
For I tell you that unless your righteousness goes above and beyond that of the scribes and Pharisees, you will certainly not enter the kingdom of the heavens. ~ JESUS (Matthew 5:20)
CORE (The heart of the message):
Now Jesus drops the bomb: real righteousness is different than religious righteousness. Real righteousness is revolutionary in its love, mercy, peace, and compassion. The most religious people are no closer to his kingdom than the worst sinners, maybe even further away, if they are not living lives of love. Jesus leads us into a righteousness that goes above the law to find the love, and goes beyond justice to mercy.
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CONTEXT (What’s going on before and after this passage):
This is the final in our four-part series to help us unpack Jesus’ main thesis in the Sermon on the Mount. After these verses Jesus goes on to provide six illustrations of the point he is making (called the six antitheses). So our understanding of this passage is will become clearer as we keep working our way through the rest of Matthew 5 in our next few studies.
[17] Do not think that I have come to cast down the Law or the Prophets; I have not come to cast them down but to fill them up. [18] For Amen I tell you, until the heavens and the earth pass away, not the smallest letter or even a part of a letter will pass away from the Law until everything comes into being. [19] Therefore anyone who loosens one of the least of these commands and teaches this to others will be called least in the kingdom of the heavens, but whoever practices and teaches these commands will be called great in the kingdom of the heavens. [20] For I tell you that unless your righteousness goes above and beyond that of the scribes and Pharisees, you will certainly not enter the kingdom of the heavens. ~ JESUS (Matthew 5:17-20)
CONSIDER (Observations about the passage):
Righteousness. As discussed in an earlier study, “righteousness” is a different biblical word and idea than “justice”, even though the two are often confused, conflated, and equated by uninformed or linguistically sloppy Christians. Real righteousness is right-relatedness, which includes and even centralizes grace, mercy, and peace. Real righteousness is not sinlessness but wholeness, individually and relationally. For instance, a disciple who obeys the Sermon on the Mount to perfection will be someone who prays daily for forgiveness of their sin, deals with the plank in their own eye, and who regularly grants non-judgemental mercy to others who sin so they themselves will receive mercy. For Jesus, the ethical goal for the Church is not moral perfection but mercy perfection (compare Matthew 5:48 with Luke 6:36). Here as elsewhere, Jesus radicalizes our idea of righteousness. Radical righteousness goes above and beyond religious righteousness: above the law to love and beyond justice to mercy. The illustrations Jesus gives later in Matthew 5 will help us see that one can claim to keep the letter of the law and yet be guilty of breaking the spirit of the law. For instance, someone might claim to have avoided murder and adultery (“I’m better than King David!”), and yet still be a murderer and adulterer in their heart (“Whoops. Spoke too soon.”).
Above and beyond. The two Greek words used here mean a) “more than” or “greater than”, used to describe how something “greater than” the wisdom of Solomon is found in Jesus (Matthew 12:42), plus b) “surplus” or “over and above”, used to describe the “leftovers” from Jesus’ miraculous loaves and fishes lunches (Matthew 14:20; 15:37). The righteousness of Jesus people must be over and above, or above and beyond that of the scribes and Pharisees. This kind of righteousness is less concerned with sin avoidance (which is still important) and more focused on actively engaging the world around us with compassion. In the words of Anabaptist theologian Stanley Hauerwas in his commentary on the Gospel of Matthew: “The community that Jesus calls into existence cannot be determined by what it avoids.”
The scribes and Pharisees. The scribes were professional teachers of the law, sometimes called “lawyers” in older translations. They were the Torah scholars who had been in training since childhood. The Pharisees were a fundamentalist movement of “back to Bible basics” who wanted everyone to follow the Law of Moses meticulously. These two groups of Jewish religious leaders made up the best and brightest in Israel and were the most punctilious (I like that word) in keeping the law. And Jesus says, we need to be more righteous than them? In fact, later when rebuking the Pharisees, Jesus tells them that because they have not changed their hearts, even though they may keep the letter of the law in their lifestyles, they are still “lawless” (Matthew 23:28). For Jesus, the heart of the matter is always the human heart.
