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King James Version
Whosoever therefore shall break one of these least commandments, and shall teach men so, he shall be called the least in the kingdom of heaven: but whosoever shall do and teach them, the same shall be called great in the kingdom of heaven.
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KJV (with Strong's)
Whosoever G3739 G1437 therefore G3767 shall break G3089 one G3391 of these G5130 least G1646 commandments G1785, and G2532 shall teach G1321 men G444 so G3779, he shall be called G2564 the least G1646 in G1722 the kingdom G932 of heaven G3772: but G1161 whosoever G3739 G302 shall do G4160 and G2532 teach G1321 them, the same G3778 shall be called G2564 great G3173 in G1722 the kingdom G932 of heaven G3772.
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Complete Jewish Bible
So whoever disobeys the least of these mitzvot and teaches others to do so will be called the least in the Kingdom of Heaven. But whoever obeys them and so teaches will be called great in the Kingdom of Heaven.
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Berean Standard Bible
So then, whoever breaks one of the least of these commandments and teaches others to do likewise will be called least in the kingdom of heaven; but whoever practices and teaches them will be called great in the kingdom of heaven.
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American Standard Version
Whosoever therefore shall break one of these least commandments, and shall teach men so, shall be called least in the kingdom of heaven: but whosoever shall do and teach them, he shall be called great in the kingdom of heaven.
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World English Bible Messianic
Whoever, therefore, shall break one of these least commandments, and teach others to do so, shall be called least in the Kingdom of Heaven; but whoever shall do and teach them shall be called great in the Kingdom of Heaven.
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Geneva Bible (1599)
Whosoeuer therefore shall breake one of these least commandements, and teach men so, he shall be called the least in the kingdome of heauen: but whosoeuer shall obserue and teach them, the same shall be called great in the kingdome of heauen.
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Young's Literal Translation
`Whoever therefore may loose one of these commands--the least--and may teach men so, least he shall be called in the reign of the heavens, but whoever may do and may teach them , he shall be called great in the reign of the heavens.
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In the KJVVerse 23,254 of 31,102

Study This Verse

SUMMARY

Matthew 5:19 encapsulates Jesus' profound affirmation of the enduring authority and comprehensive nature of God's Law, challenging any notion of its trivialization. It delineates a clear contrast between those who disregard even the seemingly "least" of God's commands and teach others to do likewise, and those who diligently obey and faithfully teach them. Jesus declares that one's posture toward God's revealed will—both in personal conduct and public instruction—directly impacts their standing, honor, or influence within the present and future reality of the kingdom of heaven.

CONTEXT

  • Literary Context: This verse is a pivotal statement within Jesus' Sermon on the Mount, specifically following His declaration in Matthew 5:17-18 that He did not come to abolish the Law or the Prophets, but to fulfill them. It serves as a direct elaboration on the implications of His mission concerning the Mosaic Law. Jesus is establishing a new standard of righteousness, one that surpasses the external, often superficial, observance of the scribes and Pharisees, as further emphasized in Matthew 5:20. The immediate context underscores the continuity and divine authority of God's commands, setting the stage for Jesus' subsequent re-interpretations and deeper applications of the Law throughout the remainder of Matthew 5.
  • Historical & Cultural Context: In first-century Judaism, the Torah (Law) was central to identity and piety. Rabbinic tradition often categorized commandments as "heavy" (important) or "light" (less important), though all were considered divine. Jesus' statement challenges any human-made hierarchy that might lead to the neglect of certain commands. The "kingdom of heaven" was a prevalent concept, signifying God's sovereign rule, which Jews anticipated would be fully established on earth. While many expected a political kingdom, Jesus consistently redefines it as a spiritual reality that has both present and future dimensions, entered through repentance and faith, and characterized by obedience to God's will, as taught in Matthew 3:2. His teaching here would have been revolutionary, asserting His own authority as the ultimate interpreter of the Law, even over established rabbinic traditions.
  • Key Themes: Matthew 5:19 contributes significantly to several key themes in the Gospel of Matthew and the broader biblical narrative. Firstly, it reinforces the enduring authority and integrity of God's Law, demonstrating that every part of God's revealed will, no matter how seemingly insignificant, carries divine weight. Secondly, it highlights the theme of true righteousness, emphasizing that genuine discipleship involves not just hearing but also actively "doing" God's commands, as Jesus later stresses in Matthew 7:24-27. Thirdly, the verse underscores the responsibility of teaching, particularly for those who would lead others in the kingdom. It warns against undermining God's truth and commends those who faithfully transmit it. Finally, it speaks to the nature of the kingdom of heaven, clarifying that while salvation is by grace, there are varying degrees of honor or standing within the kingdom, based on faithfulness and obedience, a concept echoed in passages like Luke 19:11-27.

