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Preach the Word (v. 1-8)
This section is basically just Paul passing the torch on to Timothy. He's saying that he is about to die and he wants Timothy to continue on in his place. There's not a whole lot here beyond that, although I do have a few comments.
v2 Paul tell Timothy to always be ready to teach the word "in season and out". He also says that he should teach with patience.
I think "in and out of season" means he should not only be prepared when he's about to preach on the pulpit, but also to be ready for unexpected interactions and opportunities, for example if someone came up to him out of the blue and asked a question, or if he sees an opportunity to teach in everyday life. He also tells him to be patient when teaching, presumably with people who disagree with him or are having a hard time understanding a point he's trying to make. This is basically 2 good things wrapped up together in my opinion.
For the record, David Guzik's interpretation of this phrase is the same as mine.
v3-4 People will listen to teachers who "suit their own passions" and they will avoid the truth in favor of myths.
This seems to me to be talking about people switching to other religions. The language being used here isn't particularly kind, however, it's not particularly divisive either as we have seen in the past. While I'm not a huge fan of this verse, I'm not particularly inclined to put it in my bad pile either.
v6 "I am already being poured out as a drink offering..."
This verse I just found fascinating. It seemed like such a strange phrase so I looked it up. It seems that it is talking about strong drink, usually offered along with other sacrifices (which is pretty much what it sounds like). It seems strange to me that Paul would be a drink offering. I guess the fact that Paul sees himself as an offering at all is something, does he think his life itself has been a sacrifice to God? Does it say something that he has given up something precious for the sake of God?
Guzik said that Paul's head was not yet on the executioners block, but his heart was there. Is he not just going to die, but moreover he's going to be executed? I guess that changes things a touch.
Personal Instructions (v. 9-18)
Paul asks Timothy to come to see him as soon as possible. He says everyone has left him except for Mark. He mentions that no one was there with him at his first defense, implying there was some sort of trial, lending credence to the idea mentioned above about Paul being executed soon.
Paul also mentions that Alexander the coppersmith did him harm, but he will be repaid by God.
This is wishing revenge on someone through God. I suppose it is better than actually getting revenge yourself, but it still seems like a bad mindset to be in.
Guzik quotes Trapp who tries to argue that this is not a curse but rather a prediction. I say this is nonsense, Paul is clearly wishing the other guy gets punished by God.
Final Greeting (v. 19-22)
Again, he urges Timothy to come quickly and then says goodbye.
For the overview post (If you think I should add or remove stuff from this list please let me know, I think it would make good conversation)
4:2 Always be prepared to teach, also teach with patience
"preach the word; be ready in season and out of season; reprove, rebuke, and exhort, with complete patience and teaching."
4:14 Wishing for revenge through God
"Alexander the coppersmith did me great harm; the Lord will repay him according to his deeds."