Certainly not. There are two different Greek words for “no” or “not” and Jesus (as recorded by Matthew) uses both here (translated as “certainly not” which flows better than “not not”). Unless our righteousness goes above and beyond the religious leaders, we will “no no, never never, uh uh uh” enter the kingdom of the heavens.
The kingdom of the heavens. Remember that for Jesus, the kingdom of the heavens is both an eternity with God AND heaven coming to earth right here and right now. Jesus is teaching us about more than eternal salvation after we die – he is teaching us about being in tune with his kingdom of love while we’re still alive. When we prioritize religious law and justice over relational love and compassion, we are missing the kingdom of heaven all around us. The Pharisees among us, like the older brother in the Parable of the Prodigal son, are standing outside of what God is doing.
As the sermon progresses, we realize that Jesus did not expect his disciples to surpass the scribes and Pharisees at their own game; rather, he redefined righteousness. ~ Daniel M. Doriani (Matthew)

Jesus says our righteousness must go above and beyond that of the scribes and Pharisees.
CONFESSION (Personal reflection):
I confess that the way of law has a kind of simplistic appeal to my religious mind. It is straightforward and easier to comprehend. Specific sins, for instance, had specific punishments in the days of Moses, end of story. I for one would have been stoned to death by now, and even if that feels harsh, it has a kind of stamped-it-no-erasies clarity to it that I sometimes find appealing. Mind you, Jesus kind of threw a monkey wrench into that system of justice with his whole “whoever is without sin should cast the first stone” maneuver (John 8:7). Way to muddy the waters Jesus. (Or, did he suddenly make everything more clear?)
The way of grace that Jesus brings is more messy. His atonement erases sin and his love is all about second chances – even seventy times seven chances. (See our discussion about Jesus and Peter in our Coal Fire Fellowship study.) Sinners just live longer in the New Covenant (unless your names are Ananias or Saphira). And we have to learn how to deal with one another, as increasing numbers of us fail and hopefully repent and are granted fresh starts rather than are stoned to death.
The way of grace sacrifices some clarity and structure in favour of relationship. This will be appealing to some and frustrating to others. The way of grace means some questions have to be answered by working issues out in real time, in real life, case by case, face to face. The way of grace is less about consulting the rule book and case law and more about walking in wisdom that dares to get intimately involved in people’s lives. The way of grace might seem inconsistent on the outside by anyone who isn’t intimately engaged with the hearts of the people involved, but love cares less about appearing consistent and more about being compassionate. In the words of Ralph Waldo Emmerson, “A foolish consistency is the hobgoblin of little minds.”
For instance: should a pastor who has morally failed in a significant way ever return to pastoring? (I’m asking for a friend.) The way of Law would make this a simple issue: stone the adulterers and move along. The way of grace leaves us with questions, and a variety of possible answers since the New Testament Scriptures don’t give a hard-and-fast rule. Some say a failed pastor should never return to ministry, and others say yes, they can, after a specific timeframe and process of healing. In this second group, some say as little as six months away from ministry is the appropriate time for a failed pastor to work on healing and wholeness, while others say one-to-two years is best (probably the most common position). Still others say any restoration process should be more like five-ten years. And in the “never” group, some say an alternative form of ministry aside from pastoring is allowable (teaching, writing, missions, etc.), while others say secular employment is their only allowable way forward.
What do you think?
I’ll go first… I don’t know. I am on a journey of listening to opinions and insights as I assess my life – past, present, and future. (Prayers appreciated!) But one thing I do believe with clarity: the best decisions happen via case-by-case assessment made by wise and mature believers who are intimately engaged with the person and the process. We cannot “gently restore” someone caught in a sin (Galatians 6:1) without journeying closely with them to observe and engage them with discernment, accountability, and compassion. Qualities like genuine repentance, humility, and submission to accountable input are hard to discern from a distance. This means all moral pontificating from far away can be laid to rest. Saints have better ways to invest their God-given energies.
Pastoral career restoration debates aside, what is far more important is this: restoration as family, as sisters and brothers, is always paramount for the Church as a heavenly kingdom community.