EXPOSITION AND ANALYSIS

Key Word Analysis

  • break (Greek, lýō', G3089): Meaning "to loosen" (literally or figuratively), "destroy," "dissolve," or "put off." In this context, it signifies to annul, disregard, or treat as invalid. Jesus uses it to convey the profound seriousness of undermining or failing to uphold God's commandments, implying a deliberate act of setting aside or making void the divine standard.
  • least (Greek, eláchistos', G1646): A superlative form meaning "least" in size, amount, or dignity; very little or smallest. This word is used twice in the verse. First, it refers to the "least commandments," emphasizing that even the seemingly minor or less significant commands of God are not to be dismissed. Second, it refers to being "called the least" in the kingdom, indicating a position of diminished honor or influence, not exclusion from the kingdom itself.
  • teach (Greek, didáskō', G1321): Meaning "to teach" in a broad application. This highlights the dual responsibility Jesus places on His followers: not only to obey God's commands themselves ("do") but also to instruct others in them. The verse contrasts teaching a disregard for the Law with teaching its faithful observance, underscoring the immense impact and accountability associated with spiritual instruction.

Verse Breakdown

  • "Whosoever therefore shall break one of these least commandments, and shall teach men so,": This opening clause establishes the negative scenario. "Whosoever" indicates a universal principle applicable to anyone. "Therefore" links back to Jesus' affirmation of the Law in Matthew 5:17-18. To "break" a commandment implies not merely a failure to obey, but an active disregard or a deliberate act of undermining its authority. The phrase "one of these least commandments" emphasizes that no part of God's revealed will, however minor it may seem to human perception, is to be treated lightly. The addition "and shall teach men so" highlights the severe consequence of not only personal disobedience but also influencing others to adopt a similar dismissive attitude toward God's standards.
  • "he shall be called the least in the kingdom of heaven:": This clause presents the consequence for the one who breaks and teaches against the commandments. To be "called the least" does not imply exclusion from the kingdom but rather a diminished status, honor, or influence within it. The "kingdom of heaven" refers to God's sovereign rule, which is both a present reality (entered by faith and obedience) and a future consummation. This consequence speaks to a loss of reward or recognition, rather than a loss of salvation, which is by grace through faith.
  • "but whosoever shall do and teach [them],": This clause introduces the contrasting, positive scenario, marked by the adversative "but." It describes the faithful disciple. "Whosoever" again emphasizes the universal applicability. The phrase "shall do and teach [them]" sets forth the ideal of comprehensive obedience and faithful instruction. It's not enough to merely know the commands; one must embody them in action ("do") and then accurately transmit them to others ("teach"). This demonstrates a deep reverence for God's authority and a commitment to His truth.
  • "the same shall be called great in the kingdom of heaven.": This final clause presents the consequence for the obedient and faithful teacher. Just as the "least" implies diminished honor, being "called great" signifies a position of high honor, influence, and reward within the kingdom of heaven. This greatness is not a matter of human pride but a divine recognition of faithful stewardship and diligent obedience to God's will, both personally and in teaching others. It serves as an encouragement for disciples to pursue a life of integrity and faithful service.

Literary Devices

Matthew 5:19 is rich in literary devices that enhance its message. The most prominent is Antithesis, where two opposing ideas are placed in juxtaposition to create a strong contrast. Here, the "one who breaks and teaches so" is contrasted with "the one who does and teaches," leading to diametrically opposed outcomes: "called the least" versus "called great" in the kingdom of heaven. This stark contrast powerfully underscores the critical importance of obedience and faithful teaching. Parallelism is also evident, as the two halves of the verse mirror each other in structure, reinforcing the comparative nature of the teaching. The phrase "kingdom of heaven" functions as a central Metaphor, representing God's active rule and reign, which is both a present spiritual reality and a future eschatological hope. This metaphorical language grounds the ethical instruction in a theological framework of divine sovereignty and ultimate accountability.

