Paul founded the Corinthian church on his second missionary journey as described in Acts 18, after arriving there from Athens, where the soils for spiritual growth were evidently quite sterile because of its many philosophies and the propensity of people there to “spend their time in nothing other than telling or hearing something new” (Acts 17:21, how very like America!). He had come to Athens having been driven out of Philippi, then Thessalonica, and then Berea, but left Silas and Timothy there in Macedonia to more firmly establish the churches before joining him in Athens.
Now those who conducted Paul brought him as far as Athens; and receiving a command for Silas and Timothy to come to him as soon as possible, they departed.
Timothy evidently did join Paul in Athens, but Paul was so concerned about the new believers in Thessalonica and the persecutions from the Jews there that he sent Timothy back to Macedonia to look after their welfare:
Therefore when we could endure it no longer, we thought it best to be left behind at Athens alone; and we sent Timothy, our brother and God’s fellow worker in the gospel of Christ, to strengthen and encourage you as to your faith, so that no man may be disturbed by these afflictions; for you yourselves know that we have been destined for this.
1 Thessalonians 3:1-3
Though not entirely clear, it would seem that Paul also sent Silas back to Macedonia with Timothy, perhaps to Philippi. For Luke records that while in Corinth “Silas and Timothy came down from Macedonia” (Acts 18:5), and Paul himself writes to the Philippians “that at the first preaching of the gospel, after I departed from Macedonia, no church shared with me in the matter of giving and receiving but you alone” (Philippians 4:15). Luke also notes that when Silas and Timothy came down from Macedonia, “Paul began devoting himself completely to the word, solemnly testifying to the Jews that Jesus was the Christ” (Acts 18:5), while Paul writes to the Corinthians that “when I was present with you and was in need, I was not a burden to anyone; for when the brethren came from Macedonia, they fully supplied my need, and in everything I kept myself from being a burden to you” (2 Cor 11:9). How exactly they supplied Paul’s needs may have included their own labors, but as Paul’s words make clear, it must also have included the support of the Philippians, perhaps by the agency of Silas.
It is clear that when Timothy returned from visiting the Thessalonians Silas was with him and Paul had by then moved on to Corinth (Acts 18:5). Timothy’s report was good, that the Thessalonians were standing firm against the persecution of the Jews that had driven Paul out. However, they had questions and issues that needed addressed by the apostle, and it was from Corinth where “he settled there a year and six months” (Acts 18:11) that Paul wrote both 1 and 2 Thessalonians to address these issues and encourage them in their faith.
While in Corinth Paul was again persecuted by the Jews, who brought him before the judgment seat of Gallio, but Gallio refused to hear their case (Acts 18:12-16). After this event he “remained many days longer” but eventually “put out to sea for Syria” along with Priscilla and Aquila (Acts 18:18). On the way, though, he made a brief stop in Ephesus, an important city being the capital of the Roman province of Asia, and perhaps testing the spiritual waters “entered the synagogue and reasoned with the Jews” (Acts 18:19). Surprisingly (considering the persecution he had met with from the Jews in almost every other place) “they asked him to stay for a longer time”. However, “he did not consent” (Acts 18:20), but leaving Priscilla and Aquila there and promising to return according to the will of the Lord (Acts 18:19:21), he continued on to Syria. Landing in Caesarea, he went up to visit the church (likely meaning the church in Jerusalem) and finally returned to Antioch, thus ending his second missionary journey (Acts 18:22). After a short stay he set out by land on his third missionary journey, strengthening the churches in Galatia (Acts 18:23) and then returning to Ephesus where he would spend 3 years (Acts 20:31) in a most effectual ministry that would bear much fruit (see 1 Cor 16:9).
Towards the end of this stay in Ephesus Paul received a report from “Chloe’s people” (1 Cor 1:11-12) of some divisions in the church that had developed. For some there in Corinth were throwing their allegiance to Paul, some to Peter, and some to Apollos who was an eloquent man and “mighty in the Scriptures” (Acts 18:24), whom Priscilla and Aquila had sent to them from Ephesus prior to Paul’s coming (Acts 18:27-28). In response to this report and other questions he had received from the Corinthians Paul wrote 1 Corinthians. Prior to this he had in some manner communicated to them that he planned on coming to them, probably by ship across the Aegean from Ephesus, and from there to travel into Macedonia and then back again to Corinth.
And in this confidence I intended at first to come to you, that you might twice receive a blessing; that is, to pass your way into Macedonia, and again from Macedonia to come to you, and by you to be helped on my journey to Judea.
