Matthew 5:26

Most certainly I tell you, you shall by no means get out of there, until you have paid the last penny.

World English Bible
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WEBBE

Most certainly I tell you, you shall by no means get out of there until you have paid the last penny.

BSB

Truly I tell you, you will not get out until you have paid the last penny.

KJV

Verily I say unto thee, Thou shalt by no means come out thence, till thou hast paid the uttermost farthing.

ASV

Verily I say unto thee, Thou shalt by no means come out thence, till thou have paid the last farthing.

BBE

Truly I say to you, You will not come out from there till you have made payment of the very last farthing.

Original Greek

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The early church

(ubi sup.) By the Judge I understand Christ, for, the Father hath committed all judgment to the Son; (John 5:22.) and by the officer, or minister, an Angel, for, Angels came and ministered unto Him; and we believe that He will come with his Angels to judge. (ubi sup.) By the prison I understand the punishment of the darkness. And that none should despise that punishment, He adds, Verily I say unto thee, thou shalt not come out thence till thou hast paid the very last farthing. (ubi sup.) Or it is an expression to denote that there is nothing that shall go unpunished; as we say 'To the dregs,' when we are speaking of any thing so emptied that nothing is left in it. Or by the last farthing (quadrans.) may be denoted earthly sins. For the fourth and last element of this world is earth. Paid, that is in eternal punishment; and until used in the same sense as in that, Sit thou on my right hand until I make thy enemies thy footstool; (Ps. 110:1.) for He does not cease to reign when His enemies are put under His feet. So here, until thou hast paid, is as much as to say, thou shalt never come out thence, for that he is always paying the very last farthing while he is enduring the everlasting punishment of earthly sins.
Augustine of Hippo · d. 430Catena Aurea (Aquinas, 1274)
The Lord suffers us at no time to be wanting in peaceableness of temper, and therefore bids us be reconciled to our adversary quickly, while on the road of life, lest we be cast into the season of death before peace be joined between us. Or, the adversary delivers you to the Judge, when the abiding of your wrath towards him convicts you. For because charity covereth a multitude of sins, we shall therefore pay the last farthing of punishment, unless by the expense of charity we redeem the fault of our sin.
Hilary of Poitiers · d. 367Catena Aurea (Aquinas, 1274)
"Agree with thine adversary quickly, whilst thou art in the way with him." That is, that thou mayest not say, "What then, if I am injured;" "what if I am plundered, and dragged too before the tribunal?" even this occasion and excuse He hath taken away: for He commands us not even so to be at enmity. Then, since this injunction was great, He draws His advice from the things present, which are wont to restrain the grosser sort more than the future. "Why, what sayest thou?" saith He. "That thine adversary is stronger, and doeth thee wrong? Of course then he will wrong thee more, if thou do not make it up, but art forced to go into court. For in the former case, by giving up some money, thou wilt keep thy person free; but when thou art come under the sentence of the judge, thou wilt both be bound, and pay the utmost penalty. But if thou avoid the contest there, thou wilt reap two good results: first, not having to suffer anything painful: and secondly, that the good done will be thereafter thine own doing, and no longer the effect of compulsion on his part. But if thou wilt not be ruled by these sayings, thou wrongest not him, so much as thyself." And see here also how He hastens him; for having said, "Agree with thine adversary," He added, "quickly;" and He was not satisfied with this, but even of this quickness He hath required a further increase, saying, "Whilst thou art in the way with him;" pressing and hastening him hereby with great earnestness. For nothing doth so much turn our life upside down, as delay and procrastination in the performance of our good works. Nay, this hath often caused us to lose all. Therefore, as Paul for his part saith, "Before the sun set, do away the enmity;" and as He Himself had said above, "Before the offering is completed, be reconciled;" so He saith in this place also, "Quickly, whilst thou art in the way with him," before thou art come to the doors of the court; before thou standest at the bar and art come to be thenceforth under the sway of him that judgeth. Since, before entering in, thou hast all in thine own control but if thou set thy foot on that threshold, thou wilt not by ever so earnest efforts be able to arrange thy matters at thy will, having come under the constraint of another. But what is it "to agree?" He means either, consent rather to suffer wrong; or, "so plead the cause, as if thou wert in the place of the other;" that thou mayest not corrupt justice by self-love, but rather, deliberating on another's cause as thine own, mayest so proceed to deliver thy vote in this matter. And if this be a great thing, marvel not; since with this view did He set forth all those His blessings, that having beforehand smoothed and prepared the hearer's soul, he might render it apter to receive all His enactments. Now some say that He obscurely signifies the devil himself, under the name of the adversary; and bids us have nothing of his, (for this, they say, is to "agree" with him): no compromise being possible after our departure hence, nor anything awaiting us, but that punishment, from which no prayers can deliver. But to me He seems to be speaking of the judges in this world, and of the way to the court of justice, and of this prison. For after he had abashed men by higher things, and things future, he alarms them also by such as are in this life. Which thing Paul also doth, using both the future and the present to sway his hearer: as when, deterring from wickedness, he points out to him that is inclined to evil, the ruler armed: thus saying, "But if thou do that which is evil, be afraid; for he beareth not the sword in vain; for he is a minister of God." And again, enjoining us to be subject unto him, he sets forth not the fear of God only, but the threatening also of the other party, and his watchful care. "For ye must needs be subject, not only for wrath, but also for conscience sake." Because the more irrational, as I have already said, are wont to be sooner corrected by these things,
John Chrysostom · d. 407Homilies on Matthew
The word here in our Latin books is 'consentiens,' in Greek, εὐνοῶν, which means, 'kind,' 'benevolent.' Some, from that verse of Peter, Your adversary the Devil, &c. (1 Pet. 5:8.) will have the Saviour's command to be, that we should be merciful to the Devil, not causing him to endure punishment for our sakes. For as he puts in our way the incentives to vice, if we yield to his suggestions, he will be tormented for our sakes. Some follow a more forced interpretation, that in baptism we have each of us made a compact with the Devil by renouncing him. If we observe this compact, then we are agreeing with our adversary, and shall not be cast into prison. And how can the body be cast into prison if it agree not with the spirit, seeing soul and body must go together, and that the flesh can do nothing but what the soul shall command? But from the context the sense is manifest; the Lord is exhorting us to peace and concord with our neighbour; as it was said above, Go, be reconciled to thy brother. A farthing is a coin containing two mites. What He says then is, 'Thou shalt not go forth thence till thou hast paid for the smallest sins.'
Jerome · d. 420Catena Aurea (Aquinas, 1274)
The Lord is urgent with us to hasten to make friends with our enemies while we are yet in this life, knowing how dangerous for us that one of our enemies should die before peace is made with us. For if death bring us while yet at enmity to the Judge, he will deliver us to Christ, proving us guilty by his judgment. Our adversary also delivers us to the Judge, when he is the first to seek reconciliation; for he who first submits to his enemy, brings him in guilty before God. The officer, that is, the ministering Angel of punishment, and he shall cast you into the prison of hell. Or, If you will make your peace yet in this world, you may receive pardon of even the heaviest offences; but if once damned and cast, into the prison of hell, punishment will be exacted of you not for grievous sins only, but for each idle word, which may be denoted by the very last farthing. Or, the prison is worldly misfortune which God often sends upon sinners.
Pseudo-Chrysostom · d. 500Catena Aurea (Aquinas, 1274)

