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Fulfilling and Failing at the Law (Matthew 5:17-20)

First Baptist Church https://fbcbartow.org

“Fulfilling and Failing at the Law”

(Matthew 5:17-20)

Series: God’s Fulfilled Promise [on screen]

Rev. Matthew C. McCraw, EdD

First Baptist Church, Bartow, Florida

September 23, 2018

Introductory Comments:

Illustration: One of my favorite movies is the movie, Braveheart. In the movie the Scottish people are under English oppression from the domineering king, Edward the Long-shanks. A Scottish commoner named William Wallace starts an uprising and the people begin to see victory. Wallace becomes bold and says that the resistance will now invade England and face Long-shanks in his own land. The pessimistic Scottish nobles tell Wallace that it is impossible to invade England. Wallace, asks “Why,” and he challenges the nobles to support him. You see, it seemed impossible to them because of the seemingly insurmountable obstacles in front of them. 

In the Christian life, we are called to follow the law of God. In fact, in the book of Matthew, Jesus has been laying out what a follower of God looks like. Some of us may see and hear what God wants us to do; how He wants us to live, and think, “Well, that’s impossible!”

We’re going to see in today’s passage that Jesus doesn’t relax the standard for God’s law at all. He clarifies that we are called to ultimate righteous living. 

How can we possibly accomplish this?

Well, let’s look at the passage together and see. 

Read the Passage

(Read Matthew 5:17-20)

17 “Don’t think that I came to abolish the Law or the Prophets. I did not come to abolish but to fulfill. 18 For truly I tell you, until heaven and earth pass away, not the smallest letter or one stroke of a letter will pass away from the law until all things are accomplished. 19 Therefore, whoever breaks one of the least of these commands and teaches others to do the same will be called least in the kingdom of heaven. But whoever does and teaches these commands will be called great in the kingdom of heaven. 20 For I tell you, unless your righteousness surpasses that of the scribes and Pharisees, you will never get into the kingdom of heaven.

Let’s pray together.


Here we see that Jesus is continuing to deliver the most famous sermon in history: the sermon on the mountainside. 

He has told us that we are blessed if we live as God has called us to live; He’s told us to live as influencers in the world, as salt and light; and now He speaks to us regarding the law of God. 


Let us discover now three truths related to the law of God from this passage. 

First, . . .

I. Jesus fulfills the law (vv. 17-18) [on screen]

Remember, that most of the content that Jesus is teaching His listeners is unusual to them. It’s countercultural. 

So, many of Jesus’ listeners may have thought that Jesus was against the official Jewish teaching of the day, or against the teaching of the law and prophets. 

By the way, the “law and the prophets” referred to the historic teachings of the Old Testament, which at that time was the only Bible that the Jewish people had. 

Jesus is saying, “Don’t be misinformed! I didn’t come to do away with the Bible!”

He did not come to work around the law, but to perfectly obey and fulfill it.

This would have captured the attention of the people. To know that He is not doing something different from what God had been doing since He called Abraham and said “I will make a great nation out of you,” and when He delivered the law to Moses, and when He spoke through the prophets. 

Jesus says, “I am going to fulfill all that was delivered to you through Abraham, Moses, and the prophets.”

Jesus said that every little detail matters in the law. 

The Christian Standard Bible says in verse 18 “the smallest letter” and just “one stroke” matters. 

The original language would have spoken to some distinguishing marks of the written Hebrew language. 

Jesus said every “jot” and “tittle” matter.  A “jot” referred to the smallest Hebrew letter, while a “tittle” referred to a stroke that would distinguish two different letters. 

Basically, it’s like saying, “every dot on an i and the stroke that distinguishes a capital P from a capital R matter when it comes to the law.” Every detail matters!

Jesus is wanting to make sure we know that the Old Testament teachings matter. They mattered during the time of Moses, they mattered during the time of Jesus, and they matter today. 

Second Timothy 3:16 tells us,

16 All Scripture is inspired by God and is profitable for teaching, for rebuking, for correcting, for training in righteousness, [on screen]

All Scripture is beneficial for us!

The law and the prophets are binding, they are authoritative, and they are the Word of God. 

Jesus would fulfill the law and the prophets perfectly and fully, and He’s the only one that could; and He did!

He not only obeyed them, He fulfilled them. He brought clarity to them. He was the cherry on top; He was the icing on the cake; He made the law and the prophets what they were meant to be. 

The law and the prophets matter, and Jesus fulfilled them. 

Next, . . .

II. Greatness follows obedience to the law (v. 19) [on screen]

Look at verse 19 again. 

(Read Matthew 5:19)

19 Therefore, whoever breaks one of the least of these commands and teaches others to do the same will be called least in the kingdom of heaven. But whoever does and teaches these commands will be called great in the kingdom of heaven.

Jesus makes it very clear, if we don’t obey the law we are least in the kingdom of heaven and if we do obey the law we are great in the kingdom of heaven. Well, that’s pretty straightforward. 

Yet, it’s also confusing. Why? Because all of us will fail at some point in our lives on at least one part of the commands of God!

So, if we do, according to this verse, we are called least in the kingdom of heaven. That is not a good situation!

Sometimes we may be tempted to think that some of the sins we commit are not that big of a deal. 