2 Corinthians 1:15-16
But as it turned out, his plans changed as he communicated towards the end of what we know as 1 Corinthians:
But I shall come to you after I go through Macedonia, for I am going through Macedonia; and perhaps I shall stay with you, or even spend the winter, that you may send me on my way wherever I may go. For I do not wish to see you now just in passing (due to the issues that had arisen there in Corinth that he would need time to deal with); for I hope to remain with you for some time, if the Lord permits. But I shall remain in Ephesus until Pentecost; for a wide door for effective service has opened to me, and there are many adversaries.
1 Corinthians 16:5-9
They evidently took offense at this, for Paul was forced to defend himself to them in the verses following those above about his original plans:
Therefore, I was not vacillating when I intended to do this, was I? Or that which I purpose, do I purpose according to the flesh, that with me there should be yes, yes and no, no at the same time? But as God is faithful, our word to you is not yes and no….But I call God as witness to my soul, that to spare you I came no more to Corinth…
2 Corinthians 1:17-18,23
In the Acts chronology, 1 Corinthians would have been written by Paul precisely between Acts 19:22 and 19:23, after Paul had sent Timothy and Erastus into Macedonia, but before the time of the disturbance caused by Demetrius and the Ephesian craftsmen:
Now after these things were finished (the events with the seven sons of Sceva and the burning of the magic books, vss 13-20) Paul purposed in the spirit to go to Jerusalem after he had passed through Macedonia and Achaia saying, “After I have been there, I must also see Rome.” And having sent into Macedonia two of those who ministered to him, Timothy and Erastus, he himself stayed in Asia for a while. And about that time there arose no small disturbance concerning the Way…
The purpose of the Jerusalem visit was to “bring alms to my nation” (Acts 24:17), an offering Paul raised from the churches he had planted.
Now concerning the collection for the saints, as I directed the churches of Galatia, so do you also.On the first day of every week let each one of you put aside and save, as he may prosper, that no collections be made when I come.And when I arrive, whomever you may approve, I shall send them with letters to carry your gift to Jerusalem;and if it is fitting for me to go also, they will go with me.
1 Corinthians 16:1-4
But now, I am going to Jerusalem serving the saints. For Macedonia and Achaia have been pleased to make a contribution for the poor among the saints in Jerusalem. Yes, they were pleased to do so, and they are indebted to them. For if the Gentiles have shared in their spiritual things, they are indebted to minister to them also in material things.
This offering would have the effect of promoting peace between Jew and Gentile by making the new Gentile converts more acceptable to the Jewish believers—many of whom still felt it necessary for them to submit to the Jewish law. It would also provide a Christian witness to the unbelieving Jews that the God-fearing Gentiles, many of whom used to associate themselves with the Jewish synagogues (along with their tithes and offerings), had not been turned by Paul from the substance of pure and undefiled religion (cf. James 1:27).
Back to the Acts chronology, it is clear from Luke’s words in Acts 19:21 that Paul had by this time made up his mind to not sail directly across to Corinth but to travel by way of Macedonia first and then come to Corinth. He had also already sent Timothy ahead of him, along with Erastus, who was from Corinth and the city treasurer:
Gaius, host to me and to the whole church, greets you. Erastus, the city treasurer greets you, and Quartus, the brother. (Note: The book or Romans was written from Corinth.)
Erastus remained at Corinth…
2 Timothy 4:20
Paul’s purpose for sending Timothy and Erastus was to prepare for his coming, especially in regard to the offering which he was taking up for the saints in Judea (see his additional exhortation to this effect in 2 Corinthians 8 and 9). Paul mentions having already sent Timothy in 1 Corinthians, but it is clear that Timothy was not the bearer of that letter, and that it was uncertain when Timothy would arrive. This makes sense in light of Luke’s record that Timothy went first into Macedonia.
For this reason I have sent to you Timothy, who is my beloved and faithful child in the Lord, and he will remind you of my ways which are in Christ, just as I teach everywhere in every church.
1 Corinthians 4:17
Now if (or when/whenever; see 1 Jn 2:28, 3:2 for similar usage of the Greek ἐάν, cf. also John 12:32 and 14:3 for how this conditional particle can be used to denote the certainty of an event even when its timing is unknown) Timothy comes, see that he is with you without cause to be afraid; for he is doing the Lord’s work, as I also am. Let no one therefore despise him. But send him on his way in peace, so that he may come to me; for I expect him with the brethren.
