Writing from his first imprisonment in Rome, Paul told the Philippians that things were going relatively well. For two full years, Paul was permitted to rent out private quarters in Rome at his own expense, while under the guard of a Roman centurion (Acts 28:30). Paul was allowed to receive visitors from the local house churches and Jewish synagogues (Acts 28:17-31). The Gospel was being spread throughout Nero Caesar’s household (“the Praetorian Guard and to everyone else”) (Phil. 1:12-13). Because of Paul’s favorable circumstances, other believers were encouraged to speak and spread the Gospel without fear (Phil. 1:13-18). Paul anticipated his imminent release from custody (Phil. 1:19; 2:24). However, unfortunately, the Great Fire of Rome (July 19, AD 64) and Nero’s official persecution of Christians (beginning November, AD 64) was just around the corner.
Paul had appealed to Nero, but there is some historical evidence to support the idea that Nero (contrary to Emperor Claudius) had delegated the actual hearing of cases to others. Paul’s case was most likely heard by the prefect of the Praetorian Guard. Further, Paul was most likely released from custody before the Great Fire of Rome and the imminent persecution of Christians by Nero, starting several months after the fire.
It should be noted that Luke’s biography (Acts) does not mention the specifics of the first trial. Quite probably, Luke’s biography (Acts) was prepared to assist in the trial before the prefect of the Praetorian Guard. Luke’s biography is notably very positive in its presentation of evidence about Paul’s interactions with representatives of Rome. On the other hand, Acts portrayed the unbelieving Jewish leadership in Jerusalem as Paul’s primary antagonists. Luke’s biography probably served its initial and intended purpose. Paul was tried and acquitted, which is consistent with Paul’s anticipation of an impending release from custody as stated in his letter to the Philippians (Phil. 1:19; 2:24). A few years later, during the ongoing Neronian persecutions of Christians, Paul was probably rearrested and thereafter, ultimately executed. Kenneth Gentry, Th.D, argues that the Neronian persecutions of Christians continued up to the death/suicide of Nero on June 9, AD 68.
It should be noted that Paul also wrote of his anticipated imminent release from custody in Rome in his letter to Philemon (Philem. 1:22). At that time, he expected to visit friends in Asia. Between his two imprisonments in Rome, Paul continued on his missionary journeys. He appears to have visited Macedonia (Phil. 2:24), Crete (Titus 1:5), Ephesus (1 Tim. 1:3), Miletus (2 Tim. 4:20), Troas (2 Tim. 4:13), and Nicopolis (in Epirus, northwestern coast of Achaia) (Tit. 3:12). At some point, Paul probably also traveled to Spain (Rom. 15: 24-28).
It appears that Paul wrote Titus and First Timothy between his two imprisonments in Rome, and he wrote Second Timothy during his second and last imprisonment in Rome. First Timothy and the letter to Titus were probably written from somewhere in Macedonia around AD 64 to AD 65. The subject matter of First Timothy and Titus are very similar. Paul’s final years before his last imprisonment focused on placing things (church affairs and warnings as to false teachings) in order before his departure to be with the Lord.
According to tradition, Paul was arrested by the order of Nero and arising out of Nero’s accusations that Christians were the cause of the Great Fire of Rome that occurred in AD 64. In his final imprisonment, Paul was treated more harshly. He was no longer treated as an accused Roman citizen. Instead, during his final imprisonment, Paul was shackled and treated as a criminal (2 Tim. 2:9). During his first imprisonment in Rome, Paul was easy to locate, and many came to meet with Paul at his rented quarters in Rome (Acts 28:16-31). In his second imprisonment, Paul was harder to locate. At 2 Timothy 1:16-17, Paul noted that Onesiphorus of Ephesus visited with Paul during his final imprisonment, but he had found it difficult to locate Paul.
Most of Paul’s friends had abandoned him or no longer supported him during the second imprisonment (2 Tim. 1:15; 4:9-11; 16-17). Only Luke remained with Paul (2 Tim. 4:11). While in his final imprisonment, Paul wrote to Timothy, “[D]o not be ashamed of the testimony of our Lord or of me his prisoner” (2 Tim. 1:8). At that point, to be associated with Paul was to risk one’s life. Apparently, during his second Roman imprisonment, there was a preliminary hearing and no one supported him (2 Tim. 4:16). Instead of his release, Paul anticipated his imminent execution (2 Tim. 4:6-8). As to his predicament and his approaching execution, Paul famously said,
I have fought the good fight, I have finished the course, I have kept the faith: in the future there is reserved for me the crown of righteousness, which the Lord, the righteous judge, will award to me on that day, and not only to me, but also to all who have loved His appearing.
(2 Tim. 4:7-8).
Around AD 66-67, according to tradition, on one particular day, Paul was escorted outside of Rome’s walls and along the Ostian Way to his place of execution. The Roman executioner then used a broad, double-bladed sword to sever Paul’s head from his body with one powerful swing of the blade. Thereafter, Paul was face to face with the Lord in Heaven, where he continues to reside until this very day (2 Cor. 5:8). Paul had confidence that the Lord would deliver Paul to the Lord’s heavenly kingdom (2 Tim. 4:18).
 Gentry, Jr., Kenneth L. The Beast of Revelation. American Vision, 2002, pp. 67-68.
 “Paul, the Apostle.” The International Standard Bible Encyclopedia: Volume Three: K-P, Gen. Editor Geoffrey W. Bromiley, et al., William B. Eerdmans Publishing Company, 1988, p. 719.
 Picirilla, Robert E. Paul the Apostle. Moody Press, Chicago, 1986, pp. 228-233.
 Picirilla, pp. 234, 238.
 Picirilli, p. 242; Gentry, p. 64.
 Picirilli, pp 230, 234, 247.