THEOLOGICAL AND THEMATIC CONNECTIONS

Matthew 5:19 stands as a testament to the enduring significance of God's moral law within the new covenant, not as a means of salvation, but as the standard for kingdom living and a reflection of God's character. It clarifies that Jesus' fulfillment of the Law does not abrogate its ethical demands but rather intensifies them, calling for an obedience rooted in the heart. The verse highlights that true discipleship involves both personal adherence to God's will and faithful stewardship of His truth in teaching others. This integrity of life and doctrine is not merely a suggestion but a foundational principle for those who claim citizenship in God's kingdom, impacting their honor and influence within that divine realm. It underscores that while grace alone saves, our works demonstrate the reality of our faith and contribute to our eternal reward.

REFLECTION AND APPLICATION

Matthew 5:19 calls believers to a profound and holistic commitment to God's Word. It challenges us to examine our attitudes toward all of Scripture, recognizing that even the "least" of God's commands are expressions of His divine will and wisdom. This verse compels us to move beyond superficial obedience, urging us to diligently "do" what God commands, allowing His truth to shape every aspect of our lives—our thoughts, words, and actions. Furthermore, it places a weighty responsibility on anyone who teaches or influences others, whether formally from a pulpit or informally in daily conversations. We are called to handle God's Word with utmost integrity, never diminishing its authority or relevance for the sake of convenience, popularity, or personal preference. Our faithfulness in both obedience and teaching reflects our reverence for God and has eternal implications for our standing and usefulness in His kingdom, reminding us that our lives are a testimony to the truth we proclaim.

Questions for Reflection

  • In what areas of my life might I be tempted to dismiss certain commandments as "least" or less important?
  • How does my personal obedience (or lack thereof) align with what I teach or advocate to others about God's Word?
  • What does it mean for me to be "great" in the kingdom of heaven, and how does this motivate my daily choices?

FAQ

Does "least in the kingdom of heaven" mean one is not saved?

Answer: No, the phrase "least in the kingdom of heaven" does not imply a loss of salvation. The context of the Sermon on the Mount, and indeed the entire New Testament, clearly teaches that salvation is a gift of God's grace, received through faith in Jesus Christ, not by perfect obedience to the Law (e.g., Ephesians 2:8-9). Instead, Jesus is speaking about varying degrees of honor, reward, or influence within the kingdom. Those who disregard God's commands and lead others astray will have a diminished standing, while those who faithfully obey and teach will be highly esteemed. It's a matter of spiritual stature and commendation, not eternal destiny. The very fact that they are "in the kingdom" indicates their salvation.

What does Jesus mean by "least commandments"?

Answer: In Jewish tradition, commandments were sometimes categorized as "heavy" or "light" based on their perceived importance or difficulty. However, Jesus' statement here challenges any human attempt to diminish the importance of any part of God's Law. By "least commandments," Jesus emphasizes that all of God's commands, down to their seemingly most minor details, carry divine authority and are significant in His eyes. He is not endorsing a hierarchy of importance but rather condemning the attitude that would allow one to disregard any part of God's revealed will. This aligns with the principle that God's Law is a unified whole, as seen in James 2:10.

CHRIST-CENTERED FULFILLMENT

Matthew 5:19 finds its ultimate fulfillment in Jesus Christ, who perfectly embodies the "great" one in the kingdom of heaven. Unlike those who would break or diminish the commandments, Jesus Himself lived a life of flawless obedience, fulfilling every jot and tittle of the Law, as declared in Matthew 5:17. He is the only one who truly "did" God's will without blemish, serving as our perfect example and the righteous standard by which all humanity falls short (Hebrews 4:15). Furthermore, Jesus perfectly "taught" the commandments, not only explaining their true spiritual depth and intent, as seen throughout the Sermon on the Mount, but also commissioning His disciples to teach "all things whatsoever I have commanded you" (Matthew 28:19-20). Our ability to "do and teach" these commandments is not by our own strength but by the power of the Holy Spirit, whom Christ sends to indwell and empower us (John 14:26). Thus, our standing as "great" in the kingdom is ultimately derived from our union with Christ and His perfect obedience imputed to us, enabling us to live out and proclaim His righteous standards as a response to His grace.

