Archive for the ‘2 Timothy’ Category


2 Timothy chapter 4

June 2, 2010

Paul had urged Timothy to be faithful — to be passionately loyal, even if doing so would cost him his life. He had warned his son in the faith about the inevitable opposition, and instructed him how to address his opponents. He had warned Timothy about the moral corruption of the last days. And he had called Timothy to remain true to the scriptures.

Now Paul’s message reached its ultimate crescendo:

2Ti 4:1 In the presence of God and of Christ Jesus, who will judge the living and the dead, and in view of his appearing and his kingdom, I give you this charge:
2Ti 4:2 Preach the Word; be prepared in season and out of season; correct, rebuke and encourage–with great patience and careful instruction.
2Ti 4:3 For the time will come when men will not put up with sound doctrine. Instead, to suit their own desires, they will gather around them a great number of teachers to say what their itching ears want to hear.
2Ti 4:4 They will turn their ears away from the truth and turn aside to myths.
2Ti 4:5 But you, keep your head in all situations, endure hardship, do the work of an evangelist, discharge all the duties of your ministry.

Paul based his plea on the most profound truths imaginable. He delivered the plea in the presence of the Father and the Son — the very ones who gave the message to Paul; the ones in whose hands we will all face judgment; and the ones from whom we hope to receive an eternal reward. How Timothy responded to this divine appeal would not be without consequences, either for good or bad. Timothy would do well to pay close attention, and to carry out everything Paul was about to say.

Preach the Word! In three words, that is the mission. He must not let anything interfere with that mission — not church administration, not his personal life, nor any other matters. If he fulfilled that mission, he would receive “Well done!” from his master. If he had not, then nothing else he did would make up for the failure.

Sometimes it would be easy to preach the word. And sometimes not. Some people would long to hear the message, and some would be infuriated by it. He must be equally urgent to deliver the full, clear message in either case. He must do so patiently, not giving up on the slow of heart. And he must do so carefully — accurately and thoroughly.

As Paul had done throughout the letter, he contrasted what Timothy must do with what others would do. People would turn aside from the pure message, preferring a less demanding standard. They would shrink from hardship, and would leave out the more difficult parts. Timothy must be different!

Again, Paul reminded Timothy of his own example. Paul was not shrinking back from paying the ultimate price. He did so because of the reward that was promised. Timothy, too, could have that reward, presented by God himself.

Paul also reminded Timothy of the unfaithful brothers who had deserted at the onset of Nero’s persecution. And he called on Timothy to be brave and to come to visit him in prison. He requested some personal effects, perhaps items that were left behind when Paul was taken prisoner. One can only wonder whether there was no one remaining in Rome who was willing to bring Paul a coat in prison.

In conclusion, Paul remembered his personal relationships and sent greetings — the last recorded words we have from the great apostle.

The message of 2 Timothy is faithfulness — a passionate loyalty that overcomes any obstacle. Do we have that kind of faithfulness?

Rev 2:10 Do not be afraid of what you are about to suffer. I tell you, the devil will put some of you in prison to test you, and you will suffer persecution for ten days. Be faithful, even to the point of death, and I will give you the crown of life.
Rev 2:11 He who has an ear, let him hear what the Spirit says to the churches. He who overcomes will not be hurt at all by the second death.


2 Timothy: Chapter 3

May 23, 2010

Christian life was becoming harder than ever. The ever-present opposition from Satan was taking on a new and frightening dimension as Roman persecution increased. Christians were dying for their faith. And some were renouncing their faith to save their own skin. Christian leaders in particular were feeling a pressure to back off of certain teachings and to take a lower profile. As Paul continued into chapter three of the letter, he drew the lines of battle in plain, unmistakable terms:

2Ti 3:1 But mark this: There will be terrible times in the last days.
2Ti 3:2 People will be lovers of themselves, lovers of money, boastful, proud, abusive, disobedient to their parents, ungrateful, unholy,
2Ti 3:3 without love, unforgiving, slanderous, without self-control, brutal, not lovers of the good,
2Ti 3:4 treacherous, rash, conceited, lovers of pleasure rather than lovers of God—
2Ti 3:5 having a form of godliness but denying its power. Have nothing to do with them.

