A Greater Righteousness (1)

The Kingdom of GOD  •  Sermon  •  Submitted   •  Presented   •  51:22
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Announce text: Matthew 5:17-20
Key Text: Matthew 5:17-20
Review
play BP review: cartoon (6:34) or visual commentary (10:12)
We’re in a series on the KINGdom of GOD, and as we have progressed through this series, we have arrived at JESUS’ famous SOTM. The review we just saw covered JESUS’ introduction which included the Beatitudes. We are now arriving at the next section of the SOTM, and this section I have chosen to title, A Greater Righteousness - Torah & Prophets. So, this will be the overarching title or theme for the next subset of messages covering Matthew 5:17-48.
This morning, we will be focusing on vv.17-20, so for the sake of time, I am not going to read vv.17-48. Instead, I will back up to last week’s passage and then follow it with today’s passage to provide a little more context.
Announce text again: Matthew 5:17-20

Scripture Reading

Matthew 5:14–20 NASB95
14 “You are the light of the world. A city set on a hill cannot be hidden; 15 nor does anyone light a lamp and put it under a basket, but on the lampstand, and it gives light to all who are in the house. 16 “Let your light shine before men in such a way that they may see your good works, and glorify your Father who is in heaven. 17 “Do not think that I came to abolish the Law or the Prophets; I did not come to abolish but to fulfill. 18 “For truly I say to you, until heaven and earth pass away, not the smallest letter or stroke shall pass from the Law until all is accomplished. 19 “Whoever then annuls one of the least of these commandments, and teaches others to do the same, shall be called least in the kingdom of heaven; but whoever keeps and teaches them, he shall be called great in the kingdom of heaven. 20 “For I say to you that unless your righteousness surpasses that of the scribes and Pharisees, you will not enter the kingdom of heaven.
Prayer for added blessing to the reading of the Word

Message

In the Antarctic summer of 1908-9, Sir Ernest Shackleton and three companions attempted to travel to the South Pole from their winter quarters. They set off with four ponies to help carry the load. Weeks later, their ponies dead, rations all but exhausted, they turned back toward their base, their goal not accomplished.
Altogether, they trekked 127 days. On the return journey, as Shackleton records in The Heart of the Antarctic, the time was spent talking about food -- elaborate feasts, gourmet delights, sumptuous menus. As they staggered along, suffering from dysentery, not knowing whether they would survive, every waking hour was occupied with thoughts of eating. Jesus, who also knew the ravages of food deprivation, said,
"Blessed are those who hunger and thirst for RIGHTEOUSNESS." We can understand Shackleton's obsession with food, which offers a glimpse of the passion Jesus intends for our quest for righteousness.
Source Unknown.

Introduction

Big Idea: The true righteousness required for the KINGdom of heaven is found in a relationship with JESUS, surpassing mere human standards and reflecting HIS perfect character.
JESUS taught that the true guide for right living—GOD’s Wisdom—is contained in the Hebrew Scriptures, the Torah and the Prophets. HE asserted that HE was uniquely advancing the narrative of those Scriptures, demonstrating what genuine righteousness looks like and how to embody GOD’s Wisdom in everyday life.
Let’s read today’s text again by itself.
Matthew 5:17–20 NASB95
17 “Do not think that I came to abolish the Law or the Prophets; I did not come to abolish but to fulfill. 18 “For truly I say to you, until heaven and earth pass away, not the smallest letter or stroke shall pass from the Law until all is accomplished. 19 “Whoever then annuls one of the least of these commandments, and teaches others to do the same, shall be called least in the kingdom of heaven; but whoever keeps and teaches them, he shall be called great in the kingdom of heaven. 20 “For I say to you that unless your righteousness surpasses that of the scribes and Pharisees, you will not enter the kingdom of heaven.
So, as we were reminded in our review, we have been traversing the SOTM, and we just finished JESUS’ introduction to this sermon. Today, we begin the transition from introduction to the main body - the message of JESUS’ SOTM. In the Beatitudes, we saw the surprising states of being that JESUS defined as the good life. We learned about the kind of people JESUS was forming as citizens of and are at home in the KINGdom of GOD. We also learned there is a cost and a reward for citizenship: we should expect hardship, but everlasting peace is coming. Finally, we saw how JESUS concluded HIS introduction by describing how HE envisioned the citizens of the KINGdom would look like as Image-bearers in the world.
This morning, we will see that JESUS begins the first big turning point in the structure of HIS sermon were HE begins to speak to the application of what HE has been describing and teaching to this point. How can HIS followers be the salt of the earth, the light of the world, and a city on a hill? How can we fulfill the covenant GOD established with humanity? What does it look like to do peacemaking? What does it look like to live this way?
The word used by JESUS to describe this way of life, is the word righteousness (tzedekah). As we were reminded earlier, righteousness means doing right by GOD and others.
How can we live righteously? JESUS is going to tell us that if we want to know how to do right by GOD and others, we need to study the Torah because it is only by following GOD’s commands that we can live righteously; and it is only by studying and meditating on HIS Scripture that we can learn HIS Wisdom and know how to apply it to our lives.
The title for today’s message is ...

