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Paul's appeal to Philemon on Onesimus's behalf begins with irony: he sets aside his apostolic authority, along with the more assertive, demanding argument it would yield, for a more gentle form of persuasion. In defining his relationship to the church along lines of friendship, finally stressing his need for Philemon's love (v. 9), Paul establishes that his intent is not coercive but collaborative.
O'Brien says that the word translated "boldness" (parresia) refers to Paul's openness to speak intimately to Philemon, and he contends that to understand this word in terms of political authority is incorrect (1983:287-88). Yet by coupling it with order, which usually refers to an authoritative demand given by one in a superior position over another, Paul suggests that candor is justified by his right to rule. That is, the apostle could make demands if he wanted; he could force Philemon on religious grounds to do what he asks. This passage may even be a caveat, warning Philemon that his position within the church could be imperiled if he fails to comply with Paul's request.
However, the opening conjunction, therefore, already indicates that Paul's appeal will correspond to his prayer for Philemon, in which he thanks God for his friend's love. His use of in Christ roots his appeal in a place where God's salvation is shared and where any legal or fraternal obligation Philemon feels toward Paul can only be deepened and secured. This is why Paul's appeal to Philemon is tendered on the basis of love. As Wright points out, Paul seeks a free decision rather than a coerced obedience, since this is the more loving and Christian way (1986:180).
The word translated "appeal" (parakaleo) is part of Paul's special vocabulary. In Paul's use, it rarely implies a contrast to a command that might have been made instead. Rather, Paul usually "appeals" for prayer for some personal difficulty or for others' support (for instance, Rom 15:30-31). This deeper logic informs our understanding of the passage. First, it provides another, more implicit link between Paul's appeal and his earlier prayer for Philemon: his request is based on the confidence of answered prayer that Philemon will act compassionately (splanchna) toward Onesimus and so increase the sense of partnership (koinonia) within their household congregation. Second, Paul's appeal naturally draws attention away from personal authority and to personal need: he is an old man and now also a prisoner. Paul's appeal is rooted, therefore, in his awareness of his own need for Philemon's generous support.
The meaning of old man (presbytes) is contested. Harris, agreeing with O'Brien (1983:290), prefers to understand it as "ambassador" (1991:259-60). But this would require us to substitute another, albeit almost identical, word (presbeutes) for the one Paul actually uses. Without textual support, even with Lightfoot's claim that the two are almost identical in meaning, I am reluctant to agree. Paul's appeal is not made as an "ambassador" of Christ but as an old man who has great emotional and physical need of Philemon's love. Against Wright, who argues for a symbolic meaning of age (1986:180), I think that Paul's advancing age and imprisonment have literally cost him dearly. The difficulty of his circumstances now obliges Philemon to come to his aid by granting his request. Paul's appeal is made within a culture where the request of an elderly person would be granted; not to do so would have been considered shameful (Bartchy 1992a).