I sent him therefore the more carefully, that, when you see him again, you may rejoice, and that I may be the less sorrowful.
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EXPOSITORY (ENGLISH BIBLE)I sent him therefore the more carefully.—That is, I was the more earnest and anxious to send him. In any case the Apostle would have been desirous to express his thanks and send news by Epaphroditus. But the circumstances of his illness increased that desire to greater earnestness.
I may be the less sorrowful.—There is a peculiar pathos in this expression, as contrasted with the completeness of joy described above in Philippians 2:17-18. Epaphroditus’ recovery and safe return would take away the “sorrow upon sorrow;” but the old sorrow of captivity, enforced inactivity, and anxiety for the condition of the gospel, would remain. The expression of perfect joy belongs to the “spirit which was willing” indeed; the hint of an unspoken sorrow marks the weakness of the flesh.Php 2:28-30. I sent him therefore the more carefully — Or, speedily, as σπουδαιοτερως here signifies; that seeing him again — In a state of health, ye may rejoice — May be comforted after your trouble; and that I may be the less sorrowful — When I know you are rejoicing. Receive him therefore — With affection and gratitude, being assured that his long absence was owing, not to want of love to you, but to bad health; and hold persons of such a character, whatever their station of life may be, in great estimation. Because for the work of Christ he was nigh unto death — It appears from the last clause of this verse, that by the work of Christ here, the apostle partly meant his personal attendance on the apostle in his bonds, and the various services he performed for him, with his sundry journeys by land and sea on his account: but it is probable that he included also his labours in preaching the gospel in Rome, and in the neighbouring cities and villages, with his carrying the apostle’s messages and instructions to the disciples, his watching over them, visiting such of them as were sick, and other similar offices.
lest I should have sorrow upon sorrow—namely, the sorrow of losing him by death, in addition to the sorrow of my imprisonment. Here only occurs anything of a sorrowful tone in this Epistle, which generally is most joyous.I sent him therefore the more carefully; after his recovery, without delay, denying myself the comfort of his seciety, I have despatched him away to you.
That, when ye see him again, ye may rejoice; to the end that he whom you looked upon as dead might seasonably appear among you in person, and cheer you up in your troubles for him and me.
And that I may be the less sorrowful; and that I, who, by reason of your kindness to me, have occasioned his absence from you, might upon his safe return to you have somewhat to alleviate my grief, 2 Corinthians 6:10.
that when ye see him again ye may rejoice; for this must greatly increase their joy, to see him again after he had been so long from them, and under such a disorder, which had made them to fear they should never see him more. The Syriac version renders it, "that when ye see him ye may rejoice again"; as they had done heretofore in his conversation and ministry, when among them:
and that I may be the less sorrowful; when he should hear of his safe arrival among them, and of their joyful reception of him to their mutual satisfaction, which would be an alleviation of the apostle's sorrow in his present circumstances; for he did not expect to be wholly without sorrow while in this life.I sent him therefore the more carefully, that, when ye see him again, ye may rejoice, and that I may be the less sorrowful.
EXEGETICAL (ORIGINAL LANGUAGES)Php 2:28. The more urgently, therefore (in consequence of this sickness which he had had and recovered from, of which ye received tidings, Php 2:26-27), I have brought about his return, which otherwise I would still have delayed.
πάλιν] belongs to χαρῆτε, as Paul usually places it before the verb, or, at least, makes it follow immediately after. See Gersdorf, Beitr. p. 491 f., and van Hengel. And the context affords no ground for departing from the usual mode, and for joining it with ἰδόντες αὐτόν (Beza, Grotius, and others, also Baumgarten-Crusius and de Wette).
κἀγὼ ἀλυπότ. ὦ] Ἐὰν γὰρ ὑμεῖς χαρῆτε, καὶ ἐγὼ χαίρω, Oecumenius. He is not ἄλυπος, for he is in captivity and surrounded by adversaries; but the joy which he is aware is already prepared for his beloved Philippians by the return of Epaphroditus, lessens his λύπη. This tender interweaving of his own alleviation with the rejoicing of his readers is lost, if we refer ἀλύποτ. to the removal of the vexation of seeing the recovered one so full of longing and so uneasy (Hofmann), which, regarded as λύπη, would be sentimental. According to Weiss, Paul intends to say: still more ἄλυπος, than I have already become in consequence of Epaphroditus’ recovery. An unsuitable idea, because the comparative necessarily presupposes a certain degree of the λύπη still remaining. In the consciousness of this Paul has written ἀλυπότ.; if it had been otherwise, he would perhaps have used, as in Php 2:19, κἀγὼ εὐψυχῶ or κἀγὼ χαίρω.Php 2:28. σπουδ. The more regular form is the inferior reading σπουδαιότερον, which is due to some copyist. But that in -ως is also found in classical Greek. See W-Sch., p. 98. It is quite possible that we have here, as frequently in later popular Greek, a comparative with superlative force (see Blass, Gramm., p. 33). “I sent him with all haste” (including the notion of anxiety and concern which belongs to σπουδαῖος).—ἔπεμ. Epistolary aorist.—ἀλυπότ. Their joy means the lifting of a burden from his heart. He sympathised with Epaphroditus’ yearning for home. He sympathised with the Philippians’ anxiety for their brother. Chr. aptly quotes Paul’s own words in 2 Corinthians 11:29, τίς ἀσθενεῖ καὶ οὐκ ἀσθενῶ; τίς σκανδαλίζεται καὶ οὐκ ἐγὼ πυροῦμαι.
 Sch. Schmiedel’s Ed. of Winer.
 Chrysostom.28. I sent] In an English letter it would run, I have sent, or I am sending.
carefully] Better, with R.V. diligently; taking pains to arrange.
less sorrowful] A beautiful touch of character. Among his sorrows, he intimates, was his being the unwilling cause of separating Epaphroditus from the Philippians, and bringing him into risks at Rome. To think of him as safely returned to Philippi would be a solace, though it would be a new separation for himself.—Under the shadow of that last thought, perhaps, he says not “happier” but “less sorrowful.”Php 2:28. Σπουδαιοτέρως, the more earnestly, anxiously [carefully]) sooner than Timothy, Php 2:19.—χαρῆτε, ye may rejoice) Godly men may receive joy from all things.—ἀλυπότερος ὦ, I may be the less sorrowful) when I know, that you rejoice.Verse 28. - I sent him therefore the more carefully, that, when ye see him again, ye may rejoice, and that I may be the less sorrowful; rather, I send him (epistolary aorist, as Ver. 25), I send him with the letter. Perhaps "again" is better taken with the following clause; "that when ye see him, ye may again rejoice." Note St. Paul's ready sympathy with the Philippians: their restored joy will involve a diminution of his sorrow. Mark also the implied admission that sorrows must still remain, though spiritual joy brightens and relieves them. "Sorrowful, yet always rejoicing" (2 Corinthians 6:10).
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