Reconciling Jesus and Paul on keeping the Law

For two years I have struggled and prayed to understand what seems to be an apparant contradiction in scripture.

Matthew 5:19 Therefore whoever relaxes one of the least of these commandments and teaches others to do the same will be called least in the kingdom of heaven

Galatians 3:24-25 So then, the law was our guardian until Christ came, in order that we might be justified by faith. 25 But now that faith has come, we are no longer under a guardian

In the immediate context of Matthew 5, Jesus tells his disciples that Torah wouldn’t pass until all things are fulfilled when heaven and earth pass away and so they should continue to practice every letter the law until that time. Although the heaven and earth described here are metaphorical and this passing was expected to occur in their generation when he returned (Matthew 5:18, Matthew 24:34-35, Luke 21:22), Paul doesn’t wait until this time to tell Christians they are no longer obligated to keep the law. As Paul describes, although the law hadn’t passed yet, the Christian had passed in the body of Christ. Because the Christian legally died in Christ, he was no longer required to keep the commandments (Romans 7:2-4). Was Paul “relaxing the least of these commands and teaching others to do the same?” If so, then shouldn’t Paul be called “least” in the kingdom of heaven?

Christian Jews still kept the law after Jesus’s resurrection

To make the matter more confusing, the same Paul who boldly preached that the Christian was not obligated to obey the law, himself was highly observant of the law. And not only Paul, but throughout the letters of the New Testament, the Christian Jews were zealous for keeping the Mosaic law, long after Jesus had risen.

Jesus tells Jews that they are to keep every stoke of the pen of the Mosaic law until everything is accomplished and heaven and earth disappear (Matthew 5:17-20).
Luke says it was the false, not true, witnesses who said Stephen preached against the law and said that Jesus would change the customs of Moses (Acts 6:13-14). In Stephens defense, he said nothing against the Law but claimed that Moses “received living words to pass on to us” (Acts 7:38) and “you who have received the law that was given through angels but have not obeyed it” (Acts 7:52-53).
Peter argued with God, when God asked him to break the Kosher food laws/associate with Gentiles (Acts 10:10-16, Acts 10:28).
Ananias, the one who gave Paul his sight and could hear the Lord’s voice, was described as a “devout observer of the law” (Acts 22:12).
Luke describes Paul participating in the Sabbath and reading of the Law and Prophets in the synagogues (Acts 13:14-15, 9:20, Acts 13:5). A man who was not observing the law would not have been allowed in the synagogues.
Paul still went to the Jewish temple to pray (Acts 22:17-18).
James says thousands of Jews have believed and “all of them are zealous for the law” (Acts 21:18-24). He then asked Paul to prove that he himself was devoted to the Mosaic law by making the Nazarite vow (Numbers 6) which Paul proceeds to do.
In the Jerusalem Council of Acts 15, they debated whether Gentiles should be required to keep the Mosaic law. This debate would have made no sense unless the Christian Jews believed they were required to keep the Mosaic Law themselves.
Paul goes out of his way to continue observing Jewish feasts (Acts 18:21, Acts 20:16).
He apologizes for not being obedient to the law when he reviled the High Priest (Acts 23:5).
When Paul was accused of teaching against the law (Acts 21:27-29), the Pharisees said they found no flaw with Paul’s law observance (Acts 23:9).
When Paul was attacked he defended himself saying “I was ceremonially clean when they found me” (Acts 24:17-18).
In the court of Festus, Paul testified he had done nothing wrong against the law of the Jews (Acts 25:7-8).
Paul claims he had done nothing against the Jews or their customs (Acts 28:17).
Paul says he has the right as an apostle to ask for money from those he ministers to on the basis of the Mosaic law (1 Corinthians 9:6-14).
Paul says he had blamelessly kept the law (Philippians 3:6)
Paul commands Jewish women not to speak in church in accordance with the Mosaic law (1 Corinthians 14:34)
James tells Christian Jews scattered abroad that their partiality of the rich was a violation of the command in Leviticus 19:18 (James 2:8-9). James warns them to keep the entire law and not ignore any specific provisions (James 2:10-11).
Paul permits Gentiles to eat food sacrified to idols but not Jews (1 Corinthians 8:7-9 was to Gentiles and 1 Corinthians 10:6-7,14,18-33 was written for Jews, identifying them with with their Jewish forefathers (1 Corinthians 10:1-4) and contrasting them to the pagans (1 Corinthians 10:20))
Paul teaches Gentiles not to be circumsized but that Jews should not remove the marks of circumcision (1 Corinthians 7:17-19)
Paul circumcised Timothy because they had moved to minister among Jews (Acts 16:3) whereas before when they were living among Gentiles, Timothy was not compelled to be circumcised (Galatians 2:3)

