Others’ Interpretation

• What did the religious leaders say?
  • 1. They took back the responsibility from the judges, making the Law into a personal license for revenge.
  • 2. They made retaliation a duty to perform, which created a vendetta mentality.

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.

Jesus’ Teaching

• Radical responses—cheek, cloak, two miles, give.
• Jesus dips into the hyperbolic to make his points—a hyper-literalist approach to this passage would surely leave us naked and unhoused in no time.
  • Not civil—as in no police or self-defense.
  • Not national—has nothing to do with state-based relationships (Romans 13, 1 Peter 3).
  • Not ridiculous—we can protect children, escape an abusive situation, fight for justice, close a bank account, say no to an addict who asks for more money, etc.
  • Not impossible—we must defend our families or loved ones.
  • Not mechanical—know the spirit of what Jesus is saying.
  • Not contradictory—
    • Resist the devil, and he will flee from you. (James 4:7)
    • Note: Even Jesus objected when struck unjustly at his trial (John 18:22–23). Even Paul appealed to his legal rights when beaten illegally in Philippi (Acts 16:37) and when threatened in Jerusalem (Acts 22:25).
    • The objection is not off-limits. What is forbidden is the self-vindicating, honor-protecting, score-settling drive to get even.
  • Note: I will resist the interpretive wars regarding this, and many of the other, exhortations from Christ found in Matthew 5. I will say, I don’t believe we should immediately dismiss his teachings by downgrading their reach, but I also believe they are extreme illustrations designed to shatter self-centeredness and position us towards radical generosity and non-retaliation.
• The spirit of Jesus’ teaching: kingdom citizens are surprising in their response to personal insults and infringements because they are secure in their standing before God.

Some Little Steps

• Surprising people: all four examples of response are surprising.
  • Turn to him the other cheek (39)—a surprising response to personal insults.
    • A slap on the right cheek, delivered by a right-handed person, is a backhanded blow, not a fighting punch. It is a public insult—a deliberate act of humiliation, like being spat upon.
    • This is about honor, not physical safety.
  • Let him have your cloak as well (40)—a surprising response to the infringement of personal rights.
    • Someone sues you for your inner garment, your tunic. Jesus says: give them your cloak as well.
    • This is startling because the cloak was legally protected under biblical law—no creditor could take it, because the poor used it as bedding (Ex. 22:26–27).
  • Go with him two miles (41)—a surprising response to the inconvenience of eroded personal liberty.
    • Roman soldiers had the legal right to compel civilians to carry their equipment for one mile. It was resented as a visible, daily symbol of occupation and humiliation (i.e. Simon, Matt. 27:42).
  • Give, and do not refuse, beggars and borrowers (42)—a surprising response to request for personal generosity.
• Exhortation: We must allow the strength, awkwardness, and challenge of Christ’s words to sink in.
  • Example: “Do not kill them,” he answered. “Would you kill those you have captured with your own sword or bow? Set food and water before them so that they may eat and drink and then go back to their master.” (2 Kings 6:22)
  • Example: Lighthouse vs. Vending machine
• We can only surprise in life if we are secure in our identity.
  • The insulted believer knows who they are to the Father.
  • The infringed upon believer knows the One who laid down his rights.
  • The inconvenienced believer knows the Lord who went beyond the extra mile.
  • The entreated believer knows the God who will provide.

3. Radically Loving (5:43-48)

• Jesus wants to develop—and give to the world—radically loving people.
  • Definition: kingdom citizens love with the same radical and indiscriminate generosity as God himself because he, not the recipient, is the source of their love.

43 “You have heard that it was said, ‘You shall love your neighbor and hate your enemy.’ 

Old Testament Quotation

The Summary Passage

• 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)
• They were called to be a kingdom of priests and a holy nation (Ex. 19:5-6).

Others’ Interpretation

• The phrase “hate your enemy” is not found in the Old Testament, but was the conclusion they’d come to over time.
  • The religious leaders had come to believe your neighbor was a reference to fellow Israelites. They also came to the conclusion that hatred for the Gentile world was their duty.
  • In Jesus’ day, this inference had become the standard interpretation in some groups.
    • The Qumran community—the sect that produced the Dead Sea Scrolls—vowed “to love all the sons of light and hate all the sons of darkness” (1QS 1:3–4).

