WERE THERE TWO IMPRISONMENTS OF PAUL, OR JUST ONE?
by Shawn Brasseaux
At the end of the Apostle Paul’s ministry, was he imprisoned once or twice? (We are well aware that he was in prison for two years in Caesarea [Acts 24:23-27]. This incarceration does not concern us in this study. We are interested in what happened to him at the close of the Book of Acts onward.)
Paul’s group, traveling by ship, arrived in Rome in Acts 28:16. Remember, he was a prisoner, having been arrested back in Acts 21:33 in Jerusalem. Luke closes the Book by reporting in chapter 28: “ And Paul dwelt two whole years in his own hired house, and received all that came in unto him,  Preaching the kingdom of God, and teaching those things which concern the Lord Jesus Christ, with all confidence, no man forbidding him.” This was Paul’s “house arrest” period. It was during this two-year timeframe that he penned the Epistles of Ephesians (3:1; 4:1; 6:20), Philippians (1:7,13,16), Colossians (4:3), and Philemon (verses 1 and 9). (Galatians, 1 & 2 Thessalonians, 1 & 2 Corinthians, and Romans had already been written during Acts.) Was Paul released from this house arrest? Some say yes; others say no. Let me show you verses that led me to a definite conclusion.
While under the house arrest of Acts 28:30-31, Paul wrote in Philippians 2:23-24 of Timothy: “ Him therefore I hope to send presently, so soon as I shall see how it will go with me.  But I trust in the Lord that I also myself shall come shortly.” Paul said he expected to leave Rome very soon, and he purposed to meet the saints at Philippi. Philemon 22, written around the same time, says: “But withal prepare me also a lodging: for I trust that through your prayers I shall be given unto you.” Paul expected to travel to Colosse and stay at Philemon’s home. Surely, he concluded, he would be released from his house arrest in Rome.
In 1 Timothy 1:1-3, something changes. He writes as though he is now a free man: “ Paul, an apostle of Jesus Christ by the commandment of God our Saviour, and Lord Jesus Christ, which is our hope;  Unto Timothy, my own son in the faith: Grace, mercy, and peace, from God our Father and Jesus Christ our Lord.  As I besought thee to abide still at Ephesus, when I went into Macedonia, that thou mightest charge some that they teach no other doctrine,….” He intended to travel into Macedonia, and he asked Timothy to stay at Ephesus to correct erroneous teaching. This was evidently something that occurred after Acts—after the two years of Acts 28:30-31. Paul was released (as he expected).
Titus 3:12-13 was penned contemporaneously: “ When I shall send Artemas unto thee, or Tychicus, be diligent to come unto me to Nicopolis: for I have determined there to winter.  Bring Zenas the lawyer and Apollos on their journey diligently, that nothing be wanting unto them.” Paul was not in Rome here, but in Nicopolis (modern northern Greece)—where he wanted to spend winter. He is not in prison here, but free to travel as he pleases. Surely, he was released from his first imprisonment.
By the time of 2 Timothy, nevertheless, Paul has been arrested and is incarcerated again. This is not merely house arrest as before. Now, he is in a dungeon… awaiting his certain execution. Chapter 2 says: “ Remember that Jesus Christ of the seed of David was raised from the dead according to my gospel:  Wherein I suffer trouble, as an evil doer, even unto bonds; but the word of God is not bound.” Chapter 4 continues: “ For I am now ready to be offered, and the time of my departure is at hand.  I have fought a good fight, I have finished my course, I have kept the faith:  Henceforth there is laid up for me a crown of righteousness, which the Lord, the righteous judge, shall give me at that day: and not to me only, but unto all them also that love his appearing.”
Second Timothy, in my view, is the final proof that Paul was indeed imprisoned twice at the end of his ministry. The antepenultimate verse the Holy Spirit caused him to write is as follows: “Erastus abode at Corinth: but Trophimus have I left at Miletum sick” (2 Timothy 4:20). Using a little common sense, the only way Paul could have “left” a man at Miletum is if Paul himself had been at Miletum. He would have thus been free from the Roman house arrest of Acts 28:30-31.
By the way, Second Timothy 1:16-18 is a very touching snippet of the Apostle’s joyous heart in that Roman prison: “ The Lord give mercy unto the house of Onesiphorus; for he oft refreshed me, and was not ashamed of my chain:  But, when he was in Rome, he sought me out very diligently, and found me.  The Lord grant unto him that he may find mercy of the Lord in that day: and in how many things he ministered unto me at Ephesus, thou knowest very well.”
While under the two-year house arrest in Rome (Acts 28:30-31), Paul wrote Ephesians, Philippians, Colossians, and Philemon. According to Philippians 2:24 and Philemon 22, he expected a release. First Timothy 1:3, Titus 3:12-13, and 2 Timothy 4:20 all indicate he was freed and ministered in various regions—Ephesus, Macedonia, Miletum, et cetera. Finally, he was re-arrested, re-imprisoned in Rome, and executed. Second Timothy would have been written in a dungeon, worse conditions than Acts 28:30-31, just before his death by beheading (2 Timothy 4:6-8).
The only way to reconcile all these passages is to have two imprisonments of Paul. One captivity was Acts 28:30-31 (Ephesians, Philippians, Colossians, Philemon), followed by an interlude of liberty to travel (1 Timothy, Titus), with a second imprisonment a few years later (2 Timothy).