For those who don’t believe Christ has returned, these contradictory statements and behavior have produced quarreling over who is still required to keep the law, what are the consequences for disobedience, and what parts of the law are still expected of us. Were the early Christian Jews practicing the law out of ignorance, missing the same revelation Paul had, as some have suggested? Is there some other sense in which Paul believes we are not under the law that would exclude an obligation to obey it? Was Jesus telling us something that was only true at the moment he said it but shortly afterward would be replaced with more progressive revelation? Was Paul uninspired?

While some may dismiss any attempts to reconcile these contradictory statements and behavior, I believe with some investigation we can make this signficant aspect of scripture understandable. And personally, something about unresolved contradictions eats at me until I can figure it out.

Why did they practice the law after Jesus passed?

Let me start by asking a question.

Acts 15:10-11 Now then, why do you try to test God by putting on the necks of Gentiles a yoke that neither we nor our ancestors have been able to bear? 11 No! We believe it is through the grace of our Lord Jesus that we are saved, just as they are.

Peter says Christian Gentiles didn’t need to keep the law because although Jews should continue to practice it, they wouldn’t be saved by their law keeping either. So here’s the question: if they weren’t going to be saved by keeping the law, what was motivating them to practice it? Why did Jesus tell them to practice a law that wouldn’t save them?

Matthew 5:17-20 “Do not think that I have come to abolish the Law or the Prophets; I have not come to abolish them but to fulfill them. 18 For truly, I say to you, until heaven and earth pass away, not an iota, not a dot, will pass from the Law until all is accomplished. 19 Therefore whoever relaxes one of the least of these commandments and teaches others to do the same will be called least in the kingdom of heaven, but whoever does them and teaches them will be called great in the kingdom of heaven. 20 For I tell you, unless your righteousness exceeds that of the scribes and Pharisees, you will never enter the kingdom of heaven.

The law and prophets were a shadow of the things the Messiah was promised to do (Hebrews 10:1), the promises themselves, and the proof of his legitimacy. Jesus could not abolish the law without destroying the evidence he was the Messiah. And while there’s much more we could explore here, it’s the next few verses that we are concerned about.

Jesus says they were to practice the law so that that they would be called great, or inversely not be called least.

What does it mean to be called “greatest” or “least?”

But what do we imagine Jesus has in mind when he says those who practice the law exceptionally well will be called “greatest” in the kingdom of heaven? How does one become “least” by breaking the commands and teaching others to do the same?

Is it so they will be saved by their law keeping works?
Is it because their law observance will earn them more status, rewards, privileges, or reptuation in heaven?

Is it so they will be saved by their law keeping works?

While the first option may be tempting to believe, Jesus teaches salvation by believing in him:

John 3:14-16 And as Moses lifted up the serpent in the wilderness, so must the Son of Man be lifted up, 15 that whoever believes in him may have eternal life. 16 “For God so loved the world, that he gave his only Son, that whoever believes in him should not perish but have eternal life.

John 5:24 24 Truly, truly, I say to you, whoever hears my word and believes him who sent me has eternal life. He does not come into judgment, but has passed from death to life.