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Commentary on Matthew 5 verses 17–20

I. II. Main points1. 2. Sub-points

Those to whom Christ preached, and for whose use he gave these instructions to his disciples, were such as in their religion had an eye, 1. To the scriptures of the Old Testament as their rule, and therein Christ here shows them they were in the right: 2. To the scribes and the Pharisees as their example, and therein Christ here shows them they were in the wrong; for,

I. The rule which Christ came to establish exactly agreed with the scriptures of the Old Testament, here called the law and the prophets. The prophets were commentators upon the law, and both together made up that rule of faith and practice which Christ found upon the throne in the Jewish church, and here he keeps it on the throne.

1.He protests against the thought of cancelling and weakening the Old Testament; Think not that I am come to destroy the law and the prophets. (1.) "Let not the pious Jews, who have an affection for the law and the prophets, fear that I come to destroy them." Let them be not prejudiced against Christ and his doctrine, from a jealousy that this kingdom he came to set up, would derogate from the honour of the scriptures, which they had embraced as coming from God, and of which they had experienced the power and purity; no, let them be satisfied that Christ has no ill design upon the law and the prophets. "Let not the profane Jews, who have a disaffection to the law and the prophets, and are weary of that yoke, hope that I am come to destroy them." Let not carnal libertines imagine that the Messiah is come to discharge them from the obligation of divine precepts and yet to secure to them divine promises, to make the happy and yet to give them leave to live as they list. Christ commands nothing now which was forbidden either by the law of nature or the moral law, nor forbids any thing which those laws had enjoined; it is a great mistake to think he does, and he here takes care to rectify the mistake; I am not come to destroy. The Saviour of souls is the destroyer of nothing but the works of the devil, of nothing that comes from God, much less of those excellent dictates which we have from Moses and the prophets. No, he came to fulfil them. That is, [1.] To obey the commands of the law, for he was made under the law, Gal 4:4. He in all respects yielded obedience to the law, honoured his parents, sanctified the sabbath, prayed, gave alms, and did that which never any one else did, obeyed perfectly, and never broke the law in any thing. [2.] To make good the promises of the law, and the predictions of the prophets, which did all bear witness to him. The covenant of grace is, for substance, the same now that it was then, and Christ the Mediator of it. [3.] To answer the types of the law; thus (as bishop Tillotson expresses it), he did not make void, but make good, the ceremonial law, and manifested himself to be the Substance of all those shadows. [4.] To fill up the defects of it, and so to complete and perfect it. Thus the word plērōsai properly signifies. If we consider the law as a vessel that had some water in it before, he did not come to pour out the water, but to fill the vessel up to the brim; or, as a picture that is first rough-drawn, displays some outlines only of the piece intended, which are afterwards filled up; so Christ made an improvement of the law and the prophets by his additions and explications. [5.] To carry on the same design; the Christian institutes are so far from thwarting and contradicting that which was the main design of the Jewish religion, that they promote it to the highest degree. The gospel is the time of reformation (Heb 9:10), not the repeal of the law, but the amendment of it, and, consequently, its establishment.

2.He asserts the perpetuity of it; that not only he designed not the abrogation of it, but that it never should be abrogated (Mat 5:18); "Verily I say unto you, I, the Amen, the faithful Witness, solemnly declare it, that till heaven and earth pass, when time shall be no more, and the unchangeable state of recompences shall supersede all laws, one jot, or one tittle, the least and most minute circumstance, shall in no wise pass from the law till all be fulfilled;" for what is it that God is doing in all the operations both of providence and grace, but fulfilling the scripture? Heaven and earth shall come together, and all the fulness thereof be wrapped up in ruin and confusion, rather than any word of God shall fall to the ground, or be in vain. The word of the Lord endures for ever, both that of the law, and that of the gospel. Observe, The care of God concerning his law extends itself even to those things that seem to be of least account in it, the iotas and the tittles; for whatever belongs to God, and bears his stamp, be it ever so little, shall be preserved. The laws of men are conscious to themselves of so much imperfection, that they allow it for a maxim, Apices juris non sunt jura - The extreme points of the law are not the law, but God will stand by and maintain every iota and every tittle of his law.

