The interpretation timeline
1 Corinthians 9:22 Douay-Rheims

To the weak I became weak, that I might gain the weak. I became all things to all men, that I might save all.

A.D. 215 – 1871 11 witnesses 13 excerpts

Patristic

before A.D. 750
215
A.D.
c. A.D. 150–215
“For we are taught what is like by what is like. For says Solomon, "Answer a fool according to his folly." Wherefore also, to those that ask the wisdom that is with us, we are to hold out things suitable, that with the greatest possible ease they may, through their own ideas, be likely to arrive at faith in the truth. For "I became all things to all men, that I might gain all men." Since also "the rain" of the divine grace is sent down "on the just and the unjust." "Is He the God of the Jews only, and not also of the Gentiles? Yes, also of the Gentiles: if indeed He is one God," exclaims the noble apostle.”
Source
220
A.D.
Tertullian Patristic
c. A.D. 150–220
“" No doubt he used to please them by celebrating the Saturnalia and New-year's day! [Was it so] or was it by moderation and patience? by gravity, by kindness, by integrity? In like manner, when he is saying, "I have become all things to all, that I may gain all," does he mean "to idolaters an idolater? ""to heathens a heathen? ""to the worldly worldly? "But albeit he does not prohibit us from having our conversation with idolaters and adulterers, and the other criminals, saying, "Otherwise ye would go out from the world," of course he does not so slacken those reins of conversation that, since it is necessary for us both to live and to mingle with sinners, we may be able to sin with them too.”
Source
“They seemed to be changing their company from respect of persons. And yet as Paul himself "became all things to all men," that he might gain all, it was possible that Peter also might have betaken himself to the same plan of practising somewhat different from what he taught.”
“But so did circumstances require him to "become all things to all, in order to gain all; " "travailing in birth with them until Christ should be formed in them; " and "cherishing, as it were a nurse," the little ones of faith, by teaching them some things "by way of indulgence, not by way of command"-for it is one thing to indulge, another to bid-permitting a temporary licence of re-marriage on account of the "weakness of the flesh," just as Moses of divorcing on account of "the hardness of the heart.”
Source
258
A.D.
Cyprian Patristic
c. A.D. 200–258
“If we reject the repentance of those who have some confidence in a conscience that may be tolerated; at once with their wife, with their children, whom they had kept safe, they are hurried by the devil's invitation into heresy or schism; and it will be attributed to us in the day of judgment, that we have not cared for the wounded sheep, and that on account of a single wounded one we have lost many sound ones. And whereas the Lord left the ninety and nine that were whole, and sought after the one wandering and weary, and Himself carried it, when found, upon His shoulders, we not only do not seek the lapsed, but even drive them away when they come to us; and while false prophets are not ceasing to lay waste and tear Christ's flock, we give an opportunity to dogs and wolves, so that those whom a hateful persecution has not destroyed, we ruin by our hardness and inhumanity. And what will become, dearest brother, of what the apostle says: "I please all men in all things, not seeking mine own profit, but the profit of many, that they may be saved. Be ye followers of me, as I also am of Christ." And again: "To the weak I became as weak, that I might gain the weak." And again: "Whether one member suffer, all the members suffer with it; or one member rejoice, all the members rejoice with it."”
Source
386
A.D.
Cyril of Jerusalem Patristic
A.D. 313–386
“Everywhere the Savior becomes "all things to all men." To the hungry, bread; to the thirsty, water; to the dead, resurrection; to the sick, a physician; to sinners, redemption.”
407
A.D.
John Chrysostom Patristic
A.D. 347–407
“"To the weak became I weak, that I might gain the weak:" in this part coming to their case, with a view to which also all these things have been spoken. However, those were much greater things, but this more to the purpose; whence also he hath placed it after them. Indeed he did the same thing likewise in his Epistle to the Romans, when he was finding fault about meats; and so in many other places. Next, not to waste time by naming all severally, he saith, "I am become all things to all men, that I may by all means save some." Seest thou how far it is carried? "I am become all things to all men," not expecting, however, to save all, but that I may save though it be but a few. And so great care and service have I undergone, as one naturally would who was about saving all, far however from hoping to gain all: which was truly magnanimous and a proof of burning zeal. Since likewise the sower sowed every where, and saved not all the seed, notwithstanding he did his part. And having mentioned the fewness of those who are saved, again, adding, "by all means," he consoled those to whom this was a grief. For though it be not possible that all the seed should be saved, nevertheless it cannot be that all should perish. Wherefore he said, "by all means," because one so ardently zealous must certainly have some success.”
Source
430
A.D.
Augustine of Hippo Patristic
A.D. 354–430
“This is correctly interpreted to mean that he, not by lying but by sympathy, brought it about that he enabled their con-version by his own great love which made it seem as though he himself were afflicted with that evil of which he wished to heal them.”
523
A.D.
c. A.D. 450–523
“Craftiness in the soul is like a harlot in the street; for as the harlot speaketh with all men and putteth on all persons so that she may appear to be like unto every man, even so doth craftiness appear in every variety of opinion, and it prepareth the various kinds of ornamented forms which are required of it, that it may show itself to be like unto every man by them. And that which was written by the Apostle in integrity, "I have become all things unto all men, that I might profit all men", is wrought in the opposite manner by craftiness, which becometh all things unto all men that it may destroy all men, and that it may mock and laugh at all men.”
Source

