The interpretation timeline
Matthew 5:25 Douay-Rheims

Be at agreement with thy adversary betimes, whilst thou art in the way with him: lest perhaps the adversary deliver thee to the judge, and the judge deliver thee to the officer, and thou be cast into prison.

A.D. 367 – 1871 9 witnesses 20 excerpts

Patristic

before A.D. 750
367
A.D.
Hilary of Poitiers Patristic
c. A.D. 310–367
“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.”
407
A.D.
John Chrysostom Patristic
A.D. 347–407
“Or, He here speaks of the judges of this world, of the way which leads to this judgment, and of human prisons; thus not only employing future but present inducements, as those things which are before the eyes affect us most, as St. Paul also declares, If thou doest evil fear the power, for he beareth not the sword in vain. (Rom. 13:4.)”
Source
420
A.D.
Jerome Patristic
c. A.D. 347–420
“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.”
Source
“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.”
430
A.D.
Augustine of Hippo Patristic
A.D. 354–430
“(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,”
Source
“(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.”
Source
“(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.”
Source
“(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.”

Scholastic

c. 1100 – 1500
1256
A.D.
Thomas Aquinas Catholic
1225–1274
“"If therefore you offer." Here he forbids inveterate anger, from which hatred is born, and he argues from the greater, according to Rabanus, thus: if it is not lawful for you to be angry with your brother, much more is it not lawful to retain anger, whence hatred is born. Therefore "if you offer," that is, if you propose to offer, "at the altar." This is explained in many ways, according as "altar" is sometimes taken for the material temple, as in Psalm 25:6: "I will wash my hands among the innocent, and I will encompass your altar, O Lord." Sometimes it is taken for Christ; Lamentations 2:7: "The Lord has cast off his altar," that is, Christ, namely in the Passion. Sometimes for the devotion of the heart, and this is the interior temple, according to Augustine. As to the first, "if you offer your gift," that is, your oblation, "at the altar" — the material altar, taken literally; or the gift of a good work, according to the Gloss, "at the altar," that is, Christ. Or, according to Augustine: "your gift," that is, prayers, Psalms, hymns, and the like, "at the altar," that is, in the heart, which is the temple where you are about to offer; and "there," namely in the Church, or in the heart, "you remember that your brother has something against you." This can be understood in two ways, namely concerning the one who injures and the one who is injured. Concerning the one who injures, thus, according to Augustine: "if you remember," that is, if it comes into your mind and to your knowledge, that "your brother," whom you have injured, "has something against you" — namely on account of the disposition of an insult, of bodily injury, of the taking away of temporal goods, of the blackening of reputation — "leave there," namely before the altar, or before God, "your gift, and go": if he is absent, not with the feet of the body, as Augustine says, but you should prostrate yourself in humble mind in the sight of him to whom you are about to offer; if he is present, he must be called back to love, by seeking pardon from him. Or, if "your brother," who injured you, "has something against you," that is, whereby he is set against you, "go to be reconciled to your brother," by giving up your rancor toward him. For from the very fact that, in saying "if your brother has something against you," he does not add "justly," he gives us to understand that even the one to whom the injury was done ought to seek friendship. Hence Chrysostom says: if for the glory of your salvation the Lord commands you to make friendship, much more ought you to ask for it, so that you may attain a double glory: one, because you are innocent; the other, because you asked first. "And then, coming" — as one now pleasing to the Lord, whereas before you did not please him — "you shall offer your gift." Chrysostom: if you have offended in thought, be reconciled in thought; if in words, in words; if in deeds, in deeds. And again: unless you appease by deeds the one whom you have injured by deeds, you pray to the Lord in vain, you give alms in vain from the things by which you have despoiled others. For what does it profit if one man prays to the Lord for you, and another cries out to the Lord against you? Ecclesiasticus 34:23: "The Most High does not approve the gifts of the wicked." And note here four things which are required for the giving or offering: first, cheerfulness of mind; hence