3.He gives it in charge to his disciples, carefully to preserve the law, and shows them the danger of the neglect and contempt of it (Mat 5:19); Whosoever therefore shall break one of the least commandments of the law of Moses, much more any of the greater, as the Pharisees did, who neglected the weightier matters of the law, and shall teach men so as they did, who made void the commandment of God with their traditions (Mat 15:3), he shall be called the least in the kingdom of heaven. Though the Pharisees be cried up for such teachers as should be, they shall not be employed as teachers in Christ's kingdom; but whosoever shall do and teach them, as Christ's disciples would, and thereby prove themselves better friends to the Old Testament than the Pharisees were, they, though despised by men, shall be called great in the kingdom of heaven. Note, (1.) Among the commands of God there are some less than others; none absolutely little, but comparatively so. The Jews reckon the least of the commandments of the law to be that of the bird's nest (Deu 22:6, Deu 22:7); yet even that had a significance and an intention very great and considerable. (2.) It is a dangerous thing, in doctrine or practice, to disannul the least of God's commands; to break them, that is, to go about either to contract the extent, or weaken the obligation of them; whoever does so, will find it is at his peril. Thus to vacate any of the ten commandments, is too bold a stroke for the jealous God to pass by. it is something more than transgressing the law, it is making void the law, Psa 119:126. (3.) That the further such corruptions as they spread, the worse they are. It is impudence enough to break the command, but is a greater degree of it to teach men so. This plainly refers to those who at this time sat in Moses' seat, and by their comments corrupted and perverted the text. Opinions that tend to the destruction of serious godliness and the vitals of religion, by corrupt glosses on the scripture, are bad when they are held, but worse when they are propagated and taught, as the word of God. He that does so, shall be called least in the kingdom of heaven, in the kingdom of glory; he shall never come thither, but be eternally excluded; or, rather, in the kingdom of the gospel-church. He is so far from deserving the dignity of a teacher in it, that he shall not so much as be accounted a member of it. The prophet that teaches these lies shall be the tail in that kingdom (Isa 9:15); when truth shall appear in its own evidence, such corrupt teachers, though cried up as the Pharisees, shall be of no account with the wise and good. Nothing makes ministers more contemptible and base than corrupting the law, Mal 2:8, Mal 2:11. Those who extenuate and encourage sin, and discountenance and put contempt upon strictness in religion and serious devotion, are the dregs of the church. But, on the other hand, Those are truly honourable, and of great account in the church of Christ, who lay out themselves by their life and doctrine to promote the purity and strictness of practical religion; who both do and teach that which is good; for those who do not as they teach, pull down with one hand what they build up with the other, and give themselves the lie, and tempt men to think that all religion is a delusion; but those who speak from experience, who live up to what they preach, are truly great; they honour God, and God will honour them (Sa1 2:30), and hereafter they shall shine as the stars in the kingdom of our Father.

II. The righteousness which Christ came to establish by this rule, must exceed that of the scribes and Pharisees, Mat 5:20. This was strange doctrine to those who looked upon the scribes and Pharisees as having arrived at the highest pitch of religion. The scribes were the most noted teachers of the law, and the Pharisees the most celebrated professors of it, and they both sat in Moses' chair (Mat 23:2), and had such a reputation among the people, that they were looked upon as super-conformable to the law, and people did not think themselves obliged to be as good as they; it was therefore a great surprise to them, to hear that they must be better than they, or they should not go to heaven; and therefore Christ here avers it with solemnity; I say unto you, It is so. The scribes and Pharisees were enemies to Christ and his doctrine, and were great oppressors; and yet it must be owned, that there was something commendable in them. They were much in fasting and prayer, and giving of alms; they were punctual in observing the ceremonial appointments, and made it their business to teach others; they had such an interest in the people that they ought, if but two men went to heaven, one would be a Pharisee; and yet our Lord Jesus here tells his disciples, that the religion he came to establish, did not only exclude the badness, but excel the goodness, of the scribes and Pharisees. We must do more than they, and better than they, or we shall come short of heaven. They were partial in the law, and laid most stress upon the ritual part of it; but we must be universal, and not think it enough to give the priest his tithe, but must give God our hearts. They minded only the outside, but we must make conscience of inside godliness. They aimed at the praise and applause of men, but we must aim at acceptance with God: they were proud of what they did in religion, and trusted to it as a righteousness; but we, when we have done all, must deny ourselves, and say, We are unprofitable servants, and trust only to the righteousness of Christ; and thus we may go beyond the scribes and Pharisees.