Scholastic

c. 1100 – 1500
1270
A.D.
1225–1276
“Above he showed that he does not wish to accept expenses, and this on account of the intention of a reward; here he shows that he did the same thing on account of love of the Gospel. Where first he says that he made himself the servant of all; second, that he strove to accommodate himself to all, there "and I became to the Jews," etc.; third, he subjoins the reason why he did this, there "but all things I do on account of the Gospel," etc. In the first he implies a threefold commendable condition in servitude: which are generality, liberality, usefulness. He serves therefore freely or liberally, there "when I was free," etc.; generally, there "of all... me," etc.; usefully, there "that I might gain the more," etc. He says therefore "for when I was," etc., as if to say: I will set forth the Gospel without expense, for I have done even more, namely that although "I was free from all," etc., that is, obligated by no one's merits, "I made myself the servant of all," accommodating myself to all through lowliness, and as it were constituting myself a debtor — 2 Cor. 4:5: "but we are your servants through Jesus." And this "that I might gain the more," that is, that I might make a gain of my preaching and servitude. For he sought not things, but souls — 2 Cor. 12:14: "I seek not your things, but you." For if it is commendable to serve in temporal things for temporal gain, how much more in spiritual things for spiritual gain? Then, when he says "and I became to the Jews," etc., here he shows that he strove to accommodate himself to all. And first he says that he accommodated himself to those not yet converted; second, that also to those already converted, there "I became to the weak," etc.; third, that generally to all, there "I became all things to all," etc. In the first he first says that he accommodated himself to the Jews; second, that to the Samaritans, there "and to those who are under the law," etc.; third, that to the Gentiles, there "to those who were without the law," etc. In the first, he first touches the accommodation; second, the reason for the accommodation, there "that the Jews," etc. He says therefore: "and I became to the Jews as a Jew," namely by observing certain legal things, as in the distinction of foods, in the circumcision of Timothy, Acts 16:3, in the legal purification, Acts 21:24. But this can be understood in two ways. In one way, according to Jerome, "I became to the Jews as a Jew" through a dispensation of simulation — for he pretended to observe certain legal things, which nevertheless he did not observe. In another way, according to Augustine, "I became a Jew," etc. — for he truly condescended to them in the observance of certain legal things on account of pious compassion; and he did this that he might gain the Jews for Christ, that is, that he might convert them to the faith of Christ. Then, when he says "and to those who are under the law," etc., here he says that he was accommodating himself to the Samaritans. Where three things are noted about him: first, his sagacity in that he accommodated himself; second, his freedom in that he was not under the law; third, his usefulness in that he was gaining them. He says therefore: "I am also to those who are under the law of Moses," that is, to the Samaritans, who are not Jews but Assyrians, who were brought to inhabit the land of Israel, 4 Kings 17:24 ff. These also were under the law of Moses, because they received only the five books of Moses. To these therefore "I became as if I were under the law," namely by approving the law, and by teaching Christ from it, although "I myself was not under the law," according to literal observance, or servilely, because "the law is not laid down for the just man," 1 Tim. 1:9. And I did this therefore "that I might gain those who were under the law," namely the Samaritans themselves, by converting them to the faith of Christ. Then, when he says "to those who were without the law," etc., here he says that he accommodated himself to the Gentiles. Where first he touches his conformity; second, the truth of his faith, there "although without the law," etc.; third, the rectitude of his intention, there "that I might gain," etc. And this is: "and I became to those who were without the law," that is, to the Gentiles — Rom. 2:14: "for the Gentiles, who do not have the law" — "as if I were without law," that is, by assenting to their reasonings, and to the good positions of the philosophers, as is clear in Acts 17; "although I was not without law" — Rom. 7:25: "with the mind I serve the law of God" — "but I was in the law," not the Jewish law, but of Christ, who is God, and not Moses. Concerning which, Gal. 6:2: "bear one another's burdens, and thus you will fulfill," etc. And I did this therefore "that I might gain those who were without the law," by converting the Gentiles to the faith. O happy zealot! Gregory: "there is no sacrifice like the zeal of souls." Then, when he says "I became to the weak," etc., here he shows that he accommodated himself to those already converted. Where first he sets forth the good manner, second the due end, there "that the weak." He says therefore: "I became also to the weak," in faith, "weak," by abstaining from lawful things — 2 Cor. 11:29: "who is weak, and I am not weak?" So does the good physician, who eats the food of the sick man, that he may provoke him to eat, and so heal him. And this I did "that I might gain the weak," strengthening them in the faith. And briefly, "I became all things to all," as if I were of every sect. Therefore it is said below, 10:33: "as I also please all in all things." And this "that I might make all safe." In the ankle-length vestment which Aaron had, the whole world was depicted, Wisdom 18:24. And, 4 Kings 4:34, Elisha contracted himself to the manner of the boy, and thus revived him. And because, according to Boethius, every otherness is discordant, but likeness truly is to be sought, therefore spiritual men, saving the observance of their life and religion, ought to conform themselves to all. Then, when he says "all things I do on account of the Gospel," above he showed that he strove to accommodate himself to all; here he subjoins the reason why he does this, and this is twofold: one on the part of the Gospel, namely that it may have a free course; the other on his own part, namely that he may obtain the promised reward, there "that a partaker," etc. And this is what he says: "but all things I do on account of the Gospel," to be preached without impediment, "that I may become a partaker of it," that is, of the promises which are contained in it — Matt. 5:19: "whoever shall do and teach, he shall be called great in the kingdom of heaven."”