he says "if you offer"; Ecclesiasticus 35:11: "In every gift make your countenance cheerful." Second, ownership of the thing; hence he says "your gift"; Proverbs 3:9: "Honor God with your substance." Third, the fitness of the place, "at the altar." Fourth, love of neighbor; hence he says "and you remember"; 1 Corinthians 13:3: "If I distribute all my goods to feed the poor, but have not charity, it profits me nothing." He is foolish who loses an abundance of food for the sake of a penny's worth of salt, that is, of charity, which gives savor and beauty to all things, as gold does to other metals. "Be at agreement with your adversary." Above he forbade having anger, or discord, with one's brothers; here he removes having discord with an adversary, saying "be agreeing," that is, benevolent or kindly — as is gathered from the Greek, as Jerome says — "with your adversary." An objection: the Devil is an adversary; therefore one must agree with him. Response: he speaks of the one who is with us on the way; but the Devil is not on the way, nor can he be, but is in eternal straying from the way; hence "your adversary," according to Chrysostom, means a man who opposes, or literally an enemy; Romans 12:18: "If it be possible, as much as is in you, having peace with all men." "While," that is, until, "you are with him in the way," that is, in the state of meriting; John 9:4: "The time is coming when no one can work." Or our adversary is God, of whom Exodus 23:7 says: "I am the Lord, who am an adversary to the wicked." Or it is the divine word, which is opposed to those willing to sin; 2 Timothy, penultimate chapter, 16: "All Scripture, divinely inspired, is useful for teaching, for reproving." Or it is the remorseful conscience, of which Psalm 49:21 says: "I will reprove you, and set myself against your face." And thus, again, it is explained according to all these ways. Hence, "be agreeing with your adversary," that is, with God, and with the divine word, according to Augustine and Bede, with whom one must agree in the hope of the promise, in the fear of punishment, in the carrying out of the precept, in the avoidance of what is forbidden. "Quickly," that is, without delay; Ecclesiasticus 5:8: "Do not delay to be converted to the Lord." "While you are with him," that is, with him with whom you shall walk rightly "in the way," namely the way of Christ, or of penance, or of the world; Psalm 118:32: "I have run the way of your commandments, when you enlarged my heart." "Lest perhaps he deliver you." According to Augustine, "lest perhaps" means lest it become, as it were by occasion, the cause of your being delivered up. And he says "perhaps," according to the Gloss, lest the place of repentance be taken away. For if the adversary had died before he agreed — or had been well-disposed — it would seem that he would be condemned, were it said simply and without qualification, "lest the adversary" — that is, the divine word, or God, or the remorseful conscience — "deliver you to the judge." The Gloss: into the hands of Christ. John 5:22: "he has given all judgment to the Son." And "the judge" is Christ; Jeremiah 29:23: "I am the judge, and the witness." "Deliver you to the officer": the Gloss says, that is, to the Angel who gathers the tares in order to seize them, below, chapter 13; Psalm 103:4: "who makes his Angels spirits." Or "to the officer," that is, to the Devil, the exactor; Isaiah 14:4: "How has the exactor ceased?" "And you be cast into prison," that is, into the abyss of Hell; Isaiah 24:22: "they shall be shut up in prison"; Revelation 20:3: "he cast him into the abyss, and shut him up." "Amen I say to you," that is, know for certain, that you shall not go out from there, "until" — the Gloss: that is, never. Hence Augustine: "until" does not here signify the end of the punishment, but the continuation of the misery. As if he were to say: you shall always be paying, and never fully pay off; as in Psalm 109:1: "Sit at my right hand, until I make your enemies your footstool," that is, you shall sit forever. "You pay the last farthing," that is, the smallest sins, according to Bede and Rabanus, because nothing will remain unpunished — for the farthing is a kind of coin having two mites. Or, according to Augustine and Jerome, by "farthing" he meant to signify earthly sins: for the last farthing is earth, which is the fourth part of the elements of this world, and the last from fire; as if he were to say: because you were unwilling to be fire through charity, air through the vigor of good work, water through the sanctification of Baptism, but were earthly by clinging to earthly things, you shall not go out from there, because you shall never fully pay off the sins which you contracted from the earth.”

