Matthew 5:25

Agree with your adversary quickly, while you are with him on the way; lest perhaps the prosecutor deliver you to the judge, and the judge deliver you to the officer, and you be cast into prison.

World English Bible
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WEBBE

Agree with your adversary quickly while you are with him on the way; lest perhaps the prosecutor deliver you to the judge, and the judge deliver you to the officer, and you be cast into prison.

BSB

Reconcile quickly with your adversary, while you are still on the way to court. Otherwise, he may hand you over to the judge, and the judge may hand you over to the officer, and you may be thrown into prison.

KJV

Agree with thine adversary quickly, whiles thou art in the way with him; lest at any time the adversary deliver thee to the judge, and the judge deliver thee to the officer, and thou be cast into prison.

ASV

Agree with thine adversary quickly, while thou art with him in the way; lest haply the adversary deliver thee to the judge, and the judge deliver thee to the officer, and thou be cast into prison.

BBE

Come to an agreement quickly with him who has a cause against you at law, while you are with him on the way, for fear that he may give you up to the judge and the judge may give you to the police and you may be put into prison.

Original Greek

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The early church

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)
(ubi sup.) If this direction be taken literally, it might lead some to suppose that this ought indeed to be so done if our brother is present, for that no long time can be meant when we are bid to leave our offering there before the altar. For if he be absent, or possibly beyond sea, it is absurd to suppose that the offering must be left before the altar; to be offered after we have gone over land and sea to seek him. Wherefore we must embrace an inward, spiritual sense of the whole, if we would understand it without involving any absurdity. The gift which we offer to God, whether learning, or speech, or whatever it be, cannot be accepted of God unless it be supported by faith. If then we have in aught harmed a brother, we must go and be reconciled with him, not with the bodily feet, but in thoughts of the heart, when in humble contrition you may cast yourself at your brother's feet in sight of Him whose offering you are about to offer. For thus in the same manner as though He were present, you may with unfeigned heart seek His forgiveness; and returning thence, that is, bringing back again your thoughts to what you had first begun to do, may make your offering. (Serm. in Mont. i. 11.) Let us see who this adversary is to whom we are bid to be benevolent, It may then be either the Devil, or man, or the flesh, or God, or His commandments. But I do not see how we can be bid be benevolent, or agreeing with the Devil; for where there is good will, there is friendship, and no one will say that friendship should be made with the Devil, or that it is well to agree with him, having once proclaimed war against him when we renounced him; nor ought we to consent with him, with whom had we never consented, we had never come into such circumstances, (ubi sup.) I do not see again how it can be understood of man. For how can man be said to deliver us to the Judge, when we know only Christ as the Judge, before whose tribunal all must be sisted. How then can he deliver to the Judge, who has himself to appear before Him? Moreover if any has sinned against any by killing him, he has no opportunity of agreeing with him in the way, that is in this life; and yet that hinders not but that he may be rescued from judgment by repentance. Much less do I see how we can be bid be agreeing with the flesh; for they are sinners rather who agree with it; but they who bring it into subjection, do not agree with it, but compel it to agree with them. (ubi sup.) Perhaps then it is God with whom we are here enjoined to agree. He may be said to be our adversary, because we have departed from Him by sin, and He resisteth the proud. Whosoever then shall not have been reconciled in this life with God through the death of His Son, shall be by Him delivered to the Judge, that is, the Son, to whom He has committed all judgment. And man may be said to be in the way with God, because He is every where. But if we like not to say that the wicked are with God, who is every where present, as we do not say that the blind are with that light which is every where around them, there only remains the law of God which we can understand by our adversary. For this law is an adversary to such as love to sin, and is given us for this life that it may be with us in the way. To this we ought to agree quickly, by reading, hearing, and bestowing on it the summit of authority, and that when we understand it, we hate it not because it opposes our sins, but rather love it because it corrects them; and when it is obscure, pray that we may understand it.
Augustine of Hippo · d. 430Catena 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.