As with Ecclesiastes, an obvious question about Philemon is: How did it get admitted to the canon of Scripture? Ecclesiastes contradicts Judeo-Christian teaching, but, perhaps boosted by the (false) notion that King Solomon was the author, it slipped past the gatekeeper. The subject matter of Philemon seems private and secular, but Paul wrote it, and everything in existence that was written by Paul, or that might have been written by Paul, is in the New Testament. An extant Pauline grocery list would likely have been canonized and subjected to close scholarly analysis for what it might reveal about, say, the relationship between his actual practice and the view of the Jewish dietary laws that he elsewhere expressed.
The letter to Philemon, however, is somewhat more interesting than a list, and scholarly analysis has revealed a dimension that would never be detected by any general reader of an unannotated translation. The situation, if not every detail, may be apprehended from the letter itself, which is very brief. While in prison, Paul has become acquainted with a fugitive slave, Onesimus, whose owner, Philemon, is a Christian. Roman law, like the American constitution, provided for the return of fugitive slaves to their owners. Paul, therefore, in order to comply with the law, is sending Onesimus back to Philemon, and he includes this letter explaining his intent and asking for clemency for the slave, who has been "useful" (Paul's word) to him.
Possibly a preternaturally alert reader might pause at this word "useful." Since the letter indicates that Onesimus has been converted to Christianity, it might suggest that he has also assisted Paul in his missionary work. And maybe he did. Still, in a sentence such as--
Formerly he [Onesimus] was useless to you [Philemon], but now he is indeed useful to you and me.
--the meanings of "useless" and "useful" are opaque and the words may appear to be working too hard: there is a sense of straining. The explanation, for most of us a retrospective one since we will have glided over the difficulty, is that in Greek "onesimus" means "useful." So Paul is here indulging himself in a bit of word play. It's like if, in our language, there was a rake named Randy and someone were to say of him--wink, wink--that "he is indeed randy."
That Paul was capable of a bit of linguistic frolicking is of some modest biographical interest, since playfulness of any kind is not usually associated with his writing--or with the New Testament in general, whose central figure, though "truly human," never laughs. Recognizing the pun also makes sense of the obscurity in the sentence quoted above. Paul is saying that the Onesimus known to Philemon is not the Onesimus who is now returning to him. He's transformed. Formerly he was useless (not worthy of his name) but he is now indeed Onesimus.
More than that, however: perhaps not just this one passage, but the whole letter, is a double entendre, in the sense that it says one thing on the surface even though Paul intends for the recipient to understand something quite different. I've set out above the surface meaning. Beneath the surface, Paul is telling Philemon that he wants Onesimus sent back to him--that he is not to be kept by Philemon as a slave. Usually my mind is set against any interpretation that has to it even a whiff of secret-coded-text intrigue, especially in the Bible. These are the verbal equivalent of conspiracy theories concocted by industrious enthusiasts determined to arrive at some predetermined conclusion. In the case of this letter, however, what I'll call the wink-wink interpretation has considerable explanatory power: it makes sense of things that otherwise seem a little odd. For example, the punning on the name "Onesimus" carries through the letter. The sentence quoted above is verse 11 (the whole letter is a single chapter of 25 "verses"). Here are verses 20-21, the beginning of the conclusion:
Yes, brother, I want some benefit from you in the Lord. Refresh my heart in Christ. Confident of your obedience, I write to you, knowing that you will do even more than I say.
The word "benefit" is a synonym of "useful" and an alternate pun on "Onesimus": that is, "I want some benefit from you in the Lord" may be construed as "I want Onesimus from you in the Lord." This does not seem to me to be much of a stretch. Indeed, under some allegedly more natural interpretation, it is unclear what benefit Paul is expecting to receive from Philemon. The next sentence, concerning Paul's wish that his heart be refreshed in Christ, may seem like a cant phrase, but in the context of this letter it is notable that, at verse 12, he had asserted that Onesimus was his (Paul's) "very heart":
I am sending him back to you, sending my very heart.
Thus "refresh my heart" acquires an undertone of "reunite me with Onesimus (by sending him back to me)." And then the clincher, the last wink of the wink-wink interpretation:
. . . I write to you, knowing that you will do even more than I say.
Paul is here acknowledging, winkingly, that his real meaning is not the surface meaning. The "more" that he expects from Philemon is the return of Onesimus. If you don't understand it this way, then you have to account for what else Paul is expecting from Philemon, for he never plainly says. Moreover, the indirection is not gratuitous but, considering the Roman law on the status of slaves, quite possibly prudent. Wayne Meeks, editor of the Norton Critical Writings of St. Paul, puts it this way:
The Roman laws governing fugitive slaves were strict, and Paul observes the legal necessities punctiliously. Anyone aiding a fugitive was liable for all damages due to the master . . . . Above all, the fugitive had to be returned; and Paul is sending Onesimus back. At the same time, Paul's half-stated request, the subtle pleas, the almost bantering tone of his several puns, render the legal situation so incongruous as to shatter it.
In other words, the indirection provides a prudent cover, what we now call "plausible deniability." I don't think it's the reason the letter to Philemon was canonized, but it's nevertheless true that, compared to his doctrinal writings, this more private letter shows Paul's character in quite a favorable light.
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