And this issue is just one of many that, under the New Covenant, we need to fill the gaps with grace. We should accept that good and godly sisters and brothers will hold different positions (and will think they have Scriptural guidelines and Holy Spirit leading on their side).
The way of law (over liberty) and justice (over mercy) will always be appealing to religious folk, but we must go above and beyond the righteousness of the scribes and Pharisees if we want to live the life of heaven here and now.
COMMENTARY (Thoughts about meaning and application):
Many scholars agree that we are talking about Jesus’ most shocking statement in his entire sermon, because the scribes and Pharisees were the epitome of righteousness in first-century Israel.
The Holy Spirit is helping Jesus create a movement of disciples who are “oaks of righteousness, a planting of the LORD for the display of his splendor” (Isaiah 61:3). But the “righteousness” he has in mind is not of this world.
In many places, the apostle Paul reinforces what Jesus is teaching in the Sermon on the Mount. Here is one of those passages [with explanatory notes in square brackets]:
No human being will be justified [the verb form of righteous – righteousified] in his sight by observing the law; for through the law comes consciousness of sin. But now [one of the biggest “buts” in the Bible!] the righteousness of God has been manifested apart from the law, though testified to by the law and the prophets, the righteousness of God through faith in Jesus Christ for all who believe. For there is no distinction; all have sinned and are deprived of the glory of God. They are justified [made righteous] freely by his grace through the redemption in Christ Jesus, whom God set forth as an expiation [meaning the one who wipes our sin clean away], through faith, by his blood. ~ The apostle Paul (Romans 3:20-25, New American Bible, Revised Edition, italics mine)
This new righteousness is a gift of grace from God, who forgives our sin, cleansing it away completely (the meaning of “expiation”). What Good News! When we practice mercy and forgiveness toward the sin of others, we are in tune with the real righteousness of God. (And if you find it hard to practice mercy and forgiveness, take time to ponder how much God has forgiven you.)
Notice Paul’s opening statement: no human being will be made righteous by observing the law. Whoa. Paul is saying that even IF someone observes the law perfectly, that isn’t enough to make someone truly righteous inside-out. A perfect law-abiding person has graduated to the level of a religious legalist – good for them – but they are not yet lovingly righteous. We can perform all of the right actions, but if our morality is not motivated by love, those good deeds are just performative noise (1 Corinthians 13:1-4).
[EXCURSUS – EXPIATION VS PROPITIATION: Caution, this is a total Bible nerd paragraph – feel free to skip ahead. You’ll notice in the translation of Romans 3:25 above that Jesus is called our “expiation”. The translators offer this note… “This rendering is preferable to “propitiation,” which suggests hostility on the part of God toward sinners. As Paul will be at pains to point out (Romans 5:8-10), it is humanity that is hostile to God.” The Greek word here is hilastérion, meaning the “mercy seat” (as it is translated in Hebrews 9:5). It is the place of mercy where our sin is wiped away, rather than the place of judgement where God’s wrath is wiped away (the meaning of propitiation). The emphasis here is on wiping away our sin, not wiping away God’s anger. The sacrifice of Christ changes us, not God. God didn’t pour out his wrath upon Jesus, we poured out our wrath on Jesus, and God forgave us anyway, for “God was in Christ, reconciling the world to himself (2 Corinthians 5:19).]
When we accept this inside-out cleansing righteousness of God, we are rightly robbed of all moral boasting about our successes (shame about our failure). Paul says, “Then what becomes of boasting? It is excluded. Through what kind of law? That of works? No, rather through the law of faith” (Romans 3:27). Paul is fond of law-based word-plays (e.g., Romans 7:21, 23; 8:2). He knows that the Greek word for law (nómos) can be used to mean principle or standard. So Paul says the Law of Moses has been replaced with the “law” of faith, which is really not a law at all, but a trusting relationship.
The scribes and Pharisees were the social justice movement of their time. But Jesus says his disciples must go beyond joining a social justice movement to forming a social mercy movement. This is real righteousness.
Please note: Grace and mercy are not presented by Jesus as provisions for our failures to be righteousness; in the New Covenant, grace and mercy are how God defines righteousness! You don’t have to be morally perfect to be righteous. You just have to be graciously compassionate and merciful toward yourself and others in the face of moral failure. That is real righteousness.