Peter also claims believers are not saved through law keeping (Acts 15:10-11), and Paul is adamant that salvation is not by works:

Ephesians 2:8-9 For by grace you have been saved through faith. And this is not your own doing; it is the gift of God, 9 not a result of works, so that no one may boast.

Not only that, but Jesus does not say that those who break the least of these commands and teach others to do the same will not enter the kingdom of heaven. He says they still enter, they are simply called least. The inverse of this statement is true. They could break the law and teach others to do the same and still enter the kingdom of heaven. So then this passage is not talking about salvation through law keeping. But maybe it’s talking about earning or loosing some kind of reward?

Is it because their law observance will earn them more status, rewards, privileges, or reputation in heaven?

While this explanation may at first seem to make sense, Paul seems resistant to this idea. Although Paul had more grounds than anyone to boast about his law-keeping performance he considers it garbage compared to knowing Christ and refuses to boast in his performance (Philippians 3:3-9, Galatians 6:14). He also tells us that Christ saved us by grace so that we couldn’t boast in our our earning power (Ephesians 2:8-9).

Jesus also seems to rebuke the Pharisees for obeying the law out of this same motive.

Matthew 23:5 Everything they do is done for people to see

Paul and Jesus also say that they wouldn’t be cursed for failing to keep the law (Galatians 3:13-14, John 5:24, Matthew 26:28).

Unfortunately, neither of these explanations provide a satisfactory answer. Perhaps it would help to get a better idea of what these rewards would be.

Those who serve are called great in the kingdom of heaven

If we explore how Jesus uses the terms “great” and “least” in the kingdom of heaven we find another clue.

Matthew 20:26-28 It shall not be so among you. But whoever would be great among you must be your servant, 27 and whoever would be first among you must be your slave, 28 even as the Son of Man came not to be served but to serve, and to give his life as a ransom for many.”

Mark 9:34-35 But they kept quiet because on the way they had argued about who was the greatest. 35 Sitting down, Jesus called the Twelve and said, “Anyone who wants to be first must be the very last, and the servant of all.”

Jesus said those who want to be called greatest should instead humble themselves and serve. So perhaps there is a connection between keeping the law and serving others, both cases which result in them being called “great.”

But what is it that others need that my exceptional law keeping can provide? Pehaps more love? Although love is certainly an act of service, is keeping every letter of the Mosaic law the best way to serve love to all? If so, why did it seem good to the Holy Spirit not to burden Gentiles with keeping the law (Acts 15:28)? Were they not to love? Peter describes the law as a “a yoke on the neck of the disciples that neither our fathers nor we have been able to bear” (Acts 15:10). This demands a greater purpose exists for practicing the law that cannot be fully explained in simply “being more loving.”

What service are Christian lawkeepers providing?

I did a word study on “servant” and found Paul often uses this same word in describing himself as a servant of preaching the gospel even though he is the least of all the saints (Colossians 1:24-25, Ephesians 3:7-8). In fact, in one particular verse, Paul uses all the same elements as Jesus’s statement:

1 Corinthians 9:19-20 For though I am free from all, I have made myself a servant to all, that I might win more of them. To the Jews I became as a Jew, in order to win Jews. To those under the law I became as one under the law (though not being myself under the law) that I might win those under the law.

Paul connects continuing to practice the law with serving others in order to save those “under the law” (Jews). We don’t have to read much further to see why:

1 Corinthians 10:23-24,31-33 “All things are lawful,” but not all things are helpful. “All things are lawful,” but not all things build up. 24 Let no one seek his own good, but the good of his neighbor.

31 So, whether you eat or drink, or whatever you do, do all to the glory of God. 32 Give no offense to Jews or to Greeks or to the church of God, 33 just as I try to please everyone in everything I do, not seeking my own advantage, but that of many, that they may be saved.

