Matthew 5:19

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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Augustine of Hippo

AD 430
Serm. in Mont., i, 8: In this last sentence again there is a double sense; to fulfil the Law, either by adding something which it had not, or by doing what it commands. cont. Faust., 19, 7. et seq.: And lastly, because even for them who were undergrace, it was hard in this mortal life to fulfil that of the Law, “Thou shaltnot lust,” He being made a Priest by the sacrifice of His flesh, obtained forus this indulgence, even in this fulfilling the Law, that where through our infirmity we could not, we should be strengthened through His perfection, of whom as our head we all are members. For so I think must be taken these words, "to fulfil” the Law, by adding to it, that is, such things as either contribute to the explanation of the old glosses, or to enable to keep them. For the Lord has showed us that even a wicked motion of the thoughts to the wrong of a brother is to be accounted a kind of murder. The Lord also teaches us, that it is better to keep near to the truth without swearing, t...

Augustine of Hippo

AD 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 Alexandria

AD 444
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. ...

George Leo Haydock

AD 1849
He shall be called; i.e. (by a frequent Hebrew idiom) he shall be the least in the kingdom of heaven; that is, according to St. Augustine he shall not be there at all; for none but the great in sanctity and virtue shall find admittance into heaven. (Witham) Do not then imitate the Scribes and Pharisees, who content themselves with instructing other in the precepts of the law, without practising them themselves, or if they observe the letter, neglect the spirit of the law, performing what it ordains, not to please God, but to satisfy their vanity. (Calmet) ...
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Glossa Ordinaria

AD 1480
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.
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Gregory The Dialogist

AD 604
Hom. in Ev., 12, 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.
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Hilary of Poitiers

AD 368
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. ...
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Hilary of Poitiers

AD 368
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. ...
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AD 420
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. ...
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John Chrysostom

AD 407
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, says He, Unless your righteousness shall exceed the righteousness of the Scribes and Pharisees, you 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 does He call these commandments least, though they were so great and high? Because He Himself was about to introduce the enac...
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John Chrysostom

AD 407
For what reason then does he call some of these commandments “least,” though they are so magnificent and lofty? Jesus spoke this way because he was about to introduce his own teaching as a new law. As he humbles himself and speaks of himself with great modesty, so he refers to his own teaching in the same manner. In this way Jesus teaches us to practice humility in everything. And besides, since some suspected his teaching to be a new departure, he temporarily taught it in a more reserved way. But when you hear “least in the kingdom of heaven,” you are to think of nothing but hell and punishment. For it was his practice to speak not only of the joy the kingdom brings but also of the time of the resurrection and the fearful event of the second coming. Think of one who calls a brother a fool. That one transgresses only one commandment, maybe even the slightest one, and falls into hell. Compare that one with another who breaks all the commandments and instigates others to break them. Do b...

John Chrysostom

AD 407
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. Hom. 16: 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. But since all things which should befall 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...
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Rabanus Maurus

AD 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.
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Remigius of Rheims

AD 533
He here asserts two things; He denies that He was come to subvert the Law, and affirms that He was come to fulfil it. But shall abide in their essence, but “pass” through renewal.
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Theophylact of Ochrid

AD 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. ...

Knowing this first, that no prophecy of the scripture is of any private interpretation. - 2 Peter 1:20

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