“Wherefore, though I might be much bold in Christ to enjoin thee that which is convenient,”
Accordingly, though I am bold enough in Christ to command you to do what is required — Paul asserts the apostolic authority (en Christō — in/with Christ's authority) and could issue categorical orders (epitassein). The acknowledgment of this power (tolmēs — boldness/courage) sets it aside voluntarily in verse 9, making the coming appeal more compelling. Apostolic authority is stated and then surpassed by the greater power of love.
Church Fathers on Philemon 1:8
Observe how cautious he is, lest any of the things which were spoken even from exceeding love should so strike the hearer, as that he should be hurt. For this reason before he says, “to enjoin you,” since it was offensive, although, as spoken out of love, it was more proper to soothe him, yet nevertheless from an excess of delicacy, he as it were corrects it by saying, “Having confidence,” by which he implies that Philemon was a great man, that is “You have given confidence…
Nicene & Post-Nicene / Ante-Nicene Fathers translations · public domain
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