Matthew Henry (1662–1714) — Commentary on the Whole Bible. This section covers verses 17–20. Public domain.
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Hilary of PoitiersAD 367
From the expression here used, “pass,” we may suppose that the constituting elements of heaven and earth shall not be annihilated.
Or, He calls the passion, and the cross, the least, which if one shall not confess openly, but be ashamed of them, he shall be least, that is, last, and as it were no man; but to him that confesses it He promises the great glory ofa heavenly calling.
Hilary of PoitiersAD 367
Commentary on Matthew 4.16
With a beautiful introduction Christ moves beyond the work of the law. He does not intend to abolish it but to enhance it by fulfilling it. He declares that his apostles will not be able to enter heaven unless their righteousness exceeds that of the Pharisees. Therefore he bypasses what is laid down in the law, not for the sake of abolishing it, but for the sake of fulfilling it.
Hilary of Poitiers (as quoted by Aquinas, AD 1274)AD 367
Catena Aurea by Aquinas
He means not that we should seek glory of men, but that though we conceal it, our work may shine forth in honour of God to those among whom we live.

From the expression here used pass, we may suppose that the constituting elements of heaven and earth shall not be annihilatedb.

Or, He calls the passion, and the cross, the least, which if one shall not confess openly, but be ashamed of them, he shall be least, that is, last, and as it were no man; but to him that confesses it He promises the great glory of a heavenly calling.
John Chrysostom (as quoted by Aquinas, AD 1274)AD 407
Catena Aurea by Aquinas
(Hom. xvi.) Christ then fulfilled the Prophets by accomplishing what was therein foretold concerning Himself—and the Law, first, by transgressing none of its precepts; secondly, by justifying by faith, which the Law could not do by the letter.

He speaks not this of the old laws, but of those which He was now going to enact, of which he says, the least, though they were all great. For as He so oft spoke humbly of Himself, so does He now speak humbly of His precepts.

Or, when you hear the words, least in the kingdom of heaven, imagine nothing less than the punishment of hell. For He oft uses the word 'kingdom,' not only of the joys of heaven, but of the time of the resurrection, and of the terrible coming of Christ.
John ChrysostomAD 407
Homily on the Gospel of Matthew 16
"Whosoever therefore shall break one of these least commandments, and shall teach men so, he shall be called least in the kingdom of Heaven."

Thus, having rid Himself of the evil suspicion, and having stopped the mouths of them who would fain gainsay, then at length He proceeds to alarm, and sets down a heavy denunciation in support of the enactments He was entering on.

For as to His having said this in behalf not of the ancient laws, but of those which He was proceeding to enact, listen to what follows, "For I say unto you," saith he, "Except your righteousness shall exceed the righteousness of the Scribes and Pharisees, ye shall in no case enter into the kingdom of Heaven."

For if He were threatening with regard to the ancient laws, how said He, "except it shall exceed?" since they who did just the same as those ancients, could not exceed them on the score of righteousness.

But of what kind was the required excess? Not to be angry, not even to look upon a woman unchastely.

For what cause then doth He call these commandments "least," though they were so great and high? Because He Himself was about to introduce the enactment of them; for as He humbled Himself, and speaks of Himself frequently with measure, so likewise of His own enactments, hereby again teaching us to be modest in everything. And besides, since there seemed to be some suspicion of novelty, He ordered His discourse for a while with reserve.

But when thou hearest, "least in the kingdom of Heaven," surmise thou nothing but hell and torments. For He was used to mean by "the kingdom," not merely the enjoyment thereof, but also the time of the resurrection, and that awful coming. And how could it be reasonable, that while he who called his brother fool, and transgressed but one commandment, falls into hell; the breaker of them all, and instigator of others to the same, should be within the kingdom. This therefore is not what He means, but that such a one will be at that time least, that is, cast out, last. And he that is last will surely then fall into hell. For, being God, He foreknew the laxity of the many, He foreknew that some would think these sayings were merely hyperbolical, and would argue about the laws, and say, What, if any one call another a fool, is he punished? If one merely look on a woman, doth he become an adulterer? For this very cause He, destroying such insolence beforehand, hath set down the strongest denunciation against either sort, as well them who transgress, as them who lead on others so to do.

"But whosoever shall do and teach," saith He, "shall be called great."

