When I studied on the Cornhill Training Course (1997-8), Chris Green came as a visiting lecturer and took us through the letter of 2 Timothy.
I clearly remembering him "flying a kite" when it came to 2 Timothy 4:6-18. The traditional understanding is that the time has come for Paul's departure, meaning his departure from this life. He's being poured out like a drink offering. He's finished the race (of his life of ministry), and the crown (eternal reward in heaven awaits).
Chris threw out a "what if". What if he's not leaving this life, but leaving prison. After all, the cloak he requests could be his travelling cloak. The scrolls and parchments could be the books he needs for future ministry. One stereotype you need to forget as you read 2 Timothy is that the recipient is "Timid Timothy". Timothy was everything but. The other, he suggested, was "Pessimistic Paul". 2 Timothy 4 is not about Paul being cold (so needing a cloak), bored (so needing reading matter), and lonely (so needing his friends). It's about Paul about to head out on mission.
It would seem Chris later decided against this view. Or, maybe, decided it was too speculative to put in print. In 2000 he published a short little commentary on 2 Timothy entitled "Finishing the Race" in which he wrote this:
"Despite attempts to show that Paul is expecting to depart from prison, most commentators continue to see this verse as a reference to Paul's death. What makes that conclusive is in a similar passage (Philippians 1:23) the same word departure is used and it clearly means 'to die' in that letter. So Paul is aware that his ministry is drawing to a close and that Timothy is going to have to step up to the line." (Page 143)
I'm not so sure, Chris. Unless a word is a technical one, with a specialist meaning, it need not mean the same in every place it's used. The word 'departure' in Philippians 1 is an argument weighing towards 2 Timothy 4:6 being his departure from this life, but it's not conclusive.
Reading it again, my eye is drawn to Paul's companions.
When Chris taught us on Cornhill, he painted the traditional view as Paul wanting his best friends with him. He suggested that he instead wanted his travelling companions. Let's look:
"Do your best to come to me quickly, for Demas, because he loved this world, has deserted me and has gone to Thessalonica. Crescens has gone to Galatia, and Titus to Dalmatia. Only Luke is with me. Get Mark and bring him with you, because he is helpful to me in my ministry." (2 Timothy 4:9-11)
Timothy, Mark and Luke are indeed Paul's travelling companions in Acts. If Paul was about to die in the arena (something he has just escaped, significantly, 2 Timothy 4:17), why would he want to pull those key individuals away from their areas of ministry just to be with him. In many ways, this letter provides his closing instructions to Timothy. He doesn't need a few month's journey each way just to go in more detail face-to-face. He even says that Mark is useful / helpful to him in his ministry, suggesting this is why he wants to see him. He doesn't want to see Mark so he can help Mark in his ministry. He wants Mark so Mark can help with his.
That's pretty persuasive in my opinion. But what I hadn't seen until today was what comes next.
Most New Testament letters end with various greetings. Paul sends greetings from some of those with him, and sends his own greetings to individuals with the recipient of the letter. 2 Timothy is no different:
"Greet Priscilla and Aquila and the household of Onesiphorus. Erastus stayed in Corinth, and I left Trophimus ill in Miletus. Do your best to get here before winter. Eubulus greets you, and so do Pudens, Linus, Claudia and all the brothers and sisters." (2 Timothy 4:19-21)
It's easy to skip over these greetings, but ask this question: Is Paul all alone in prison, needing his best friends with him? No. He has Eubulus, Pudens, Linus, Claudia and all the brothers and sisters. Assuming he wrote this from Rome, it sounds like he has all the friendship and fellowship of the Roman church (who so affectionately met him in Acts 28:15) to encourage and support him.
He doesn't need Timothy, Luke and Mark because he needs friends, or fellow-Christians. He needs them because he needs fellow-ministers.
Is that "conclusive" that Paul is departing prison in 2 Timothy 4? No. But the idea that he's about to enter a fresh sphere of ministry got under my skin, and the more I read 2 Timothy the more persuaded I become that this may be what's happening.