Paul explains that he was free to disregard the Mosaic law, all things were lawful for him, but he was foregoing that privilage and choosing to serve others by continuing to practice it regardless. Why? To avoid causing offense to unbelieving Jews. And why doesn’t he want to cause offense? So that as many as possible may be saved.

Now we can see how Paul was serving the needs of others and the gospel by obeying the law. He was making the gospel attractive and acceptable to those who might otherwise take offense at disgraceful behavior and because of it reject or slander the message he was pushing.

This seems consistent with Jesus. Afterall, Jesus has made similar statements:

Matthew 17:25-27 “What do you think, Simon?” He asked. “From whom do the kings of the earth collect customs and taxes: from their own sons, or from others?” 26 “From others,” Peter answered. “Then the sons are exempt,” Jesus declared. 27 “But so that we may not offend them, go to the sea, cast a hook, and take the first fish you catch. When you open its mouth, you will find a four-drachma coin. Take it and give it to them for My tax and yours.

The parable of the talents (Matthew 25:14-30) and Mark 4 show Jesus valued those who were effective ministers in the kingdom.

Mark 4:20 But those that were sown on the good soil are the ones who hear the word and accept it and bear fruit, thirtyfold and sixtyfold and a hundredfold.

And if Jesus and Paul had the same line of thinking, perhaps this explains what Jesus meant in our statement under question in Matthew 5. Jesus could have been saying that those who continue to practice the law so their ministry wasn’t offensive to unbelieving Jews would be called great, presumably because more Jews would be saved on account of it.

And this would also explain how the Jerusalem Council in Acts 15 was justified in only expecting law keeping of Jews. Gentiles were never fully under the law, so how would going under the law now enchance their ministry? But Jews had for a long time been under the law, so to suddenly get rid of it would have been offputting.

When in Rome do as the Romans do

Paul seems to believe this is just what Jesus was communicating:

1 Corinthians 9:1 To those outside the law I became as one outside the law (not being outside the law of God but under the law of Christ) that I might win those outside the law.

When Paul is preaching among the Gentiles, he comes “outside the law,” that is the Mosaic law, but not so far as to escape from God’s law (the law of the Gentiles, the law God places upon every man’s conscience) and he does this to be obedient to “Christ’s law,” which is Jesus’s statement in Matthew 5 that they keep the gospel unoffensive for those they are preaching to. He understood Jesus’s statement that they should practice the law in order to keep from offending Jews in their ministry and he made a new application for it following in the spirit of Jesus’s words. If they should keep the law among the Jews to keep the gospel from being offensive, then they should also go outside the law when among the Gentiles to keep the gospel from being offensive to Gentiles. In this case, Paul sees that Jesus’s point was that his ministry be unoffensive, not necessarily that they obey the law. This is why he did not circumcise Timothy when they were living among the Gentiles (Galatians 2:3), but did when they went to minister among the Jews (Acts 16:3).

So we can see how keeping the law was a form of service to help the gospel be unoffensive. But what were they earning by foregoing their freedom and instead helping to spread the gospel?

So how does providing this service make him great?

1 Corinthians 9:22-26 I have become all things to all people, that by all means I might save some. 23 I do it all for the sake of the gospel, that I may share with them in its blessings. 24 Do you not know that in a race all the runners run, but only one receives the prize? So run that you may obtain it. 25 Every athlete exercises self-control in all things. They do it to receive a perishable wreath, but we an imperishable. 26 So I do not run aimlessly; I do not box as one beating the air. 27 But I discipline my body and keep it under control, lest after preaching to others I myself should be disqualified.

In this same context, Paul expects that foregoing his freedom in order to serve and help spread the gospel would actually earn him a reward. As he says, “that I may share with them in its blessings” and that he may win “the prize.” Earlier in this letter and in others, Paul informs us of one thing he is willing to boast about:

1 Corinthians 9:1 Are not you my workmanship in the Lord?

1 Thessalonians 2:19-20 For what is our hope or joy or crown of boasting before our Lord Jesus at his coming? Is it not you? 20 For you are our glory and joy.