What made these last days terrible was not primarily Roman persecution. Rather, it was the sinful hearts of many, even some who sought to have a “form of godliness.” People loved the wrong things. Persecution simply reveals what we love most.

2Ti 3:6 They are the kind who worm their way into homes and gain control over weak-willed women, who are loaded down with sins and are swayed by all kinds of evil desires,
2Ti 3:7 always learning but never able to acknowledge the truth.
2Ti 3:8 Just as Jannes and Jambres opposed Moses, so also these men oppose the truth—men of depraved minds, who, as far as the faith is concerned, are rejected.
2Ti 3:9 But they will not get very far because, as in the case of those men, their folly will be clear to everyone.

Some leaders, taking advantage of the carnal Christians, led them astray with a weaker, watered-down version of the message. They gained control over the weak-willed, over those who were susceptible to temptation through their evil desires. That kind of message was more attractive to the weak in those treacherous times. They were weak, not because they had not heard the truth (they were always learning). But it seems that the unfaithful Christians had not experienced the whole truth, because they had not put the truth into practice.

Joh 8:31 To the Jews who had believed him, Jesus said, “If you hold to my teaching, you are really my disciples.
Joh 8:32 Then you will know the truth, and the truth will set you free.”

But in the end, just as Pharaoh’s magicians ultimately failed to prevail against God, the leaders who were leading these people astray would also fail. They had no power, and could not possibly prevail against God. They would do much harm, and would lead many astray, but eventually they would be seen to be false teachers and enemies of God.

2Ti 3:10 You, however, know all about my teaching, my way of life, my purpose, faith, patience, love, endurance,
2Ti 3:11 persecutions, sufferings—what kinds of things happened to me in Antioch, Iconium and Lystra, the persecutions I endured. Yet the Lord rescued me from all of them.
2Ti 3:12 In fact, everyone who wants to live a godly life in Christ Jesus will be persecuted,
2Ti 3:13 while evil men and impostors will go from bad to worse, deceiving and being deceived.

Paul hoped for better things from Timothy, his son in the faith. Timothy was well aware of Paul’s life. And there could scarcely be a better example than Paul, of a mere mortal overcoming persecution. That example was not just for Timothy, but for everyone who wants to live a godly life in Christ Jesus. Paul showed that it could be done. The only question for Timothy, and for us, is whether we love Jesus enough to do likewise.

2Ti 3:14 But as for you, continue in what you have learned and have become convinced of, because you know those from whom you learned it,
2Ti 3:15 and how from infancy you have known the holy Scriptures, which are able to make you wise for salvation through faith in Christ Jesus.
2Ti 3:16 All Scripture is God-breathed and is useful for teaching, rebuking, correcting and training in righteousness,
2Ti 3:17 so that the man of God may be thoroughly equipped for every good work.

Paul reminded Timothy of the firm foundation for his faith. He knew the scriptures. He had learned the wisdom of God for salvation. He had everything he needed in order to set the same kind of example as Paul was setting. The challenge for Timothy was to fulfill what he already knew. As Jesus had said,

John 13:17 Now that you know these things, you will be blessed if you do them.

We need to make the scriptures our solid foundation. We need to let them impart wisdom, and then we need to live by that wisdom. In doing so we will be able to acknowledge the truth. We will learn to love what God loves, and to hate what God hates. And so we will be equipped to do God’s work faithfully in spite of persecution.


2 Timothy Chapter 2, part 2

May 14, 2010

As Paul contemplated his likely martyrdom, his concerns turned toward the future of the churches he had started. There were already signs that the message was drifting off course in some places. Constant vigilance was needed to keep non-Christian philosophies from polluting the message.