44 But I say to you, Love your enemies and pray for those who persecute you, 45 so that you may be sons of your Father who is in heaven. For he makes his sun rise on the evil and on the good, and sends rain on the just and on the unjust. 46 For if you love those who love you, what reward do you have? Do not even the tax collectors do the same? 47 And if you greet only your brothers, what more are you doing than others? Do not even the Gentiles do the same? 48 You therefore must be perfect, as your heavenly Father is perfect.

Jesus’ Teaching: our good treatment of others is not contingent on their good treatment of us.

• Love your enemies
• Pray for those who persecute you

Some Little Steps

Be a cut above the unbelieving world.

• Tax collectors—think payday loan operator who charges 400% interest or a local politician who reverses the campaign promises and hurst the local community—love those who love them (46).
• The Gentiles—think people groups from the nations who don’t know even the elementary things of Scripture or God—greet their brothers (47).

Imitate your Father in heaven.

• He gives the resource of the sun to evil and good people alike (45).
• He gives the resource of rainwater to the just and the unjust alike (45).
  • Theologians: common grace—God is indiscriminate!
  • Example: Imagine God boycotting people! He is indiscriminate with the sun and rain.
• Radical Love: the motivation of this love is (1) our high calling as Christ’s people and (2) the character of the Father, not the worthiness of the recipient.

Be perfect like your heavenly Father is perfect (48).

• A stunning end to this portion of the sermon.
• Jesus did not mean we must become morally flawless.
  • Obvious: All have sinned and fallen short of God’s glory (Rom. 3:23).
• Jesus used a Greek word—teleios—that means whole, complete, and fully mature.
  • God’s love is perfect, both in its breadth (who it includes) and its depth (how far it goes for each person).
• Jesus meant we should pursue a godly wholeness in our character.
  • In our love.
  • But also in all the categories he addressed in these six movements—our response to offenses, our commitments to others, our marital covenants, our treatment of human sexuality, the temptation to harbor anger. And more!
• A stirring that never fades:
  • Create in me a clean heart, O God, and renew a right spirit within me. (Psalm 51:10, ESV)
  • Blessed are those who hunger and thirst for righteousness, for they shall be satisfied. (Matthew 5:6, ESV)

Conclusion

• It is inevitable—if we are reading and studying this correctly—that we feel a sense of shortcoming, a need for grace.

• • • So we must focus afresh on Christ.

• Christ is:

• • • Radically trustworthy—he said “yes” to the Father and fulfilled his purpose.
    • Radically surprising—he went way further than the second mile at the cross.
    • Radically loving—he prayed for his persecutors as he died for the whole world.

• When Christ comes into your life, he begins to transform you.

• • He aims to make you like himself.
  • The gospel is meant to go incredibly far in our lives!

Study Questions

Head (Knowledge & Understanding)

1. Jesus quotes the Old Testament law “an eye for an eye and a tooth for a tooth” — but this law was never intended to license personal revenge. What were the two original purposes of this law, and how had the religious leaders of Jesus’ day distorted it into something the law never intended?
2. In Matthew 5:48, Jesus commands his followers to “be perfect” as the heavenly Father is perfect. What does the Greek word teleios actually mean, and how does understanding that word change the way you hear this command?

Heart (Feelings & Impressions)

1. Nate described kingdom citizens as “radically surprising”—people whose response to insult, injustice, and inconvenience catches others off guard because they are secure in their identity before God. When you are insulted or wronged, what does your gut-level instinct reveal about where your sense of security is actually rooted? What does your first reaction tell you?
2. The sermon pointed out that “hate your enemy” was never in the Old Testament—it was a conclusion people arrived at over time, codified by groups like the Qumran community who divided the world into “sons of light” and “sons of darkness.” Is there a person, group, or category of people in your life that you have quietly placed in an “enemy” category? What does it feel like to sit with Jesus’ command to love and pray for them?

Hands (Actions & Commitments)

1. Pastor Nate applied “radically trustworthy” across five spheres: the workplace, friendships, the church, family, and your relationship with God. Which of those five spheres is where your “yes” is least reliable right now—where your word costs you the least to give and the most to keep? What is one concrete step you could take this week to close that gap?

Jesus gives one practical entry point into enemy love: prayer. Not prayer that God will change the other person, but intercession on their behalf — praying for their genuine good and flourishing. Identify one person you find it genuinely difficult to love. Commit to praying for them specifically every day this week — not for them to change, but for God to bless them. Come back next week ready to share what happened in your own heart.