Philemon 1:8

“Wherefore, though I might be much bold in Christ, &c.] Or use much freedom of speech in the name of Christ, as an ambassador of his, and great authority as his apostle, which was given him for edification: to enjoin thee that which is convenient; which became him as a believer in Christ, and a minister of the Gospel; which was his duty, and was obligatory upon him, agreeable to the doctrines of Christ; who taught men to love their enemies, to be reconciled to their brethren, that had offended them, especially when they repented; and therefore it was fit and proper that he should receive his servant again, since God had called him by his grace, and given him repentance for his sins: upon this…”

“Wherefore--Because of my love to thee, I prefer to "beseech," rather than "enjoin," or authoritatively command. I might . . . enjoin--in virtue of the obligation to obedience which Philemon lay under to Paul, as having been converted through his instrumentality. in Christ--the element in which his boldness has place.”

“Wherefore, though I might be much bold in Christ - Though I might have much boldness as an apostle of Christ. He means that he was invested with authority by the Lord Jesus, and would have a right, as an apostle, to enjoin what ought to be done in the case which he is about to lay before him; compare 1 Thessalonians 2:6-7. To enjoin thee that which is convenient - To command what is proper to be done. The word “convenient” here (τὸ ἀνῆκω to anēkō), means that which would be fit or proper in the case; compare the notes at Ephesians 5:4. The apostle implies here that what he was about to ask, was proper to be done in the circumstances, but he does not put it on that ground, but rather…”

“I might be bold in Christ - Through the authority he hath given me. Philemon 1:9”

“1:8-9 The reason why Paul was asking a favor was Philemon’s reputation as a gracious, loving person (1:5-7). Paul could demand it by his authority as Christ’s apostle, but love leads Paul to request rather than demand. • Paul, an old man: Paul appeals to the respect due to older people as well as to his status as a prisoner for the sake of Christ Jesus, which would only increase a fellow Christian’s respect.”

“bold: Co2 3:12, Co2 10:1, Co2 10:2, Co2 11:21; Th1 2:2, Th1 2:6 enjoin: Co2 10:8 Philemon 1:9”