Commentary

Matthew Henry · Verses 21–26

The Jewish teachers had taught, that nothing except actual murder was forbidden by the sixth commandment. Thus they explained away its spiritual meaning. Christ showed the full meaning of this commandment; according to which we must be judged hereafter, and therefore ought to be ruled now. All rash anger is heart murder. By our brother, here, we are to understand any person, though ever so much below us, for we are all made of one blood. "Raca," is a scornful word, and comes from pride: "Thou fool," is a spiteful word, and comes from hatred. Malicious slanders and censures are poison that kills secretly and slowly. Christ told them that how light soever they made of these sins, they would certainly be called into judgment for them. We ought carefully to preserve Christian love and peace with all our brethren; and if at any time there is a quarrel, we should confess our fault, humble ourselves to our brother, making or offering satisfaction for wrong done in word or deed: and we should do this quickly; because, till this is done, we are unfit for communion with God in holy ordinances. And when we are preparing for any religious exercises, it is good for us to make that an occasion of serious reflection and self-examination. What is here said is very applicable to our being reconciled to God through Christ. While we are alive, we are in the way to his judgement-seat; after death, it will be too late. When we consider the importance of the case, and the uncertainty of life, how needful it is to seek peace with God, without delay!

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Cross-references: Treasury of Scripture Knowledge. Hebrew and Greek data from STEPBible.org (Tyndale House, Cambridge), CC BY 4.0. Library: sources.