2Ti 2:14 Keep reminding them of these things. Warn them before God against quarreling about words; it is of no value, and only ruins those who listen.
2Ti 2:15 Do your best to present yourself to God as one approved, a workman who does not need to be ashamed and who correctly handles the word of truth.
2Ti 2:16 Avoid godless chatter, because those who indulge in it will become more and more ungodly.
2Ti 2:17 Their teaching will spread like gangrene. Among them are Hymenaeus and Philetus,
2Ti 2:18 who have wandered away from the truth. They say that the resurrection has already taken place, and they destroy the faith of some.

Paul drew a contrast between quarreling and godless chatter on one hand, and correctly handling the scriptures on the other. Men like Hymenaeus and Philetus were arguing against fundamental principles of the Christian faith, and were having a growing, harmful effect on the church. Paul called this “godless chatter.” Quarreling about words may have the appearance of taking the Word of God seriously, but Paul said it was of no value, and harmful to those who hear it. He challenged Timothy to learn to handle the scriptures correctly.

Hymenaeus and Philetus were saying that the resurrection has already taken place–that is, that there would be no future bodily resurrection. That would have been acceptable to Jewish Sadducees, and to some Gnostics. But it was false teaching and was destroying the faith of some. As Paul said elsewhere, if it is for this life only that we have hope in Jesus, we are of all men most to be pitied!

2000 years later, we still have a lot of quarreling and godless chatter. People like to fantasise about the visions in Daniel and Revelation. They quarrel about complex topics like predestination and free will. For many, Christianity has become a competition of intellects, a never-ending debate. And so they miss the whole point.

2Ti 2:19 Nevertheless, God’s solid foundation stands firm, sealed with this inscription: “The Lord knows those who are his,” and, “Everyone who confesses the name of the Lord must turn away from wickedness.”

Paul urged Timothy to focus his preaching on turning people from wickedness. Repentance and lordship are the solid foundation for Christian life. That’s not the most popular part of the message. But he charged Timothy with preaching it regardless of the personal risk in those dangerous times.

2Ti 2:20 In a large house there are articles not only of gold and silver, but also of wood and clay; some are for noble purposes and some for ignoble.
2Ti 2:21 If a man cleanses himself from the latter, he will be an instrument for noble purposes [even martyrdom?] made holy, useful to the Master and prepared to do any good work.
2Ti 2:22 Flee the evil desires of youth, and pursue righteousness, faith, love and peace, along with those who call on the Lord out of a pure heart.

God’s purposes are noble. He has noble plans for us. Certainly the job of preaching the Word is the most noble of callings. But to fulfill that calling, Christians must “flee the evil desires of youth” (you know what they are…) and pursue a different kind of life — one characterised by righteousness, faith, love, and peace. That was not just the standard for the minister, but for all those who call on the Lord out of a pure heart.

So how was Timothy supposed to address the quarreling and godless chatter while at the same time pursuing love and peace?

2Ti 2:23 Don’t have anything to do with foolish and stupid arguments, because you know they produce quarrels.
2Ti 2:24 And the Lord’s servant must not quarrel; instead, he must be kind to everyone, able to teach, not resentful.
2Ti 2:25 Those who oppose him he must gently instruct, in the hope that God will grant them repentance leading them to a knowledge of the truth,
2Ti 2:26 and that they will come to their senses and escape from the trap of the devil, who has taken them captive to do his will.

Paul taught Timothy that he was not to get involved in the quarrelling. Instead Timothy was commanded to teach with kindness, without resentment, with gentleness. Someone might ask, “How will kind and gentle teaching bring someone to repentance?” Paul provided the answer. It is not the minister, but God, who puts repentance in their hearts. Have faith that God will do his part!

After Paul departed from this life, false teachers arose and tried to lead the believers away. In addition to the Epicurean and Stoic philosophers came several varieties of Gnosticism. Paul wanted to be sure that after he was gone the leaders of the church would know how to oppose these heresies.