Post-Reformation

c. 1650 – 1900
1771
A.D.
John Gill Reformed
1697–1771
“And this I do for the Gospel's sake,.... The Alexandrian copy and some others read, "all things I do", &c. and so the Vulgate Latin and Ethiopic versions; that is, he became all things to all men, and so and so to different persons; not for his own sake, for his own temporal advantage, or to curry favour with men; not for the sake of gaining wealth, or honour and applause to himself, but for the spread of the Gospel, and its greater usefulness among men: to which he adds, that I might be partaker thereof with you; meaning either the fruit of the Gospel, the conversion and salvation of sinners, which would be matter of joy both to him and them; or the blessings of grace and eternal life, which the Gospel reveals and promises, which he desired to enjoy in common with others, not only with the Corinthians, for the word "you" is not in the original text, but with Jews and Gentiles; with men of all sorts, who may be gained over to Christ, and saved by him, through the ministry of the word.”
Source
1832
A.D.
Adam Clarke Methodist
1762–1832
“To the weak became I as weak - Those who were conscientiously scrupulous, even in respect to lawful things. I am made all things to all men - I assumed every shape and form consistent with innocency and perfect integrity; giving up my own will, my own way, my own ease, my own pleasure, and my own profit, that I might save the souls of all. Let those who plead for the system of accommodation on the example of St. Paul, attend to the end he had in view, and the manner in which he pursued that end. It was not to get money, influence, or honor, but to save Souls! It was not to get ease but to increase his labors. It was not to save his life, but rather that it should be a sacrifice for the good of immortal souls! A parallel saying to this of St. Paul has been quoted from Achilles Tatius, lib. v., cap. xix., where Clitophon says, on having received a letter from Leucippe: Τουτοις εντυχων παντα εγινομην ὁμου, ανεφλεγομην, ωχριων, εθαυμαζον, ηπιστουν, εχαιρον, ηχθομην· "When I read the contents, I became all things at once; I was inflamed, I grew pale, I was struck with wonder; I doubted, I rejoiced, became sad." The same form of speech is frequent among Greek writers. I think this casts some light on the apostle's meaning. That I might by all means save some - On this clause there are some very important readings found in the MSS. and versions. Instead of παντως τινας σωσω, that I might by all means save some; παντας σωσω, that I might save all, is the reading of DEFG, Syriac, Vulgate, Ethiopic, all the Itala, and several of the fathers. This reading Bishop Pearce prefers, because it is more agreeable to St. Paul's meaning here, and exactly agrees with what he says, Co1 10:33, and makes his design more extensive and noble. Wakefield also prefers this reading.”
Source
1871
A.D.
1871
“gain the weak--that is, establish, instead of being a stumbling-block to inexperienced Christians (Co1 8:7) Rom 14:1, "Weak in the faith." ALFORD thinks the "weak" are not Christians at all, for these have been already "won"; but those outside the Church, who are yet "without strength" to believe (Rom 5:6). But when "weak" Christians are by the condescending love of stronger brethren kept from falling from faith, they are well said to be "gained" or won. by all means . . . some--The gain of even "some" is worth the expenditure of "all means." He conformed himself to the feelings of each in the several classes, that out of them all he might gain some.”
Source
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.