2 Corinthians 1:13-14 And I hope that, 14 as you have understood us in part, you will come to understand fully that you can boast of us just as we will boast of you in the day of the Lord Jesus.

Although Paul would refuse to take credit for his law-keeping, he would happy take credit for his ministry effectiveness, for the people he helped bring into the kingdom.

Now this seems like a more reasonable sense in which someone would be called great. Think of the mother who’s son chose to believe in Christ because of your example of God’s love or ministry efforts in this life. In heaven, where they are both united, wouldn’t she be eternally grateful to you? Wouldn’t she feel an everlasting appreciation for the efforts you made to bring her son there? And what about all the others your life touched? Couldn’t you imagine that God would feel proud of you for encouraging so many to enter heaven? Wouldn’t you be proud of yourself knowing you were part of the reason they got there? This seems to me what it means to be made great in the kingdom of heaven.

If this is the case, then there might be a practical reason why Jesus says that the servants are greatest in the kingdom of heaven.

The servants are most effective at expanding the kingdom of heaven

Matthew 20:25-28 But Jesus called them to him and said, “You know that the rulers of the Gentiles lord it over them, and their great ones exercise authority over them. 26 It shall not be so among you. But whoever would be great among you must be your servant, 27 and whoever would be first among you must be your slave, 28 even as the Son of Man came not to be served but to serve, and to give his life as a ransom for many.”

In other kingdoms of Jesus’s day (the Gentile kingdoms), how did they expand their empires? Through conquest, through conquering foreign lands and forcing people to become their subjects by threat of death. Their warriors and rulers were considered great for their ability to dominate and subjugate others. But in the kingdom of heaven, God doesn’t use armies to force us to believe in him. Entering into the kingdom of heaven is a choice we make of our own freewill. So how does God expand this model of kingdom? By making it as attractive as possible so that no one in their right mind would want to say no. And if winning people’s hearts over is how God’s kingdom grows, then no one does a better job of that then the humble servants. They are most effective at expanding God’s kingdom. And that’s why under this model, they are the greatest in the kingdom of heaven.

Exceptional behavior invites people into the kingdom

Controversial messages need respectable and exceptional figures to make the messages acceptable. Jesus’s ministry was a controversial message to Jews. Was Jesus truly from God? The Pharisees didn’t think so. Think of Martin Luther King Jr.’s mission to make Americans unsegregated. Such a controversial message at that time was resisted, but when people saw Martin Luther defying all black stereotypes, acting with respect, dignity, professionalism, peaceableness, kindness, with the courage of a righteousness martyr and doing so in the face of difficulties and opposition, it changed public opinion and made us realize we whites were the ones being unjust. Suddenly those who were resistant to his message found the courage to embrace it. His exceptional example of love, grace, and resilience made his message acceptable. He was “serving” the needs of black people who weren’t being accepted with dignity in American society.

The least in heaven are those who’s ministries did not produce enduring faith

1 Corinthians 3:5-15 What then is Apollos? What is Paul? Servants through whom you believed, as the Lord assigned to each. 6 I planted, Apollos watered, but God gave the growth. 7 So neither he who plants nor he who waters is anything, but only God who gives the growth. 8 He who plants and he who waters are one, and each will receive his wages according to his labor. 9 For we are God’s fellow workers. You are God’s field, God’s building.

10 According to the grace of God given to me, like a skilled master builder I laid a foundation, and someone else is building upon it. Let each one take care how he builds upon it. 11 For no one can lay a foundation other than that which is laid, which is Jesus Christ. 12 Now if anyone builds on the foundation with gold, silver, precious stones, wood, hay, straw— 13 each one’s work will become manifest, for the Day will disclose it, because it will be revealed by fire, and the fire will test what sort of work each one has done. 14 If the work that anyone has built on the foundation survives, he will receive a reward. 15 If anyone’s work is burned up, he will suffer loss, though he himself will be saved, but only as through fire.