Today we still have to be prepared to oppose heresies such as these. Like Timothy, we must avoid quarrels and teach kindly and gently. It is God’s Word, and not our clever ideas, that will bring people to repentance. We need to preach the scriptures accurately, and to have faith that God will bring people to repentance.


2 Timothy: Chapter 2, part 1

May 12, 2010

2Ti 2:1  You then, my son, be strong in the grace that is in Christ Jesus.
2Ti 2:2  And the things you have heard me say in the presence of many witnesses entrust to reliable men who will also be qualified to teach others.

In chapter 2, Paul continued urging Timothy to be faithful in the face of persecution.  In contrast to some others Paul had just mentioned in the first chapter, he wanted Timothy to “be strong in the grace that is in Christ Jesus.”

At this point Paul began to introduce a new aspect of his concern related to the persecution.  It wasn’t just about Timothy.  Paul wanted to be sure the church was in good hands after he was gone.  He had just told Timothy about some trusted men who had deserted him as the risk of Roman execution increased.  So he urged Timothy to entrust the gospel to reliable [Gk pistos, faithful] men who would be able to teach others also. He didn’t want the leaders of the church to run and hide when the heat was turned up.

Paul urged Timothy to be faithful in enduring hardship with us. One can only wonder, who was this “us?”  Was Onesiphorus in prison with Paul now?  Is that why he mentioned the welfare of the household of Onesiphorus (2 Tim 1:16, 4:19).  Or were there others close to Paul who were also waiting on “death row?”  In any case, that is what Timothy must be willing to do if he were to endure hardship “with us.”

Paul then presented three brief parables about faithfulness for Timothy to ponder:

1) The soldier

2Ti 2:3  Endure hardship with us like a good soldier of Christ Jesus.
2Ti 2:4  No one serving as a soldier gets involved in civilian affairs—he wants to please his commanding officer.

Being a faithful servant of Christ is like being a good soldier. The NIV translation “civilian affairs” is unfortunate here. More true to the Greek is the ASV: “No soldier on service entangleth himself in the affairs of this life.”  He could not love this life and be a faithful servant of Jesus.   To be faithful, Timothy must have only one agenda: that of his Lord. There could be no excuses for shrinking back from preaching the whole gospel, including the unpopular parts.

2) The athlete

2Ti 2:5 Similarly, if anyone competes as an athlete, he does not receive the victor’s crown unless he competes according to the rules.

Here the athlete is the Lord’s servant, and the crown is eternal life. The rules are to be faithful. If Timothy were to shrink back, he would forfeit the crown.

3) The farmer

2Ti 2:6 The hardworking farmer should be the first to receive a share of the crops.

The point here is that Timothy should work hard now,to receive the reward later. Now is the time for work. Rewards come when the work is done.

Jesus also taught a parable on this topic:

Mat 24:45 “Who then is the faithful and wise servant, whom the master has put in charge of the servants in his household to give them their food at the proper time?
Mat 24:46 It will be good for that servant whose master finds him doing so when he returns.
Mat 24:47 I tell you the truth, he will put him in charge of all his possessions.
Mat 24:48 But suppose that servant is wicked and says to himself, ‘My master is staying away a long time,’
Mat 24:49 and he then begins to beat his fellow servants and to eat and drink with drunkards.
Mat 24:50 The master of that servant will come on a day when he does not expect him and at an hour he is not aware of.
Mat 24:51 He will cut him to pieces and assign him a place with the hypocrites, where there will be weeping and gnashing of teeth.

Being a hardworking farmer was not just a good idea. It would make the difference between heaven and hell. He must be faithful to the calling he received.

Paul reminded Timothy once again about what faithfulness was costing himself.

