Wherefore, though I might be much bold in Christ to enjoin thee that which is convenient,
Yet for love’s sake I rather beseech thee, being such an one as Paul the aged, and now also a prisoner of Jesus Christ.
Years ago, I was taught that when a passage of scripture begins with a “therefore,” you need to go back and see what it’s there for!” Poor grammar, but the idea is very helpful. Wherefore is one of those words that refers to back to what had just been written or spoken. So, to paraphrase Paul, he is saying,”So, because of your reputation for love of the saints, and your love of God, and your benevolence to me personally, I have something to ask of you.”
Much bold in Christ: Paul was concerned that Philemon would think him much to forward, too frankly speaking, about Philemon’s personal business; Paul, however, reminds Philemon that he is speaking “in Christ.” He is speaking under the authority of the Holy Spirit.
To enjoin thee: To pertain to what is due, duty, as was fitting.
Paul, under the authority of the Holy Spirit, saw Philemon’s duty toward Onesimus as that which was his duty; that which was fitting for a man of God.
Yet for love’s sake: Better even that duty, what Paul was going to ask of Philemon was for love’s sake. Love of God, love of righteousness, love of mercy–and love of “Paul the Aged.” I wondered at first if Paul was trying to gain the sympathy of Philemon because of his old age, but that wouldn’t be consistent with the character of Paul. So, I looked it up. It’s what I do :). The same word, aged, can also mean ambassador. An ambassador is usually used in relation to one who represents someone else. Here, Paul is literally an ambassador for Christ.
And he IS old, probably older than his years due to all he suffered during his ministry. And he was a prisoner of Rome, waiting for his death sentence to be carried out. He was certainly speaking from a position of authority! His advanced age was regarded in itself as a sign of his authority.
He says that he is a prisoner of Jesus Christ; that is, he was bound, in bonds, chained FOR Jesus Christ’s sake. He seems not to have considered his bondage to be a burden, but a moment in time before he went to meet Jesus face to face.