τοιοῦτος ὢν ὡς : “ τοιοῦτος can be defined only by a following adjective, or by οἷος, ὅς, ὅσος, or ὤστε with the infinitive; never by ὡς ” (Vincent). It seems, therefore, best to take τοιοῦτος ὤν as referring to … μᾶλλον παρακλῶ, which is taken up again in the next verse; ὡς Παῦλος … Ἰησοῦ must be regarded as though in brackets; τοιοῦτος ὢν would then mean “one who beseeches”. πρεσβύτης : this can scarcely be in reference to age, for which γέρων would be more likely to have been used; besides, in Acts 7:58, at the martyrdom of St. Stephen, the term νεανίας is applied to St. Paul. Lightfoot in his interesting note on this verse, says: “There is reason for thinking that in the common dialect πρεσβύτης may have been written indifferently for πρεσβευτής in St. Paul's time; and if so, the form here may be due, not to some comparatively late scribe, but to the original autograph itself or to an immediate transcript”; and he gives a number of instances of the form πρεσβύτης being used for πρεσβευτής. If, as seems very likely, we should translate the word “ambassador” here, then we have the striking parallel in the contemporary epistle to the Ephesians 6:20, ὑπὲρ οὗ πρεσβεύω ἐν ἁλύσει. Deissmann (Licht vom Osten, p. 273) points out that both the verb πρεσβεύω, and the substantive πρεσβευτής, were used in the Greek Orient for expressing the title of the Legatus of the emperor. Accepting the meaning “ambassador” here, the significance of the passage is much increased; for Christ's ambassador had the right to command, but in merely exhorting he throws so much more responsibility on Philemon. The word “ambassador” would be at least as strong an assertion of authority as “apostle”; to a Greek, indeed, more so. δέσμιος : perhaps mentioned for the purpose of hinting that in respect of bondage his position was not unlike that of him for whom he is about to plead; cf. the way in which St. Paul identifies himself with Onesimus in Philemon 1:12 … αὐτόν, τοῦτʼ ἔστιν τὰ ἐμὰ σπλάγχνα, and Philemon 1:17 … ὡς ἐμέ. Χριστοῦ Ἰησοῦ : belongs both to πρεσβύτης and to δέσμιος, cf. Philemon 1:1; Ephesians 3:1; Ephesians 4:1; 2 Timothy 1:8.

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Old Testament