The essay explores the implications of Paul's description of himself as an ‘old man’ (πρεσβύτης) in Phlm. 9 for his rhetorical strategy, his psychological state and his social role. The essay first counters the interpretation of πρεσβύτης in Phlm. 9 as ‘ambassador’ and identifies the sources of the interpreters’ resistance to Paul’s description of himself as an ‘old man’. On the basis of demographic data, the essay suggests that Paul was a man of about sixty when he wrote to Philemon and that Paul would have aged prematurely in consequence of what he had suffered as an apostle. The essay then argues that Paul’s description of himself as an ‘old man’ functions in the argumentative rhetoric of his epistle both as a pathetic and an ethical appeal, simultaneously arousing pity and engendering respect. Finally, the essay contemplates the source of the ‘confidence’ shown by Paul in his appeal to Philemon, despite his senescence and imprisonment.