Timothy after Rome
Anyone who has tried to piece together the life and movements of the apostle Paul after Acts 28 will tell you that it is difficult, and relies a lot on hints and a few guesses, since there is no detailed account of what he did after the events recorded in Acts. Trying to figure out Timothy’s movements carries with it the same problems. However, there are some things we can know.
Prior to Paul’s release from prison, he was making plans to visit specific people and places. One of those was Philippi. To the Philippians, he said:
I trust in the Lord Jesus to send Timothy to you shortly, that I also may be of good comfort when I know your state. For I have no man likeminded, who will naturally care for your state. For all seek their own, not the things which are Jesus Christ’s. But you know the proof of him, that as a son with the father, he has served with me in the gospel. Therefore, I hope to send him presently, as soon as I shall see how it will go with me. Bit I trust in the Lord that I also myself shall come shortly (Philippians 2:19-24).
Paul sent Epaphroditus back to Philippi with this letter, but planned on sending Timothy so that he could get a report on how the Christians in that city were doing. But Paul was waiting until he knew how things were going to go in his upcoming trial before Caesar before sending Timothy, probably because he wanted to be able to send that information as well—they being the main conduits from which support came during his imprisonment.
The book of Hebrews appears to have been written from Rome,* and the writer (Paul)* anxiously awaits the arrival of Timothy so that he can leave and visit the Christians to whom he was writing. It seems, then, as though Paul sent Timothy off on a mission (perhaps to Philippi in Macedonia), and was waiting on his return so they could go travel together again.
The two friends and fellow-soldiers of the cross went to Asia Minor, stopping at Ephesus, where they were able to reunite with the Christians they loved dearly and hadn’t seen for several years. While they were there, Paul (and perhaps Timothy as well) probably traveled to Laodicea to visit Philemon,* who he had told to “prepare me a lodging, for I trust that through your prayers I shall be released to you” (Philemon 22). Returning to Ephesus, Paul saw work that needed to be done in the congregation, but he also felt a very pressing desire to get to Macedonia personally and reunite with the ones who supported him tirelessly and out of their poverty. Thus, he told Timothy that they must separate. Timothy remained behind in Ephesus while Paul went on to Macedonia,* but he planned on returning at some point in the future.*
Timothy’s time in Ephesus was not the most pleasant of events. There were men who were completely unqualified who sought to join the eldership.* There were false teachers on the rise.* There were women who wanted to be teachers in the assembly.* Paul knew about these problems, but he was confident that Timothy would be able to handle them.
Paul most likely returned to see Timothy in Ephesus before leaving for more mission work, some believe westward to Spain. After some time, Paul made it back to Troas, but was arrested and taken back to Rome. Timothy has remained in Ephesus during this time, working with the congregation there, but then he receives a letter (2 Timothy) which causes him much concern. The Roman Empire has declared Christianity to be their enemy, and an Empire-wide persecution has begun. Paul, being perhaps the most well-known of the Christians, would have been one of their primary targets. Timothy reads the letter, which urges him to remain strong, to prepare people to continue to propagate the message of the gospel, and to endure hardships like a good soldier.* Paul is telling Timothy that they may never see each other again on this side of death.* So Timothy hurriedly gathers what things he needs and travels north to Troas to gather Paul’s books, parchments, and cloak,* and travels to Rome with John Mark (who had apparently come to Ephesus), probably by ship.
Whether he made it to Rome in time to see Paul prior to his execution, we have no way of knowing.
 *The writer, who has traditionally been identified as Paul, tells his readers “they of Italy salute you” (Hebrews 12:24).
 *It is the belief of this author that Paul is the writer of the book of Hebrews. However, as this work is not focused on that book, nor is the point here being made one of major significance, the evidence for such a conclusion does not need to be presented here.
 *Most scholars place Philemon in Colossae, but this author believes the evidence points to the nearby city of Laodicea. See the introduction and appendix of The Prodigal Slave: A Study of the Letter to Philemon by this author for more details.
 *1 Timothy 1:3.
 *1 Timothy 4:13.
 *1 Timothy 5:21-22, 24-25.
 *1 Timothy 4:1-5.
 *1 Timothy 2:9-15.
 *2 Timothy 2.
 *2 Timothy 4:6-8.
 *2 Timothy 4:9, 13