For not to ourselves alone, should we be profitable, but to others also; since neither is the reward as great for him who guides himself aright, as for one who with himself adds also another. For as teaching without doing condemns the teacher (for "thou which teachest another," it is said, "teachest thou not thyself"?) so doing but not guiding others, lessens our reward. One ought therefore to be chief in either work, and having first set one's self right, thus to proceed also to the care of the rest. For on this account He Himself hath set the doing before the teaching; to intimate that so most of all may one be able to teach, but in no other way. For one will be told, "Physician, heal thyself." Since he who cannot teach himself, yet attempts to set others right, will have many to ridicule him. Or rather such a one will have no power to teach at all, his actions uttering their voice against him. But if he be complete in both respects, "he shall be called great in the kingdom of Heaven."
JeromeAD 420
Commentary on Matthew
(Verse 19 and following) Therefore, whoever shall break one of the least of these commandments, and shall teach men so, he shall be called the least in the kingdom of heaven: but he who shall do and teach them, the same shall be called great in the kingdom of heaven. For I say to you, that unless your justice exceeds that of the scribes and Pharisees, you shall not enter into the kingdom of heaven. You have heard that it was said to those of old: You shall not kill; and whoever kills shall be liable to judgment. But I tell you. This chapter, sticking with the previous testimony, in which he said: Not one iota, or one apex, will pass from the Law, until all things are fulfilled. Therefore, he seals the Pharisees, who, despising the commandments of God, establish their own traditions, which do not benefit them in teaching the people if they destroy even a small thing that is commanded in the Law. However, we can also understand that the education of teachers, even if subject to a small sin, leads them down from the highest rank, and it does not benefit them to teach righteousness, which the smallest fault destroys. And let perfect happiness be to fulfill with action what you have taught in words.
Jerome (as quoted by Aquinas, AD 1274)AD 420
Catena Aurea by Aquinas
This head is closely connected with the preceding. It is directed against the Pharisees, who, despising the commandments of God, set up traditions of their own, and means that their teaching the people would not avail themselves, if they destroyed the very least commandment in the Law. We may take it in another sense. The learning of the master if joined with sin however small, loses him the highest place, nor does it avail any to teach righteousness, if he destroys it in his life. Perfect bliss is for him who fulfils in deed what he teaches in word.
Augustine of Hippo (as quoted by Aquinas, AD 1274)AD 430
Catena Aurea by Aquinas
(ubi sup.) Or, the precepts of the Law are called 'the least,' as opposed to Christ's precepts which are great. The least commandments are signified by the iota and the point. He, therefore, who breaks them, and teaches men so, that is, to do as he does, shall be called least in the kingdom of heaven. Hence we may perhaps conclude, that it is not true that there shall none be there except they be great.

(ubi sup.) Otherwise; he who breaks the least of these commandments, that is, of Moses' Law, and teaches men so, shall be called the least; but he who shall do (these least), and so teach, shall not indeed be esteemed great, yet not so little as he who breaks them. That he should be great, he ought to do and to teach the things which Christ now teaches.
Augustine of HippoAD 430
Hence it is the least commandments that are meant by one iota and one tittle. And therefore, whosoever shall break and shall teach [men] so,— i.e. in accordance with what he breaks, not in accordance with what he finds and reads—shall be called the least in the kingdom of heaven; and therefore, perhaps, he will not be in the kingdom of heaven at all, where only the great can be. But whosoever shall do and teach [men] so, — i.e. who shall not break, and shall teach men so, in accordance with what he does not break—shall be called great in the kingdom of heaven. But in regard to him who shall be called great in the kingdom of heaven, it follows that he is also in the kingdom of heaven, into which the great are admitted: for to this what follows refers.
Cyril of AlexandriaAD 444
FRAGMENT 48.19
Whoever sets aside “one of the least of the commandments” of the law is set aside by God as God’s enemy and as an inventor of laws opposed to God. And now out of the law of the gospel that one receives the retribution which, under the ancient law, was not defined. For this reason Christ fittingly says, “I am not come to destroy but to fulfill.” For that which then was lacking, here is made full. It is said in the law: “Stand in the presence of the elderly” and “If you see the beast of your enemy fallen under its load, go help him lift it up.” If anyone transgressed these commandments, there was no retribution specified under the law. So Christ makes up this lack when he says that in the kingdom of heaven such a person will be treated with scorn.
Pseudo-Chrysostom (as quoted by Aquinas, AD 1274)AD 500
Catena Aurea by Aquinas
And that for two reasons. First, that by these words He might admonish His disciples, that as He fulfilled the Law, so they should strive to fulfil it. Secondly, because the Jews would falsely accuse them as subverting the Law, therefore he answers the calumny beforehand, but in such a manner as that He should not be thought to come simply to preach the Law as the Prophets had done.