1 Corinthians 16:10-11
As Paul was himself soon heading to Macedonia by way of Troas it was along this path that he expected to receive Timothy back. Thus, after accompanying Erastus to Corinth to look into the issues that had arisen there, as well as to encourage them in regard to the offering Paul was taking up for the Judean saints, Timothy was to head north again “with the brethren” (cf. 1 Cor 16:12) to rejoin the apostle wherever the timing of their travels would allow them to meet, perhaps even returning all the way to Troas. Likely included among these brethren was Titus, who it appears had some closer relationship to the Corinthians than Timothy, and had perhaps been there for some longer time ministering to them on Paul’s behalf (cf. 2 Cor 2:13, 7:6,13,14, 8:6,16,23, 12:18, and contrast 1 Cor 16:10-11). It was perhaps even Titus whom Paul sent with 1 Corinthians, and who would be most able to report back to him about its reception and effect upon them. However, not finding Titus in Troas, which Paul evidently thought likely given the time that had elapsed, He went on to Macedonia eagerly seeking and concerned about what news Titus and Timothy might bring in regard to the Corinthians, and this in spite of a door of opportunity that had opened for the gospel:
Now when I came to Troas for the gospel of Christ and when a door was opened for me in the Lord, I had no rest for my spirit, not finding Titus my brother; but taking my leave of them, I went on to Macedonia.
2 Corinthians 2:12-13
Thus moving on from Troas Paul came to Macedonia, where he met up with both Timothy and Titus, who brought good news that greatly comforted the apostle in his concern for them, that the letter he had written had produced its desired effect of a sincere repentance among the Corinthians:
For even when we came into Macedonia our flesh had no rest, but we were afflicted on every side: conflicts without, fears within. But God, who comforts the depressed, comforted us by the coming of Titus; and not only by his coming, but also by the comfort with which he was comforted in you, as he reported to us your longing, your mourning, your zeal for me; so that I rejoiced even more. For though I caused you sorrow by my letter, I do not regret it; though I did regret it—for I see that that letter caused you sorrow, though only for a while—I now rejoice, not that you were made sorrowful, but that you were made sorrowful to the point of repentance; for you were made sorrowful according to the will of God, in order that you might not suffer loss in anything through us. For the sorrow that is according to the will of God produces a repentance without regret, leading to salvation; but the sorrow of the world produces death. For behold what earnestness this very thing, this godly sorrow, has produced in you: what vindication of yourselves, what indignation, what fear, what longing, what zeal, what avenging of wrong! In everything you demonstrated yourselves to be innocent in the matter. So although I wrote to you it was not for the sake of the offender, nor for the sake of the one offended, but that your earnestness on our behalf might be made known to you in the sight of God. For this reason we have been comforted. And besides our comfort, we rejoiced even much more for the joy of Titus, because his spirit has been refreshed by you all. For if in anything I have boasted to him about you, I was not put to shame; but as we spoke all things to you in truth, so also our boasting before Titus proved to be the truth. And his affection abounds all the more toward you, as he remembers the obedience of you all, how you received him with fear and trembling. I rejoice that in everything I have confidence in you.
2 Corinthians 7:5-16
That Timothy had also rejoined the apostle in Macedonia along with Titus is clear from Paul’s greeting in his second letter to the Corinthians which was written while there in Macedonia:
Paul, an apostle of Christ Jesus by the will of God, and Timothy our brother, to the church of God which is at Corinth with all the saints who are throughout Achaia:
2 Corinthians 1:1
Thus it was at this time that Paul wrote 2 Corinthians, rejoicing in the comfort Titus had brought, while at the same time preparing them for his much awaited visit. For he wanted them to be prepared to make good on the offering for the saints in Judea which he had already discussed with them (2 Cor 8-9). And although the news Titus brought comforted the apostle, it was clear that the crisis was by no means entirely resolved. Thus he writes:
Now I, Paul, myself urge you by the meekness and gentleness of Christ—I who am meek when face to face with you, but bold toward you when absent! I ask that when I am present I may not be bold with the confidence with which I propose to be courageous against some, who regard us as if we walked according to the flesh.
2 Corinthians 10:1-2
For I am afraid that perhaps when I come I may find you to be not what I wish and may be found by you to be not what you wish; that perhaps there may be strife, jealousy, angry tempers, disputes, slanders, gossip, arrogance, disturbances; I am afraid that when I come again my God may humiliate me before you, and I may mourn over many of those who have sinned in the past and not repented of the impurity, immorality and sensuality which they have practiced. This is the third time I am coming to you. Every fact is to be confirmed by the testimony of two or three witnesses. I have previously said when present the second time, and though now absent I say in advance to those who have sinned in the past and to all the rest as well, that if I come again, I will not spare anyone.
2 Corinthians 12:20-13:2
Luke describes this visit in Acts 20:2-3.
And when he had gone through those districts and had given them much exhortation, he came to Greece. And there he spent three months, and when a plot was formed against him by the Jews as he was about to set sail for Syria, he determined to return through Macedonia.
While in Corinth during those three months Paul wrote the letter to the Romans.