Here we see an example of someone who suffers loss yet they themselves are saved much like Jesus saying they enter the kingdom of heaven yet are called least. It uses language of “the Day” and “fire will test the quality of each person’s work.” Peter writing just before the Neronic persecution describes that the persecutions the saints were enduring were like a fire that was testing the quality of their faith and proving them genuine (1 Peter 1:6-7). It seems those who fell away were like the straw that was burned up (1 Corinthians 3:12) while those who continued in the faith were those whose faith was built up with “gold, silver, and costly stones” (1 Corinthians 3:12) or “more precious than gold that perishes though it is tested by fire” (1 Peter 1:7). So for Paul to say that the quality of each man’s work will be tested, couldn’t this easily be interpreted as referring to the effectiveness of their ministries and the quality of faith such ministries were producing? If the fire of persecutions came, and all those you believed you had saved fell away, you are suffering loss. Perhaps the quality of your teaching or your example had not produced the love and conviction needed to endure persecution. But if those you influenced endured the persecution and stayed in the faith, you get the credit for having helped give them the conviction and love needed to endure.

What if your law keeping is as bad as the Pharisees?

Matthew 5:20 For I tell you, unless your righteousness exceeds that of the scribes and Pharisees, you will never enter the kingdom of heaven.

The word righteousness here could be interpreted as “covenant faithfulness” (Psalm 36.5–6, Psalm 88.11–12). Israel was covenented to be ministers of the oracles of God to the world (Exodus 19:5-6, Isaiah 61:6, Romans 2:18-20, Romans 3:1-2). In this case, their covenant faithfulness was how well they served as ministers of God’s word. Jesus also describes these people as those are are “teaching others.”

Jesus describes the Pharisees righteousness as prideful, self-righteousness, and a stumbling stone for accepting the faith both for themselves and others.

Matthew 23:4,11-13,34,37 They tie up heavy burdens, hard to bear, and lay them on people’s shoulders, but they themselves are not willing to move them with their finger. 11 The greatest among you shall be your servant. 12 Whoever exalts himself will be humbled, and whoever humbles himself will be exalted.

13 “But woe to you, scribes and Pharisees, hypocrites! For you shut the kingdom of heaven in people’s faces. For you neither enter yourselves nor allow those who would enter to go in.

34 Therefore I send you prophets and wise men and scribes, some of whom you will kill and crucify, and some you will flog in your synagogues and persecute from town to town,

37 “O Jerusalem, Jerusalem, the city that kills the prophets and stones those who are sent to it! How often would I have gathered your children together as a hen gathers her brood under her wings, and you were not willing!

Not only did they refuse to trust in Jesus themselves, but they actively hindered others from following him. How did the Pharisees actively hinder people from accepting the gospel?

by saying Jesus was using demons to perform his miracles (Matthew 12:24)
by hiding the evidence of his resurrection (Matthew 28:11-15)
by persecuting his followers (Matthew 23:34,37)
by trying to discredit his ministry (Matthew 12:2, Matthew 15:2)
by trying to kill him (Matthew 12:14)
by denying his miracles (Matthew 11:16-26)
by teaching righteousness according to works (Romans 10:1-4)

Jesus urges them to become like little children (Matthew 18:3-4), in the sense that they are not self-reliant and able to see that Jesus’s ministry was from God on account of the miracles he was performing (Matthew 11:16-26, John 3:2).

So when Jesus warns his audience that their righteousness must surpass that of the Pharisees, he is saying that if their service as ministers was so dissuading like the Pharisees that Jews were actively hindered from accepting the gospel, they would not enter the kingdom of heaven themselves. Such behavior would also have proven that they didn’t accept the gospel themselves.

But did Paul ever encourage Jews to break the law?

