Paul’s two letters to Timothy and his letter to Titus are closely related in substance, form and historical background. Both 
seem to have been written from Macedonia while Timothy was in Ephesus (modern day Turkey) where Paul had hoped to join him, 
and Titus was in Crete where Paul had left him. Paul had planned on wintering in Nicopolis in Epirus where Titus was to later 
join him. But, by the time he wrote 2 Timothy, Paul was a prisoner in Rome; but, not before he had visited Troas and Miletus. 
The assumed attitude of his position was not hopeful. He felt that he would die soon. He was a lonely old man and he wanted 
Timothy to come to him to keep him company. This is the problem with these three books. This, however, was not the situation 
of his Roman captivity in 61 – 63, or of the journey that preceded it. Some critics argue the letters were written not by 
Paul but by a forger who put in these details to make the letter seem more authentic and as Pauline as possible. There is no 
proof that Paul died after his first captivity. As a matter of fact Acts 28:30 suggests that he was set free. It is not 
impossible that Paul made another journey, not to Spain as he had once planned (Rom 15:24-28) but in the east as he had 
planned a year ago from the writing in Philemon 22. It is most likely that Timothy and Titus were written about 65 A.D. on 
that journey through Crete, Asia Minor, Macedonia and Greece. The background of 2 Timothy seems to be a fresh captivity 
ending in Paul’s death, in that case this letter would be his last will and testament and must have been written shortly 
before his death in 67.

Paul wrote the two letters to instruct his two most loyal followers on how to conduct and organize and govern the communities 
he had confided to their care. There is no trace of the monarchic bishops of whom Ignatius of Antioch writes forty years 
later. There are signs however, that this development is taking place: Timothy and Titus are empowered to act as delegates of 
Paul. They are responsible for several communities; though they are not attached to any of them (Titus 1:5) They are living 
in an interim period where apostolic authority was in the process of being transmitted, since the Apostles themselves were 
dying. Not long after the death of Paul, this authority becomes vested in the college of presbyters, also known as the 
“bishop”. 

These letters are not written in the distinctive Pauline style. You will note that the Greek used in these letters is elegant 
and fluid. They flow smoothly without any of the fire and exuberance of the early letters and the vocabulary used is very 
different. Some critics have tried to explain this by saying that Paul was getting old, and that being in prison affected him. 
But Colossians, Ephesians and Philemon were written less than 5 years before, and Paul was not in prison when he wrote 1 
Timothy and Titus. Attempts have been made to separate the authentic sections from later additions, but these have not proved 
satisfactory. The alternative would appear to be that Paul, as in the case of Ephesians, but to a greater degree, must have 
given someone who was both disciple and secretary an unprecedented amount of freedom. Luke was with Paul at the time, (see 2 
Timothy 4:11) and many critics have maintained that they could detect similarities between his style and that of the pastoral 
letters.

This all must be viewed in the context of the world around them which was in flames. The Roman Empire only just put down the 
second Judean revolt. The first revolt of Bar Kochba was in the years 44-47 approximately. This was put down with such a 
vicious  and sadistic hand that it insured the second revolt in 70-77. The Roman Empire was very nearly overthrown by the 
Second Revolt. If it had not been for the fact that Rome threw everything she had at the Judean armies, she would have lost 
the Levant.  The rebels were so much in control of the land that they were able to mint coins. The documents found in the 
Cave of Letters to which we alluded last week is an example of the many hiding holes that the Judeans used to elude the 
Roman armies. And there were a lot of Roman armies. The Roman state of emergency is reflected in the fact that not only did 
Rome send her best generals to the area, Julius Severus, was sent all the way from Britain. In any other case sending Severus 
form Britain to Judea would have been considered a demotion, so it had to have been a desperate situation to have debased 
themselves over such a tiny country. Another striking measure of just how desperate Rome was is the transfer of a 
considerable number of soldiers from a military unit known as the Classis Misenensis to the Legio X Fretensis. Membership in 
the Classis did not require the highly prized Roman citizenship, however when they were transferred they become citizens. The 
Roman high command would never have authorized such a whole sale transfer (necessarily making them Roman citizens) had the 
situation not been extremely grave. 

The Legio XXII appears to have been lost in this war. Even Cornelius Fronto, teacher of Marcus Aurelius, deplores the enormous 
loss of soldiers in this war. Many argue about exactly how many soldiers were involved but even the low estimate that in 
addition to the two legions stationed in Judea; at least seven more legions were deployed by Rome. Upper limits suggest 12 to 
13 legions. 


About the year 39 Paul escaped from Damascus. About 43 Paul and Barnabas are in Antioch which is the center for Hellenistic 
Christians. In 49 Claudius drove the Christians from Rome. It isn’t until the year 50 that the oral tradition of Matthew and 
the Letter of James are written. In 50 to 52 Paul is in Lystra, Phrygia, Galatia, Philippi, Thessalonica, and Athens where he 
gives his sermon on the Areopagus.

In the winter of 50 to summer of 52 Paul is in Corinth and he writes the letter to the Thessalonians. In 53 Paul is on his 
third mission to Ephesus and Corinth. Paul stays in Ephesus for 2 ¼ years. After 56 he writes the Letter to the Philippians.