Post-Reformation

c. 1650 – 1900
1771
A.D.
John Gill Reformed
1697–1771
“Agree with thine adversary quickly,.... These words are not to be understood in an allegorical sense, as if "the adversary" was the justice of God, demanding payment of debts; "the way", this present life; "the judge", God himself; "the officer", the devil; "the prison", the pit of hell; and "the uttermost farthing", the least sin, which will never be remitted without satisfaction: but the design of them is to prevent lawsuits about debts, which may be in dispute; it being much better for debtor and creditor, especially the former, to compose such differences among themselves, than to litigate the matter in a court of judicature. By "the adversary" is meant not an enemy, one that bears hatred and ill will, but a brother that has ought against a man; a creditor, who demands and insists upon payment of what is owing to him; and for this purpose has taken methods towards bringing the debtor before a proper magistrate, in order to oblige him to payment: wherefore it is better for him to make up and agree the matter directly, as soon as possible, whilst thou art in the way with him; that is, whilst the creditor and debtor are going together to some inferior magistrate, or lesser court, as the sanhedrim, which consisted of three persons only, before whom such causes might be tried: for , pecuniary causes, or causes relating to money matters, were tried "by the bench of three" (g): and the selfsame advice is given in the Talmud (h), as here, where it seems to be a common proverb; for it is said, "there are men that say, or men usually say, , "whilst thou art in the way with thine adversary, be obedient".'' Lest at any time the adversary should deliver thee to the judge, a superior magistrate in a higher court; for if the creditor would, he could oblige the debtor to go with him to the supreme court of judicature, and try the cause there; for so say the Jewish (i); canons: "if the creditor says we will go to the great sanhedrim, they compel the debtor, and he goes up with them, as it is said, "the borrower is servant to the lender",'' where it might go harder with the poor debtor; and therefore it was advisable to prevent it by an agreement, lest the judge deliver thee to the officer, and thou be cast into prison, "It was an affirmative command in the law, says Maimonides, to appoint "judges" and "officers" in every country and province, as it is said, Deu 16:18. "judges" they are the judges that are fixed in the sanhedrim, and such that engage in law suits come before them: "officers"; these are the masters of the rod and scourge, i.e. who beat and scourge delinquents; and these stand before the judges--and all they do, is by the order of the judges.'' Now it is one of these that is meant by "the officer"; in Munster's Hebrew Gospel, he is called who, when he had authority from the judge, could cast into prison, and that for debt; of which we have no account in the law of Moses. (g) Misn. Sanhedrim, c. 1. sect. 1. (h) T. Bab. Sanhedrim, fol. 95. 2. (i) Maimof. Hilch. Sanhedrim, c. 6. sect. 7.”
Source
1849
A.D.
1774–1849
“Agree whilst you are in the way, or wayfaring men, i.e. in this life, lest you be cast into prison, i.e. according to Sts. Cyprian, Ambrose, and Origen, into purgatory; according to St. Augustine, into hell, in which, as the debt is to be paid to inflexible justice, it can never be acquitted, and of course no release can be hoped for from that prison. (Haydock)”
Source
1871
A.D.
1871
“Agree with thine adversary--thine opponent in a matter cognizable by law. quickly, whiles thou art in the way with him--"to the magistrate," as in Luk 12:58. lest at any time--here, rather, "lest at all," or simply "lest." the adversary deliver thee to the judge, and the judge--having pronounced thee in the wrong. deliver thee to the officer--the official whose business it is to see the sentence carried into effect.”
Source

Undated

date unknown
date
unknown
“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.”
Source
“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.”
Modern · 1953 →

The in-app commentary runs from the Fathers to the early-modern record, then stops — that's where the public-domain sources end, not where the reading does. For the modern reading, follow the sources directly.