2Ti 2:8 Remember Jesus Christ, raised from the dead, descended from David. This is my gospel,
2Ti 2:9 for which I am suffering even to the point of being chained like a criminal. But God’s word is not chained.
2Ti 2:10 Therefore I endure everything for the sake of the elect, that they too may obtain the salvation that is in Christ Jesus, with eternal glory.

Paul endured faithfully, for the sake of the elect. The message was clear: Timothy must endure with the same kind of faithfulness.

Paul then wrote what must have become a hymn in the early church:

2Ti 2:11 Here is a trustworthy saying: If we died with him, we will also live with him;
2Ti 2:12 if we endure, we will also reign with him. If we disown him, he will also disown us;
2Ti 2:13 if we are faithless, he will remain faithful, for he cannot disown himself.

The hymn speaks for itself. The poignant words expressed everything about what Paul was thinking, praying, and meditating as he sat in prison. Would Paul acknowledge his faith in Jesus before the authorities at his execution? Or would he disown Jesus to save his own neck? His reward hung in the balance. Paul knew what he would do. In a very short while he would die with Jesus, and then would live with Jesus. The soon-to-be martyr urged Timothy to have the faith to do the same.

One can only imagine congregations singing this hymn with tears after learning of Paul’s execution… and then of Peter’s… and of countless others from week to week. I doubt they were in any mood to quarrel about words.


2 Timothy: Chapter 1

May 4, 2010

The pressure of a death sentence emerges from every line of 2 Timothy, starting from the very introduction.

2Ti 1:1 Paul, an apostle of Christ Jesus by the will of God, according to the promise of life that is in Christ Jesus,
2Ti 1:2 To Timothy, my dear son: Grace, mercy and peace from God the Father and Christ Jesus our Lord.

Paul reminded himself as well as Timothy of the promise of a life after this life. Paul’s ministry was part of God’s plan, and his imprisonment was no less a part of the plan. His martyrdom also was in God’s plan from the beginning of time.  Everything was happening for a reason.

2Ti 1:3 I thank God, whom I serve, as my forefathers did, with a clear conscience, as night and day I constantly remember you in my prayers.
2Ti 1:4 Recalling your tears, I long to see you, so that I may be filled with joy.

Paul was confident in that next life. He had served wholeheartedly for around twenty years, at great personal sacrifice. This final sacrifice would just be the natural conclusion of a life spent for God. But as the time approached, he wanted to see the one who was closest and dearest to him. History does not tell us whether that happy reunion ever occurred.

2Ti 1:5 I have been reminded of your sincere faith, which first lived in your grandmother Lois and in your mother Eunice and, I am persuaded, now lives in you also.
2Ti 1:6 For this reason I remind you to fan into flame the gift of God, which is in you through the laying on of my hands.
2Ti 1:7 For God did not give us a spirit of timidity, but a spirit of power, of love and of self-discipline.

Paul didn’t waste time getting to the point of the letter. His message to Timothy was for him to be faithful.  He encouraged Timothy for his sincere faith, and reminded him of the faith of his mother and of his grandmother (Sadly, there is nothing encouraging to say about the men in his family.)   He urged him to be a bold prophet of the Lord, through the power of the Spirit he had received.

I think modern day preachers have been unfair to Timothy on this point.  From what we see Paul urging Timothy in other places, he apparently was not timid by nature.  Does this seem like instruction that needs to be given to a timid preacher?

1Ti 5:1a Do not rebuke an older man harshly, but exhort him as if he were your father.

Or this?

2Ti 2:24 And the Lord’s servant must not quarrel; instead, he must be kind to everyone, able to teach, not resentful.
2Ti 2:25 Those who oppose him he must gently instruct…

Paul had sent Timothy into some pretty intimidating situations during his second (Timothy’s first) missionary journey. Timothy was no wimp.  So, what was the purpose of this message about timidity, right at the beginning of the letter, and recurring throughout?

Let’s set the context of the letter.  What was going on in Rome at the time?