Righteousness Redefined: The Key to the Kingdom

In our text this morning, there are four movements in the statements JESUS is making. There is a lot going on here, and the BibleProject does sort of a dialogue in their reading of the text to help frame the conversation and accentuate the statements JESUS is making. I thought it would be fun and helpful to recreate this here this morning.
invite someone to read this with me
The version of Scripture used here is from the BibleProject.
Speaker 1:       “Don't suppose I have come to dismantle the Torah or the Prophets. I have not come to dismantle, but to fill them full” (Matthew 5:17).
Speaker 2:       Now, Jesus, I've heard that there are some people saying that you, um, are kind of loose with the Sabbath. Are you really here to honor the Torah and the Prophets? I feel like I've heard different.
Speaker 1:       “Truly, I tell you, until the sky and the land pass on, not one dot or one squiggle will pass on from the Torah, until all things have taken place” (Matthew 5:18).
Speaker 2:       Ah. So Jesus, what you're saying is you're here to honor God's will revealed in the Torah?
Speaker 1:       “Therefore, whoever undoes one of the least of these commands, and then, they teach people to do this, that person will be called least in the Kingdom of the skies. And whoever does the commands, and then, teaches his people to do them, this person will be called great in the Kingdom of the skies” (Matthew 5:19).
Speaker 2:       Oh. So Jesus, you're here to tell us how to follow God's will in the Torah. But I can go down the road to the Pharisees or the Torah teachers, and they can tell me that, too.
Speaker 1:       “Truly, I tell you, unless you're doing what is right, far surpasses that of the Scribes and Pharisees, you won't be entering into the Kingdom of the skies” (Matthew 5:20).
Thank you. Okay, so hopefully that helps us follow the logic of these four movements of thought in the statements JESUS is making. And hopefully, it will help us see the main point HE is getting at.
This morning, I am going to give you four thoughts of JESUS on the Torah (GOD’s Instruction) and the Prophets from our text this morning. Okay? So, these are
JESUS’ four thoughts on Torah:

1. Pointing Forward in Expectation.

Matthew 5:17 NASB95
17 Do not think that I came to abolish the Law or the Prophets; I did not come to abolish but to fulfill.
In our text, JESUS addresses HIS relationship to the Torah and Prophets, situating HIS teachings within the context of Israel’s covenant with GOD. The Torah, containing over 600 commands given over a thousand years before JESUS’ time, defined Israel’s identity as a KINGdom of priests tasked with blessing the nations.
Exodus 19:5–6 NASB95
5 ‘Now then, if you will indeed obey My voice and keep My covenant, then you shall be My own possession among all the peoples, for all the earth is Mine; 6 and you shall be to Me a kingdom of priests and a holy nation.’ These are the words that you shall speak to the sons of Israel.”
By the first century, under Roman occupation, the cultural context had shifted significantly from the tribal, agrarian setting of ancient Israel (agriculture, farming, or rural life) . Jewish groups, including Pharisees and Sadducees, debated how to apply these ancient commands in their contemporary setting (oppression - couldn’t observe all the laws), creating principles to bridge the cultural gap, leading to interpretive disagreements.
Pharisees: A populist, conservative group, they extended priestly commands (e.g., ritual washings) to all Israelites, aiming for strict adherence to the Torah’s original form.
Sadducees: The priestly ruling class, they collaborated with Rome and adopted a more flexible approach, prioritizing political stability over strict observance.
Scribes: Scholarly experts who copied texts, wrote commentaries, and interpreted Torah, often aligning with Pharisees or Sadducees.
So, JESUS wades into this debate - ONE Voice among many - and HE begins with a statement that is kind of two-fold in purpose: 1) it is a setup to put everyone’s mind at ease regarding HIS view of the Law and Prophets, and 2) it is anticipatory in nature of the conflicts HE will have later with these same groups of religious leaders. JESUS is ONE of many voices presenting HIS teachings as the real way to be faithful to both GOD and HIS Instruction - how to fulfill the commands of Torah.
kind of like mid-term elections
if you’re going to put yourself forward with a way of fulfilling the commands of Torah
platform to run on: of utmost importance is how you uphold the covenant commitments of Israel
The word abolish that JESUS uses is the Greek term kataluo (“to dismantle”, “to tear down”, or “abolish”). HE is anticipating accusations of being unfaithful to the covenant due to HIS unconventional interpretations, such as HIS approach to Sabbath observance, which later sparks conflicts with Pharisees and Scribes (Matthew 8–12).
It’s important to note that JESUS hasn’t given any teachings on it yet. Right? HE’s described it, HE’s given images of what HIS followers will be like in the world, but HE hasn’t explained how to apply it to every day life yet. That’s what HE’s about to do in the following verses. So, if you want to know how to apply HIS Instructions, you’ll need to come back next week; but JESUS asserts that HE fulfills the Scriptures by resolving their narrative trajectory, embodying GOD’s covenantal mission to make Israel a light to the nations through HIS teachings and life. This aligns with HIS earlier metaphors of disciples as “salt of the earth” and “light of the world”, emphasizing their role in reflecting GOD’s character and blessing the world.
Perhaps you might wonder what I mean by “narrative trajectory”? Well, listen to this quote by Dr. Tim Mackie of the BibleProject because I think this will help.
JESUS views the Scriptures as something that points forward. It has set of texts that create momentum and an expectation, a conflict that needs to be resolved in some way. And that's how JESUS reads this Bible, as a unified story that needs resolution.
So, JESUS views the Torah as something that creates momentum - it is pointing toward something. When we think about laws - particularly those in the Bible - we tend to think of them as boundaries - something to hold us back. What JESUS is going to show us is that the Torah is meant to point forward to HIS fulfillment as the Servant Isaiah spoke of (from the last message ) WHO will the embodiment of the Torah and bring true justice, true righteousness to the world. It also points forward to a time when all believers will become a royal priesthood of believers - a KINGdom filled with priests.
The apostles picks up on this theme in their writings.
Romans 10:4 NASB95
4 For Christ is the end of the law for righteousness to everyone who believes.
Galatians 3:24 NASB95
24 Therefore the Law has become our tutor to lead us to Christ, so that we may be justified by faith.
1 Peter 2:9 NASB95
9 But you are a chosen race, a royal priesthood, a holy nation, a people for God’s own possession, so that you may proclaim the excellencies of Him who has called you out of darkness into His marvelous light;
Revelation 1:6 NASB95
6 and He has made us to be a kingdom, priests to His God and Father—to Him be the glory and the dominion forever and ever. Amen.
Revelation 5:10 NASB95
10 “You have made them to be a kingdom and priests to our God; and they will reign upon the earth.”
So, JESUS did not come to abolish the Law and Prophets but to fulfill them. This clarifies that JESUS HIMSELF is the ultimate standard of righteousness. When we understand this, it can deepen our appreciation for JESUS' role in GOD's redemptive plan and set the stage for looking beyond legalistic righteousness to a relationship that transforms the heart and reflects JESUS' character.
And this leads us to the second thought on the Torah from our text this morning ...
JESUS’ four thoughts on Torah:

1. Pointing Forward in Expectation.

2. Permanence of the Word

Matthew 5:18 NASB95
18 “For truly I say to you, until heaven and earth pass away, not the smallest letter or stroke shall pass from the Law until all is accomplished.
Here JESUS emphasizes the unchanging nature or permanence of the Torah and Prophets as a key aspect of His claim to fulfill them. Look at the first part of the phrase I have emphasized here - “until heaven and earth pass away.” In John’s revelation, he described seeing a new heaven and earth:
Revelation 21:1 NASB95
1 Then I saw a new heaven and a new earth; for the first heaven and the first earth passed away, and there is no longer any sea.
This verse immediately follows the judgement when those whose names are not found in the book of life are thrown into the lake of fire. So, this is long after JESUS returns to earth for HIS bride. This description, then, affirms the Torah’s divine authority, paralleling biblical traditions that compare GOD’s Word to the most reliable elements of Creation. What is more reliable than the stable, ordered world in which we live? THE ONE WHO created it with HIS eternal Word.
In Psalm 148, all of Creation is invoked to praise the LORD. Let’s pick up in vv.5-6.
Psalm 148:5–6 NASB95
5 Let them praise the name of the Lord, For He commanded and they were created. 6 He has also established them forever and ever; He has made a decree which will not pass away.
The text portrays the skies as eternal because they were created and established by GOD’s unchanging command, which issues a decree that never passes away. This highlights the command’s stability behind Creation’s order. GOD’s command is the thing that is eternal.
The Psalmist in Psalm 102:25-27 provides a bit of contrast to this.
Psalm 102:25–27 NASB95
25 “Of old You founded the earth, And the heavens are the work of Your hands. 26 “Even they will perish, but You endure; And all of them will wear out like a garment; Like clothing You will change them and they will be changed. 27 “But You are the same, And Your years will not come to an end.
Here we see he describes the skies and earth as GOD’s handiwork that may perish or wear out like garments, subject to change through seasons, floods, or cosmic movement, yet GOD remains unchanging, with years that never end. At first glance, this might seem like conflicting messages.
However, these passages are two ways of pointing to the same ultimate truth. They illustrate a consistent biblical pattern: Creation’s regularity or constant movement (sun “rises” every morning, etc.) serves to emphasize GOD’s Eternal Nature and the enduring quality of HIS Word.
Isaiah 40:8 NASB95
8 The grass withers, the flower fades, But the word of our God stands forever.
JESUS employs this same imagery to affirm that the Torah, like GOD’s command in Creation, possesses ultimate stability, which HE fulfills - HE brings to completion - by resolving its narrative trajectory - the overarching story arc of the Hebrew Bible. Again, this language underscores the Torah’s divine authority and permanence, paralleling prophetic and psalmic traditions that compare GOD’s Word to the most reliable, eternal aspects of creation, ensuring its stability across time.
HE continues to underscore this declaration using the phrase “the smallest letter or stroke.” This is to say that not the smallest detail—referred to as a "jot and tittle" in the King James Version, or "dot and squiggle" in modern terms—will pass from the Torah until heaven and earth pass away and all things are accomplished. These minute elements, such as the distinguishing strokes in Hebrew letters (e.g., think in terms of the English language of the line differentiating a T from an L), are essential, as even subtle changes can alter meaning entirely (e.g., "taser" vs. "laser").
So, it is important to us as believers to look to CHRIST as the fulfillment of all of GOD’s promises.
2 Corinthians 1:20 NASB95
20 For as many as are the promises of God, in Him they are yes; therefore also through Him is our Amen to the glory of God through us.
In CHRIST, the promises of GOD are “yes” and “amen!” So, Beloved, value Scripture deeply and live it out authentically, so that you reflect CHRIST's righteousness in every aspect of life.
This leads us to the third point ...
JESUS’ four thoughts on Torah:

1. Pointing Forward in Expectation.

2. Permanence of the Word.

3. Preeminence of Obedience.

Matthew 5:19 NASB95
19 Whoever then annuls one of the least of these commandments, and teaches others to do the same, shall be called least in the kingdom of heaven; but whoever keeps and teaches them, he shall be called great in the kingdom of heaven.
In v.19 and v.20, which we’ll look at next, JESUS is teaching that true fulfillment of the Torah involves honoring all its commands, from the greatest to the least, as a path to greatness in the KINGdom of Heaven. He warns that undoing even the smallest command or teaching others to do so results in being least in the KINGdom, while practicing and teaching them leads to greatness.
The apostle Paul and JESUS’ brother, Jacob both restate this.
Galatians 3:10 NASB95
10 For as many as are of the works of the Law are under a curse; for it is written, “Cursed is everyone who does not abide by all things written in the book of the law, to perform them.”
James 2:10 TLV
10 For whoever keeps the whole Torah but stumbles in one point, he has become guilty of all.
JESUS’ Words in v.19 reflect the ongoing first-century Jewish debates, documented in contemporary literature and later rabbinic texts, about the hierarchy of Torah commands. So, what could perhaps come to mind when we read this verse and see the words “least” and “great” is an evaluation of the importance of a command. However, what HE is speaking to is how broad or specific a rule is. Another way to say this is there are the core commands, and then the commands on how to apply the core commands. Let’s look at an example of this in Matthew 23:23.
Matthew 23:23 NASB95
23 “Woe to you, scribes and Pharisees, hypocrites! For you tithe mint and dill and cummin, and have neglected the weightier provisions of the law: justice and mercy and faithfulness; but these are the things you should have done without neglecting the others.
JESUS critiques the Pharisees for emphasizing minor rules—such as tithing herbs —over core principles like mercy, justice, and love, which HE identifies as the greater commands. The greater commands represent broad, heart-level principles, while the lesser commands are specific applications.
JESUS’ addresses this by reassuring listeners of HIS commitment to the Torah’s authority, countering perceptions that HE might dismantle it through unconventional interpretations (e.g., Sabbath observance). By affirming every command’s importance, HE positions HIS teachings as the true embodiment of GOD’s will, transforming values and fostering a pure heart aligned with KINGdom ethics.
The language of "least" and "greatest" in the KINGdom draws from the honor-shame culture of the time, where public status signified worth. JESUS reorients this toward eternal reward: immersion in GOD’s love, which reshapes priorities and motivates faithful obedience.
Galatians 5:14 NASB95
14 For the whole Law is fulfilled in one word, in the statement, “You shall love your neighbor as yourself.”
John 14:15 NASB95
15 “If you love Me, you will keep My commandments.
This ties to the Beatitudes’ emphasis on purity of heart, where greatness arises from selfless service rather than earthly power. So, JESUS emphasizes the importance of teaching and living out even the smallest (or minor) commands. Perhaps this suggests that true greatness in the KINGdom is linked not to outward recognition but to one's faithfulness in obedience to GOD's commands in light of JESUS' teaching. This calls for humility and commitment to reflect CHRIST-centered living, enabling us to cultivate genuine inner righteousness that influences the world around us for HIS glory.
This leads into the final thought for this morning.
JESUS’ four thoughts on Torah:

1. Pointing Forward in Expectation

2. Permanence of the Word

3. Preeminence of Obedience

4. Pressing Beyond Pharisees

Matthew 5:20 NASB95
20 “For I say to you that unless your righteousness surpasses that of the scribes and Pharisees, you will not enter the kingdom of heaven.
In Matthew 5:20, JESUS declares that unless one’s righteousness—defined as doing right by GOD and others (Hebrew: *tzedekah*)—surpasses that of the scribes and Pharisees, they will not enter the KINGdom of Heaven. This statement serves as a rhetorical jab, using hyperbolic overstatements characteristic of JESUS’ teaching style, to critique the Pharisees’ focus on minor rules (e.g., tithing herbs) while neglecting core principles like mercy, justice, and love. So, where JESUS opens with a line to set the listeners at ease, HE concludes this section of text by taking a shot at the Pharisees.
JESUS’ intensity reflects intra-Jewish debates on Torah fulfillment, not broader hostility toward Judaism. HIS approach emphasizes a transformative way of life aligned with GOD’s will, visible in practices such as generosity to the poor, prayer, and fasting—actions that do right by GOD and others. Righteousness, as used in the Sermon on the Mount, involves seeking GOD’s KINGdom first, encompassing both relational harmony and obedience.
Matthew 6:33 NASB95
33 “But seek first His kingdom and His righteousness, and all these things will be added to you.
This greater righteousness fulfills the Torah and Prophets through the two greatest commandments: loving God with all one’s heart, soul, and mind (Deuteronomy 6:4–9, the Shema) and loving one’s neighbor as oneself.
Matthew 22:36–40 NASB95
36 “Teacher, which is the great commandment in the Law?” 37 And He said to him, “ ‘You shall love the Lord your God with all your heart, and with all your soul, and with all your mind.’ 38 “This is the great and foremost commandment. 39 “The second is like it, ‘You shall love your neighbor as yourself.’ 40 “On these two commandments depend the whole Law and the Prophets.”
These commands encapsulate the entire Torah, prioritizing heart-level devotion over rigid externals. The apostle Paul emphasizes that works don’t produce righteousness.
Romans 3:20–22 NASB95
20 because by the works of the Law no flesh will be justified in His sight; for through the Law comes the knowledge of sin. 21 But now apart from the Law the righteousness of God has been manifested, being witnessed by the Law and the Prophets, 22 even the righteousness of God through faith in Jesus Christ for all those who believe; for there is no distinction;
Galatians 2:16 NASB95
16 nevertheless knowing that a man is not justified by the works of the Law but through faith in Christ Jesus, even we have believed in Christ Jesus, so that we may be justified by faith in Christ and not by the works of the Law; since by the works of the Law no flesh will be justified.
JESUS' radical statement on righteousness exceeding that of the Pharisees calls us to a higher standard of inner transformation.
Ezekiel 36:26 NASB95
26 “Moreover, I will give you a new heart and put a new spirit within you; and I will remove the heart of stone from your flesh and give you a heart of flesh.
Hebrews 10:14 NASB95
14 For by one offering He has perfected for all time those who are sanctified.
2 Corinthians 3:18 NASB95
18 But we all, with unveiled face, beholding as in a mirror the glory of the Lord, are being transformed into the same image from glory to glory, just as from the Lord, the Spirit.
Inward -> out
Not outward in
Acts/works of righteousness (working out salvation) are outward expressions of the transformation of the heart. When we try to “act” before the heart is transformed, it becomes works trying to earn the FATHER’s attention and an attempt to change the heart through behavior change. That doesn’t work!
Only HOLY SPIRIT can transform a heart. Then the pure intent of the actions are based out of love and gratitude for the change inside us, not activity to earn GOD’s love.
What we will see next is that JESUS’ teachings following our text this morning—six case studies on anger, sexual ethics, manipulation, enemies, oaths, and retaliation—illustrate this heightened righteousness, addressing everyday conflicts and relationships to foster pure motives and communal transformation. Despite human failure, the vision invites growth through God’s Spirit, reshaping character, relationships, and communities toward God’s redemptive plan.
So, pj … What’s the point?

Conclusion

As we close our time in Matthew 5:17–20, remember Shackleton's desperate hunger in the Antarctic wastes—obsessed with feasts that sustained life amid despair. JESUS calls us to that same passion for righteousness (*tzedekah*), not as a burdensome ritual, but as a heart aflame with doing right by GOD and others, surpassing the Pharisees' externals through CHRIST's transformative power.
JESUS didn't come to abolish the Torah and Prophets but to propel them forward, affirming their permanence until heaven and earth pass, emphasizing obedience to every command—great and least—and pressing us toward a righteousness rooted in love for GOD and neighbor. In HIM, the Law's narrative finds fulfillment: we, as a royal priesthood, embody the SERVANT WHO brings justice to the nations, renewed by the SPIRIT into HIS Image.
Beloved, hunger and thirst for this greater righteousness, for in CHRIST, GOD's promises are "yes" and "amen". Let it reshape your heart, relationships, and communities, shining as salt and light until the new heaven and earth dawn. May we leave here committed to study, obey, and teach HIS Word, reflecting HIS perfect character in a world starving for true life. Amen.
Closing prayer & benediction
Numbers 6:24–26 NASB95
24 The Lord bless you, and keep you; 25 The Lord make His face shine on you, And be gracious to you; 26 The Lord lift up His countenance on you, And give you peace.’
Scripture records the following words in v.27:
Numbers 6:27 GW
“So whenever they use my name to bless the Israelites, I will bless them.” 
So, receive and go with the blessings of YAHWEH!
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