If Paul would be called least by telling Jewish Christians not to practice the law, did he earn the title “least” when in Galatians he instructed the Galatians not to be circumcised? What about when he told the Corinthians they could eat meat sacrificed to idols?

When Paul urged the Galatians to not be circumcised (Galatians 5:2-4), he was speaking specifically to Christian Gentiles. They were described as those who are not circumcized but who desired to come under the law (Galatians 4:21) and they were previously enslaved to “those that by nature are not gods” (Galatians 4:8). This is consistent with Paul elsewhere who encourages Christian Gentiles to not be circumcised and for Christian Jews to remain circumcised (1 Corinthians 7:17-19). The law was never necessary to save the Gentiles (Galatians 3:2-3), and keeping it would not improve their ministry efforts.

In the Jerusalem council, the Christian Jews ruled that Christian Gentiles did not need to keep the law, only those specific provisions that related to foreigners in Israel (Acts 15:20, Leviticus 17:8-9, Leviticus 18:6-26, Leviticus 17:13,15, Leviticus 17:10) and those that would sufficiently identify them with those who “bore God’s name” (Amos 9:12, Acts 15:17, Deut. 28:9-10). This was consistent with the words of Jesus in Matthew 5:17-20, who was speaking specifically to Jews (Matthew 15:24).

In Corinthians, Paul permits Christian Gentiles to eat food sacrificed to idols so long as it doesn’t harm a brother and so long as their consciences are pure (1 Corinthians 8:7-9). Later, speaking specifically to Christian Jews (1 Corinthians 10:1-4, 1 Corinthians 10:20), he says although a Christian Jew was lawfully free to eat food sacrified to idols in Christ (1 Corinthians 10:29), if that Jew was informed it was food sacrified to an idol he should not eat, because it would hinder his ministry effectiveness among unbelieving Jews (1 Corinthians 10:23-24,28,31-33).

Fitting the context

So when Jesus says those who continue obeying every letter of the law until it ends would be called great in the kingdom of heaven, he is saying that those who continue to practice the law in order to make the gospel appealing to unbelieving Jews would be great servants and have more reason to boast of those they saved when he returned.

This interpretation seems to explain the context well:

Matthew 5:13-16 “You are the salt of the earth, but if salt has lost its taste, how shall its saltiness be restored? It is no longer good for anything except to be thrown out and trampled under people’s feet. 14 “You are the light of the world. A city set on a hill cannot be hidden. 15 Nor do people light a lamp and put it under a basket, but on a stand, and it gives light to all in the house. 16 In the same way, let your light shine before others, so that they may see your good works and give glory to your Father who is in heaven.

Jesus wants his people to live such exemplary lives his message will be accepted. The saltiness refers to their reputation as good people. For instance, as of 2021, for serveral years now, Venezuelans have been fleeing the total chaos and dictatorship in their home country and are trying to start new lives among neighboring countries. At first, the surrounding countries greeted them with open arms, but then the dictator of Venezuela, who wanted to reduce the exodus, sent rotten Venezuelans to pose as immigrants in those countries and stir up trouble and commit crimes. When the people of those countries saw a few Venezuelans commiting crimes they were enraged at all Venezuelans and began protests to remove all Venezuelans from their countries. At first, the fleeing Venezuelans had saltiness and were well received, but when they lost their saltiness, that is their reputations for being great business leaders and capable workers, and instead because known as criminals, what could they do to restore their reputation? The damage had been done.

Jesus wanted people to see how Christians’ works were exceptional and make the gospel appealing to outsiders. When outsiders would see their light (good works), they would give glory to God. Paul agrees with this:

1 Thessalonians 4:11-12 and to make it your ambition to lead a quiet life: You should mind your own business and work with your hands, just as we told you, 12 so that your daily life may win the respect of outsiders and so that you will not be dependent on anybody.