In 64 AD, a great fire occured in Rome.  Nero, seeking to divert responsibility from himself,  blamed the on Christians.  According to the Roman historian Tacitus, in his Annals:

Accordingly first those were arrested who confessed they were Christians; next on their information, a vast multitude were convicted, not so much on the charge of burning the city, as of “hating the human race.” In their very deaths they were made the subjects of sport: for they were covered with the hides of wild beasts, and worried to death by dogs, or nailed to crosses, or set fire to, and when the day waned, burned to serve for the evening lights. Nero offered his own garden players for the spectacle, and exhibited a Circensian game, indiscriminately mingling with the common people in the dress of a charioteer, or else standing in his chariot. For this cause a feeling of compassion arose towards the sufferers, though guilty and deserving of exemplary capital punishment, because they seemed not to be cut off for the public good, but were victims of the ferocity of one man.

In the aftermath of the fire, we find Paul in prison in Rome, and some pretty well-known Christians were running to hide in the tall grass. We learn from verse 15 that the entire province of Asia had abandoned Paul, including two men named Phygelus and Hermogenes. (We know nothing more about these two than that they apparently had played a significant role in Paul’s ministries, and they had abandoned him. What a shame to be known for something like that!) And in 2 Tim 4:10, we learn that Demas, Crescens, and Titus had abandoned the apostle. It seems that nobody wanted to be too close to someone like Paul at a time when Christians were being fed to animals, nailed to crosses, and burned at the stake. Who could blame them?

Paul hoped for better things from Timothy. Paul urged the still-young evangelist to be faithful. But what would that mean?

2Ti 1:8 So do not be ashamed to testify about our Lord, or ashamed of me his prisoner. But join with me in suffering for the gospel, by the power of God,
2Ti 1:9a who has saved us and called us to a holy life—not because of anything we have done but because of his own purpose and grace.

Paul challenged Timothy not to be ashamed to testify about the Lord. Considering the kind of court in which Paul would soon be giving his testimony, Paul’s words must have cut right to the heart of Timothy.   And he challenged him not only to testify boldly about the Lord, but to be loyal to Paul as well.  He urged Timothy join him in suffering for Christ.   Being faithful meant being passionately loyal, even at the risk of his own life.  That kind of faithfulness would only be possible by the power of God.   After all, this was all according to God’s purpose and grace.

2Ti 1:9b This grace was given us in Christ Jesus before the beginning of time,
2Ti 1:10 but it has now been revealed through the appearing of our Savior, Christ Jesus, who has destroyed death and has brought life and immortality to light through the gospel.
2Ti 1:11 And of this gospel I was appointed a herald and an apostle and a teacher.
2Ti 1:12 That is why I am suffering as I am. Yet I am not ashamed, because I know whom I have believed, and am convinced that he is able to guard what I have entrusted to him for that day.

Again Paul reminded Timothy, and himself, that Christ had overcome death, and had promised immortality to his followers. So just as Paul was not ashamed, he urged Timothy not to abandon him out of fear. God will keep his promise.

2Ti 1:13  What you heard from me, keep as the pattern of sound teaching, with faith and love in Christ Jesus.
2Ti 1:14  Guard the good deposit that was entrusted to you—guard it with the help of the Holy Spirit who lives in us.

Paul did not merely want Timothy to be loyal to him. More important was for Timothy to continue to preach the truth boldly. Under persecution from the Roman government, Timothy nonetheless must continue to preach about sin, righteousness, and judgment. He must not let the message be suppressed out of fear.
Not everyone had been so bold.

2Ti 1:15 You know that everyone in the province of Asia has deserted me, including Phygelus and Hermogenes.

But there were also examples of faithfulness:

2Ti 1:16 May the Lord show mercy to the household of Onesiphorus, because he often refreshed me and was not ashamed of my chains.
2Ti 1:17 On the contrary, when he was in Rome, he searched hard for me until he found me.
2Ti 1:18 May the Lord grant that he will find mercy from the Lord on that day! You know very well in how many ways he helped me in Ephesus.