But since all things which should befal from the very beginning of the world to the end of it, were in type and figure foreshewn in the Law, that God may not be thought to be ignorant of any of those things that take place, He therefore here declares, that heaven and earth should not pass till all things thus foreshewn in the Law should have their actual accomplishment.

If even an honourable man blushes to be found in a falsehood, and a wise man lets not fall empty any word he has once spoken, how could it be that the words of heaven should fall to the ground empty? Hence He concludes, Whoso shall break the least of these commandments, &c. And, I suppose, the Lord goes on to reply Himself to the question, Which are the least commandments? Namely, these which I am now about to speak.

Otherwise; the precepts of Moses are easy to obey; Thou shall not kill. Thou shall not commit adultery. The very greatness of the crime is a check upon the desire of committing it; therefore the reward of observance is small, the sin of transgression great. But Christ's precepts, Thou shalt not be angry, Thou shalt not lust, are hard to obey, and therefore in their reward they are great, in their transgression, 'least.' It is thus He speaks of these precepts of Christ, such as Thou shall not be angry, Thou shalt not lust, as 'the least;' and they who commit these lesser sins, are the least in the kingdom of God; that is, he who has been angry and not sinned grievously is secure from the punishment of eternal damnation; yet he does not attain that glory which they attain who fulfil even these least.
Remigius of Rheims (as quoted by Aquinas, AD 1274)AD 533
Catena Aurea by Aquinas
He here asserts two things; He denies that He was come to subvert the Law, and affirms that He was come to fulfil it.

Amen is a Hebrew word, and may be rendered in Latin, 'vere,' 'fidenter,' or 'fiat;' that is, 'truly,' 'faithfully,' or 'so be it.' The Lord uses it either because of the hardness of heart of those who were slow to believe, or to attract more particularly the attention of those that did believe.

But shall abide in their essence, but pass through renewal.
Gregory the Dialogist (as quoted by Aquinas, AD 1274)AD 604
Catena Aurea by Aquinas
(Hom. in Ev. xii. 1.) Or, by the kingdom of heaven is to be understood the Church, in which that teacher who breaks a commandment is called least, because he whose life is despised, it remains that his preaching be also despised.
Rabanus Maurus (as quoted by Aquinas, AD 1274)AD 856
Catena Aurea by Aquinas
He fitly mentions the Greek iota, and not the Hebrew jod, because the iota stands in Greek for the number ten, and so there is an allusion to the Decalogue of which the Gospel is the point and perfection.
Rabanus MaurusAD 856
He fitly mentions the Greek iota, and not the Hebrew job, because the iota stands in Greek for the number ten, and so there is an allusion to the Decalogue of which the Gospel is the point and perfection.
Theophylact of OhridAD 1107
The "least commandments" are those which He Himself is about to give, not those of the law of Moses. He calls them "least" out of humility, to instruct you, O reader, to have moderate thoughts of yourself as you give your teachings. He who "shall be called least in the kingdom of heaven" means he who will be last in the resurrection and who will be cast into gehenna. For such a one shall not enter the kingdom of heaven, far from it! By "kingdom" understand the resurrection.

First Christ says, "whosoever shall do," and then, "and shall teach"; for how can I guide another along a road that I have not myself travelled? By the same token, if I practice the commandments, but do not teach them, my reward is not so great. There can even be condemnation, if I do not teach because of spite or sloth.
Glossa Ordinaria (as quoted by Aquinas, AD 1274)AD 1274
Catena Aurea by Aquinas
(ord.) Having now exhorted His hearers to undergo all things for righteousness' sake, and also not to hide what they should receive, but to learn more for others' sake, that they may teach others, He now goes on to tell them what they should teach, as though He had been asked, 'What is this which you would not have hid, and for which you would have all things endured? Are you about to speak any thing beyond what is written in the Law and the Prophets;' hence it is He says, Think not that I am come to subvert the Law or the Prophets.

(ord.) By 'break,' is meant, the not doing what one understands rightly, or the not understanding what one has corrupted, or the destroying the perfectness of Christ's additions.
Source: Quotations drawn from early Church Fathers and historical Christian theologians (AD 100–1500). Some quotes address the surrounding passage context rather than this verse alone.
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