Jesus will speak of that in next week’s passage. 

However, in this passage Jesus says, “whoever breaks one of the least of these.”

Every little command of God matters. Don’t minimize your sin, because it’s not minimal to a holy God. 


Jesus also says that if we do obey the commands of God we will be called great. 

I want some of that! I want to be great!

The question is, “How do we obey the law, so we can be great in the kingdom of heaven?”

Jesus answers the question for us in verse 20. 

Let’s look at verse 20 again. 

20 For I tell you, unless your righteousness surpasses that of the scribes and Pharisees, you will never get into the kingdom of heaven.

That takes us to our last point:

III. We will fail at the law (v. 20) [on screen]

Some of you are thinking, “What a let down! Pastor Matt! You are a terrible motivational speaker!”

Here’s the deal: God’s standard of being great in the kingdom of heaven is obedience to the law, even in the little things. We’re all going to mess that up. 

Romans 3:23 says, “For all have sinned and fall short of the glory of God.” [on screen]

I don’t have to convince you all of this. You know yourselves. You know you’re not perfect. I surely know that I’m not perfect. 

In fact, the standard that Jesus gives us for righteousness would have floored His listeners at the time. 

He said that we must be more righteous than the scribes and Pharisees. 

The scribes and Pharisees were the pinnacle of righteousness in that day. 

The people would die to be as righteous as the scribes and Pharisees, and Jesus says that you must be more righteous than then are. 

If that’s the case, there’s no hope for us to be able to be righteous enough. 

Are you catching on?


On our own, we are unable to fulfill the law. 

Did you catch that? On our own, we are unable to fulfill the law. 


That’s why we need Jesus. 

We need the righteousness of Jesus to help us obey the law!

The law and the prophets show us God’s way, and in part, they show us that we cannot measure up to God’s standard, which shows us evermore that we need God’s grace in our lives. 

We need Jesus’ forgiveness. 

You see, Jesus did fulfill the law. He was perfectly obedient, even in the little things. His righteousness did exceed that of the Pharisees.

So, Jesus will pay the penalty for our unrighteousness, and we will receive the blessing of being called great in the kingdom of heaven because of His righteousness.  

First Peter 3:18 tells us, “For Christ also suffered for sins once for all, the righteous for the unrighteous, that he might bring you to God.” [on screen]

In order for us to live righteously, and be called great in the kingdom of heaven, something has to change in us. 

Concluding Thoughts:

Jesus fulfills the law, we fail at the law. 

Jesus is righteous, we are unrighteous. 

We need the help and healing of Jesus, and praise God that He offers it. 

John tells us in 1 John 1:9, “If we confess our sins, he is faithful and righteous to forgive us our sins and to cleanse us from all unrighteousness.” [on screen]

He can change our unrighteousness. He can give us new hearts which can then be faithful to God’s ways. We can live as God has called us to live. 

Here’s our bottom line this week:

Bottom Line: Jesus fulfilled the law, so we could faithfully follow the Father.  [on screen]


Without Jesus, we will fail when it comes to living for God. With Jesus, we have new lives and new hearts, that can be devoted to Jesus. 

If you’ve not done so already, give your heart to Jesus today. 

If you’re already a follower of Jesus, commit to live the righteous life that you’ve been set free to live. 

Let’s challenge ourselves in the following ways this week:

Weekly Challenge: [on screen]

  1. Identify one law of God that you have failed to obey.  [on screen]

Ask God to forgive you. 

Perhaps you haven’t forgiven someone. Perhaps you haven’t loved the way that you should. Perhaps you’ve had a prideful heart. 

Whatever it is, ask God to forgive you and then make it right.

Thank God for His grace and for giving you new righteousness. 

Live for Him!

  1. Identify one law of God that you will fulfill this week.  [on screen]

Ask God to guide you with His Holy Spirit. 

You are now set free to live for God with the righteousness of Jesus!

Commit to live a new life in Jesus and fulfill the law of God. 


The call to righteousness is a serious requirement from God to humanity. God does not mess around with sin. 

The fact that we know the depth of our own sin and our own unrighteousness should drive us straight to the cross of Jesus. 

We need to be changed! We need to be made new! We need to live new lives of righteousness, devoted to God!

Some of us may be tempted to think that we are good enough; that we are righteous enough. Don’t be so foolish! Your natural human righteousness does not exceed that of the Pharisees and it certainly doesn’t meet God’s requirement. 

Ephesians 2:8-9 tells us “For you are saved by grace through faith, and this is not from yourselves; it is God’s gift—not from works, so that no one can boast.” [on screen

(Gospel Presentation)

(Closing Prayer)

Invitation Song – Softly and Tenderly


Please be seated, church. 

If you have any sort of spiritual decision that you would like to make, you can contact me or Pastor Richard and we would be glad to talk to you anytime.

I hope to see you back here tonight at 5:30 for our series An Expedition in the Bible. We are now in the New Testament. I think you’ll enjoy being here. 

Before we dismiss I’d like for us to hear a message from a member of our church family, then follow that with a time of prayer. I’m going to ask Marvin Pittman, one of our deacons, to come share with us and lead us in prayer. After that, we’ll dismiss with the doxology. 

(Marvin comments and prays)

(Sing Doxology)

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