This is not the motto of the Kingdom of the Heavens, which would be closer to “NO MERCY, NO PEACE.”
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A final thought about how all of this affects our approach to reading the Bible.
Jesus is teaching us a process of interiorization, as the prophets predicted would be the nature of the New Covenant (Jeremiah 31:31-34; Ezekiel 11:19; 36:26-27; Hebrews 10:16). God has always valued the interior over the exterior (e.g., 1 Samuel 16:7; Psalm 40:6-8; 51:16-17; Hosea 6:6) – after all, the same God is behind both Old and New Covenants – but under the New Covenant God finally moves us into the way of relating that has always been closer to his heart.
According to God, grace is more true than law, since law-compliance can be coerced with the right promises of reward and threats of punishment without any heart-to-heart caring or connection.
For the law was given through Moses; grace and truth came through Jesus Christ. ~ The apostle John (John 1:17)
Notice also that the law was “given” – like a gift that is presented at arms length. But grace and truth “came” – they are values embodied in PERSON, the person of Jesus. Jesus claims to do more than TEACH Scripture’s true meaning and purpose. Jesus claims to BE Scripture’s true meaning and purpose.
What does this mean practically regarding our Bible reading together? The answer lies in the rest of Matthew 5, where Jesus will give us six examples of how to and how not to read Scripture. We will see that two guidelines emerge. Reading the Bible as fulfilled in and by Jesus will mean:
1. GOING WITHIN. We find the internal meaning of a law, command, or rule. For instance, do not murder becomes do not be angry with someone or even disrespect them, and do not commit adultery becomes do not look with lust. So although we may be released from the letter of the law, we still find guidance from the principle embedded within each precept, the love embedded within the law. (This is called “principlism”.)
2. GOING BEYOND. We see how Jesus puts an end to a temporary law, command, or rule because his way of love overrides the way of law. For instance, Jesus overrules the lex talionis – eye for eye, tooth for tooth – in favour of non-retaliatory enemy love. Jesus also overrules the Mosaic laws on divorce (tightening, not loosening them) as well as the Torah’s teaching about swearing oaths. Some Christians are uncomfortable with this – if God has said something once, they reason, it must endure forever. But this is silly. The Law of Moses was given to a specific people (Israel) for a specific time (until Christ came). And now Jesus is giving a new love ethic that will be for all people everywhere always. Later Jesus cancels dietary laws (Mark 7:19) and the early Church used this approach to discern that they were fully released from the entire Old Testament Law, including the law of circumcision (e.g., Acts 15; Galatians 5).
This is how Jesus helps us find wisdom and joy in every verse of the Bible. We do not tear out our Old Testaments, but we do read them differently, as already fulfilled Scripture.

CONCLUSION (One last thought):
Real righteousness, the inside-out life of love, is more messy than the outside-in life of law. The Spirit-led life requires space and patience to learn over time, to make mistakes and receive and give mercy, to exercise our hearts through trial and error and failure and forgiveness and brokenness and restoration, and to learn to discern the voice of the Spirit over the cacophony of competing voices in our lives. The way of law produces immediate clarity and compliance, yes, but heart-change is optional and eventually becomes irrelevant. The way of love, which is the way of real righteousness, is the way of living in the kingdom of Christ.
Dear Jesus, please give us real eyes to realize where the real lies.
CONTEMPLATE (Scripture passages that relate to and deepen our understanding of this topic):
1 Samuel 16:7; Psalm 40:6-8; 51:16-17; Jeremiah 31:31-34; Ezekiel 11:19; 36:26-27; Hosea 6:6; Matthew 5:21-48; John 1:16-18; Romans 3:20-31; 1 Corinthians 13:1-8; Hebrews 10:14-23
CONVERSATION (Talk together, learn together, grow together):
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What is God revealing to you about himself through this passage?
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What is God showing you about yourself through this passage?
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What has been your pattern of Bible reading, if at all? Has anything helped motivate you to get into the good book?
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What is one thing you can think, believe, or do differently in light of what you are learning?
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What questions are you still processing about this topic?
Thank you for reading. Bless you!