Summary

Here’s how I understand Matthew 5:19-20:

If your freedom causes the Jews to stumble in accepting the gospel you will be called least in the kingdom of heaven. But if by keeping the law, you make the gospel less offensive to Jews you will be called great. If your service as a minister is so dissuading like the Pharisees that Jews are actively prevented from accepting the gospel, you will not enter the kingdom of heaven yourselves. (Jon Paul’s interpretation)

If this is how we should interpret Jesus, then Paul and Jesus do not contradict each other.

Jesus, Paul, and Peter all preached salvation by faith, not works (John 3:14-16, Ephesians 2:8-9, Acts 15:11). Although, Jesus taught that it was important for your righteousness to surpass that of the Pharisees in order to enter heaven, he later describes their righteousness as prideful, self-reliant and a stumbling block for accepting the gospel both for themselves and for others. Humility, giving up on self-reliance and trusting Christ and seeing the credibility of Jesus’s ministry that was so obvious a child could see it, would allow them to enter. This does not contradict salvation by faith, it is saying that if your understanding of the law makes you proud and self-reliant so that you refuse the gospel, you don’t really have the faith needed to enter the kingdom of heaven.
Paul and Jesus both taught that both Christian Jews and Gentiles will not be cursed by their failure to keep the law (Galatians 3:13-14, John 5:24).
Jesus did not preach the law had passed yet and Paul also did not preach that the law had passed. According to Paul, Christian Jews and Gentiles were freed from the obligations of the law, not because the law had passed, but because when Christ, who was our legal representative, was put to death, we legally died with him, and it ended our obligations to obey the law in the same way that a widow is free to remarry after her husband dies and is not called an adulteress (Galatians 2:19-20, Romans 7:2-4, Galatians 3:24-25).
While Christian Jews were free from the law, Jesus instructed them to continue practicing it so the gospel wouldn’t be hindered from growing among the doubtful and unbelieving Jews. Even in Matthew 17:24-27, Jesus tells his disciples that they are not obligated to pay the temple tax but recommends they do so regardless so that they wouldn’t cause offense. Paul likewise instructed his followers to live godly lives (Philippians 1:10), win the respect of outsiders (1 Thessalonians 4:11-12), not to use their freedom to hinder the spread of the gospel (1 Corinthians 10:23-24,33), and not to offend anyone so as many as possible could be saved (1 Corinthians 10:32-33). He encouraged Christian Jews to keep specific provisions of the law to help win the skeptical Jews (1 Corinthians 14:34,37), and he himself lived a life of exceptional law keeping (Philippians 3:6) by the power of the Spirit.

So how do Paul and Jesus contradict each other? Both agree that the motivation for practicing law should not be for earning salvation, for fear of a curse, or for feeling like they were obligated to. They agreed they were to practice the law, only to help the ministry of the gospel be acceptable to lost Jews and even then only for a specific time period, “until all is fulfilled.”

Thus, Paul and Jesus are reconciled. We can trust Paul’s bold statements about the law at face value and can reconcile it with Jesus when we correlate Matthew 5 with other statements from Jesus.

Today we don’t have to keep the Mosaic law

As that generaton was coming to a close, the book of Hebrews was written to encourage the believers to stop practicing the law because it was about to pass and the temple was about to be destroyed (Hebrews 4:1, Hebrews 8:13, Hebrews 13:11-14, Hebrews 10:26-31,37-38, Matthew 24:2-3,34-35). When it finally did pass, the Levitical ancestoral records were destroyed making an authentic practice of the Mosaic law impossible. Today, Christian Jews are not encouraged to keep the law even as a ministry tool, because it truly has passed.

Instead, we are fully under the New Covenant and our example is love, faith, truth, and grace.

Hebrews 8:10-12 I will put my laws in their minds and write them on their hearts. I will be their God, and they will be my people. 11 No longer will they teach their neighbor, or say to one another, ‘Know the Lord,’ because they will all know me, from the least of them to the greatest. 12 For I will forgive their wickedness and will remember their sins no more.”