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As usual, let's start by looking at the wikipedia page for Philemon. Apparently Philemon was the leader of the Colossian church. The book is generally regarded as one of the undisputed works of Paul, neat.
Greeting (v. 1-3)
Mostly just a greeting, Paul says he's writing the letter from jail, and that in addition to Philemon, he intends for Apphia and Archippus to read this.
Philemon's Love and Faith (v. 4-7)
Philemon's love and faith are great, he should share them. v.6 "I pray that the sharing of your faith may become effective for the full knowledge of every good things that is in us for the sake of Christ"
This section is mostly just Paul telling Philemon how awesome he is. I found verse 6 interesting, Paul says he wants Philemon to share his love and faith and he hopes that it will give us knowledge. I guess it really highlights a way of thinking, if we get our knowledge directly from God (or from the spirit or something) then the best thing we can do for knowledge it to spend all of our time getting closer to God. All important knowledge will come as a consequence of that. It actually has a sort of logic to it, the problem is if you are wrong about God existing, or if you believe in the wrong God, it is a huge waste of time.
Paul's Plea for Onesimus (v. 8-22)
Philemon had sent his slave Onesimus to help out Paul, and now Paul is sending him back to serve Onesimus once again. Part of Paul wishes he could keep Onesimus near him instead, but he is sending him back to Philemon because he doesn't want Philemon to do something purely by command. (I'm guessing they had previously agreed that Onesimus would help Paul out for a specified amount of time and then be returned). Paul says he loves Onesimus and wants Philemon to accept him back as a brother, not as a slave. He says if Onesimus has wronged Philemon or owes him anything, the debt should be applied to Paul instead.
I actually like this section quite a lot, which is pretty remarkable since it does involve the topic of slavery. Let's actually hit that topic right away, in verse 16 Paul pleads for Philemon to release him from slavery and instead treat him as a brother. This is pretty awesome, as freedom has got to be one of the greatest things you could give to a slave. In fact, I could imagine a modern day reader might try to argue that this is an indictment of slavery as a whole. I think this is taking it a bit far, as the plea from Paul is a specific plea for a specific slave he has grown close to. This doesn't read to me as "slavery is bad, everyone deserves freedom", but rather it reads as "I love this person, please free him". That being said, the simple fact that there is an argument (even a tortured argument) within the bible that slavery should go away is a good thing.
As expected, Guzik tries to make this argument. He says "Paul effectively abolished the sting of the “master-slave” relationship and laid the foundation for the eventual legal abolition of slavery." and he quotes Bruce who says "What the letter to Philemon does is to bring the institution into an atmosphere where it could only wilt and die". This argument falls flat for me, as slavery was still around for another good 1800 years.
Paul says twice (v. 8-9 and 14) that he is in a position of power over Philemon and he could order him to do something, but he doesn't want that, he wants Philemon to act on his own accord. This is pretty cool. My understanding is that Paul is basically the pope of the early church. As he says, he could simply command Philemon to do whatever he wants him to do. But instead he makes it a request, and even sends Onesimus back to Philemon to fulfill their previous deal. Seems like a good way for a leader to act, trust your people to do what is right, encourage them, but give them some latitude.
In verse 18, Paul takes on Philemon's debt. This is pretty great as well, it gives Philemon no excuse to not free Onesimus. He is really going above and beyond to help this guy out. One thought I had was that since Paul was in jail, taking on his debt isn't a big deal, but I quickly abandoned that thought. Paul is in charge of the church, and presumably he is in charge of a great deal of resources at this point. Furthermore, he obviously cares greatly about the church, giving away the churches time and money is not something he would do lightly. The more I think about this, the more it seems like a very nice gesture. One final point here, in v22 Paul asks that a room be prepared for him, he clearly doesn't expect to be in jail for much longer, which is a further point in favor of Paul taking this debt very seriously
If I want to be nitpicky (and I do) there is one verse in this section I really don't like. v11 is talking about the situation where Onesimus was sent from Philemon to Paul, it says "formerly he was useless to you, but now he is indeed useful to you and to me." The way I read this is that Philemon owed Paul something, and he decided to pay him with a fairly useless slave. Paul says this in a fairly matter of fact way. It apparently makes sense to him that slaves are properly used as payment. This makes sense, as slavery was just a fact of life at the time, but it is part of what keeps this section from being an indictment of slavery in its entirety.
Well this is interesting, Guzik says that Onesimus ran away from Philemon and went to Paul. So him being formerly useless is because he had run away. Having run away, he was no longer in the possession of Philemon and is therefore useless to him. I'm not sure I am convinced, but this certainly seems consistent with what is written in the text. In verse 15, it says "this is perhaps why he was parted from you for a while". I interpreted this as him being traded, but perhaps it means he ran away. I tried looking at other translations to see if it helps, but it still seems pretty ambiguous to me. I tried looking at other translations, but it is not clear, I still think it reads more like a loan of a slave.
v19-20 "I, Paul, write this with my own hand: I will repay it--to say nothing of your owing me even your own self. Yes, brother, I want some benefit from you in the Lord. Refresh my heart in Christ."
This is interesting, he is trying to say that he will repay any debt that is owed to Philemon by Onesimus, and he follows up by pointing out what Philemon owes him. He basically says Philemon owes him his life since Paul saved him. Makes me think back to Pascal's wager, can you really say you lose nothing by believing?
One other stupid thing I'll mention, I don't really know what to make of this, but both Guzik and Gill noted that Onesimus means profitable. Is this actually a real story, or is it supposed to be a lesson and the characters are aptly named? It's not impossible that his name means profitable and he happens to be in a dispute over whether or not he is a profitable slave, but it sounds like lazy writing. To use an analogy, I'm sure there are some librarians with the last named Bookman, but if you saw one in a story with that name you'd probably judge the writer for it.
Final Greetings (v. 23-25)
Just says goodbye, nothing to see here.
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)
Phil 8-9, 14 making request is better than giving orders
"Accordingly, though I am bold enough in Christ to command you to do what is required, 9 yet for love's sake I prefer to appeal to you..."
"but I preferred to do nothing without your consent in order that your goodness might not be by compulsion but of your own accord."
Phil 16 Paul requests Onesimus be released from slavery
"no longer as a slave but more than a slave, as a beloved brother--especially to me, but how much more to you, both in the flesh and in the Lord."
Phil 18 Paul takes on Onesimus' debt
"If he has wronged you at all, or owes you anything, charge that to my account."
Phil 6 we gain knowledge through faith
"and I pray that the sharing of your faith may become effective for the full knowledge of every good thing that is in us for the sake of Christ"
Phil 11 it is implied that trading slaves is an acceptable form of payment
"Formerly he was useless to you, but now he is indeed useful to you and to me."
Phil 19-20 By being saved, your life is owed to the church
"I, Paul, write this with my own hand: I will repay it--to say nothing of your owing me even your own self. Yes, brother, I want some benefit from you in the Lord. Refresh my heart in Christ."
I've mentioned this before, and if I recall correctly, it has always gone in the other direction before. But simply counting the number of good versus bad is not a very good metric for judging how good or bad a book is. In this instance, I have 3 good things and 3 bad things, but I would not judge this book as equally good and bad. In my opinion, the bad things are more nitpicky, and in v11 it is an interpretation of mine that I'm not even particularly confident of (I still think it's worth mentioning though). The point is, even though we have 3 vs. 3 here, I would argue that this book is more good than bad if we examine the content more deeply.