In spite of personal risk, Onesiphorus had diligently sought out Paul in prison. Paul hoped that Timothy would do likewise.

I wonder how modern American Christians would have fared under similar pressures.   And as I hear preachers talking about “timid Timothy” I wonder who the real timid ones are.

Editing to add:  In case anyone may think there is no risk of preachers going to prison for their faith in Western countries today, check out this news article.


2 Timothy: Introduction

May 1, 2010

Paul had worked together with Timothy for well over a decade before he wrote his second letter to the young evangelist.   He had first encountered Timothy in Lystra in about AD 51 (Acts 16), as a young man of around 20 years of age — perhaps younger.    Timothy so impressed the apostle that Paul persuaded the young believer to accompany him on his second missionary journey.

Timothy’s mother was a Jew, but his father was a Gentile.  No other mention is made of Timothy’s father in scripture.  But it is apparent that Timothy’s grandfather gave Timothy’s mother to a Gentile in marriage — something that was  forbidden in Mosaic law.  Some even hold that Timothy would have been forbidden to enter the Jewish assembly as a result.   Yet Paul chose Timothy as his apprentice in the ministry.

Even from the early days of their partnership, Paul trusted Timothy with important missions (generally along with another partner – Silas, Erastus…) to address needs in churches including Corinth, Thessalonica, Berea, and Macedonia.  But Paul and Timothy also spent much time together as they built and strengthened churches together.  Paul, who had no wife and no children of his own, considered Timothy as his own son.

Timothy was with Paul during his first imprisonment, where he was included as a co-author of the letters of Philippians, Colossians,  and Philemon.  Timothy is also mentioned as co-author of 1 & 2 Thessalonians and 2 Corinthians.

Paul’s first letter to Timothy appears to have been written from Macedonia .  That may have been Paul’s visit mentioned in Acts 20, around AD 58-59.  Perhaps more likely, it was during a later visit after being released from his first imprisonment.  If that were the case, the letter would have been written a year or two before Paul’s second imprisonment, during the time after the close of the book of Acts.

That Paul endured two separate imprisonments in Rome is established by several facts.  In this final letter, Paul spoke of having previously been saved from the mouth of the lion.   It is evident that during that event, Paul expected to be released and to return to his missionary work.   He even requested that Philemon prepare for him a guest room in anticipation of a visit.  In contrast, Paul had no such optimistic expectation of release in his second imprisonment.  (History records that Paul was beheaded under Nero’s rule in around AD 65-68.)

Furthermore, as Scofield explains in comments on Acts 28:30:

It has been much disputed whether Paul endured two Roman imprisonments, from A.D. 62 to 68 or one. The tradition from Clement to Eusebius favours two imprisonments with a year of liberty between. Erdman (W.J.) has pointed out the leaving of Trophimus sick at Miletus, mentioned in 2 Timothy 4:20 could not have been an occurrence of Paul’s last journey to Jerusalem, for then Trophimus was not left ; Acts 20:4; 21:29 nor of the journey to Rome to appear before Caesar, for then he did not touch at Miletus. To make this incident possible there must have been a release from the first imprisonment, and an interval of ministry and travel.

For yet more evidence of a second imprisonment, consider the case of Demas. He was with Paul during his first imprisonment (Col 4:14, Phm 1:24).  But at the time Paul wrote 2 Timothy, Demas had deserted Paul.  Paul attributed his desertion to his having loved this present world.  So it seems that Paul’s circumstances were quite different during that time, and formerly loyal friends were distancing themselves to save their own skin.

Knowing that he was facing martyrdom, Paul’s thoughts turned to his protégé.  Clearly Paul felt an urgent need to encourage Timothy to remain faithful in the current and future trials.  Now more than ever, Paul must have felt the pressure of his concern for the churches. So he began to write perhaps the most poignant of his letters, an intensely personal and heartfelt message to the one he considered his son.