Most gladly (2234) (hedeos from hedus/hedys = sweet) is an adverb which literally means sweetly, and figuratively as used in this passage means gladly or joyously. Hedeos thus speaks of the experience of gladness which is based primarily upon the pleasure one derives from the activity (in this case the activity of "boasting" about weaknesses)! There is a sweetness in such boasting, not because the experience "feels good" to our outer man, but because of the divine assurance that it will "yield good" in our inner man (cp 2Co 4:16, 17, 18 - observe from these great passages how a knowledge of the end result, fortifies us to fight the good fight in the midst of the experiencing of afflictions, weaknesses, etc). Such a sweet, joyous attitude is a reflection of Paul's total surrender/complete submission to His Lord. Hedeos refers to the sort of friendly indifference with which an audience may listen to this or that speaker (2Co 11:19) and the real pleasure that they may derive from so doing (Mk 6:20; 12:37). Spicq adds that hedeos was commonly used in secular letters in which the author (would)... ask his correspondent exactly what he wants, saying that he will do it willingly. In 250 BC: “Write if you need anything from us, for we will do it hÄ"deōs” (graphe de kai, ean tinos tōn par’ hÄ"min chreian echÄ"s, hoti gar hÄ"deōs poiÄ"somen, SB 7648, 8); in the second century ad: “But you also must make clear to me what you want; they will do it hÄ"deōs.” Pleasure is or is not derived from someone’s company (SB 4317, 10; 7572, 20; P. Oxy. 298, 33; 1218, 12). The word is also used in formulas of greeting, and takes on the nuances of willingly, gladly (Pap.Lugd.Bat. XVI, 31, 4), pleasantly, with pleasure, as in this epitaph for a black slave: “Learn, stranger, that I am Fortunatus, because I obtained from Fortune that which is pleasant for mortals” (SB 8071, 18; cf. SEG VIII, 464, 22). (Spicq, C., & Ernest, J. D. Theological Lexicon of the New Testament. 2:172-173. Peabody, MA.: Hendrickson. 1994) The root word hedus/hedys is used to describe wine in the Septuagint (LXX) translation of Esther 1:10 ("the king being merry"), an offering that is acceptable to God (Josephus, Ant. 12.47 "a very great and acceptable gift which I devote to God"), a sweet child (Corpus of Jewish Inscriptions: Jewish Inscriptions from the Third Century B.C. to the Seventh Century A.D. New York, 1975), a person who is pleasant to be with (C.P.Herm. 3, 5), and of “the sweet life.” Hedeos - 3x in 3v in the Septuagint (LXX) and 5x in 5v in the NT - Esther 1:10; Pr 3:24; 9:17; Mk 6:20; 12:37; 2Co11:19; 12:9, 15. Calvin comments that Paul adds most gladly, to show that he is influenced by such an eager desire for the grace of Christ, that he refuses nothing for the sake of obtaining it. (Commentary on Corinthians) Although Jesus used a different verb when He charged the hearers to rejoice and be glad in His "Sermon on the Mount", He nevertheless expressed a truth similar to that in 2Corinthians... "Blessed (makarios [word study] = fully satisfied independent of the circumstances, similar to Christ's grace which is satisfactory for every weakness!) are you when men cast insults at you, and persecute you, and say all kinds of evil against you falsely, on account of Me. Rejoice, (present imperative = command to make this your grace empowered continual response to insults, etc) and be glad, (present imperative = command for us to continually "jump for joy" in the midst of insults and persecutions! = those willing to become a "fool for Christ's sake" 1Co 4:10) for your reward in heaven is great (This truth should spur us to live this present life with a future focus - 1Pe 1:13-note, cp Col 3:1-note, Col 3:2-note, Col 3:3, 4-note, 1Jn 3:2,3, Php 3:20, 21-note) for so they persecuted the prophets who were before you. (Mt 5:11, 12-note) Comment: The only way one can continually "jump for joy" when being persecuted for Christ's sake, is (1) to do so supernaturally, infused with Christ's all sufficient grace which empowers such a paradoxical/antithetical response and (2) to truly receive and believe Christ's words regarding our future, great reward (cp 2Cor 4:16, 17, 18). In other words such a person sees by faith not by sight (2Co 5:7), their faith being founded upon the faithful Word of Christ (Ro 10:17-note) Whose promises are all yea and amen in Himself! (2Co 1:20KJV). Paul amplifies Jesus' teaching regarding the association of present suffering and future rewards writing... we suffer with Him in order that we may also be glorified with Him. For I consider that the sufferings of this present time are not worthy (axios [word study] - put temporal suffering on one side of the scale and eternal glory on the other side = simply no comparison!) to be compared with the glory that is to be revealed to us. (Ro 8:17b-note, Ro 8:18-note) Rather (3123) (mallon) is used here as a marker of an alternative to something, giving the sense "instead of". The idea is "rather than ask again for the weakness to be relieved". Notice that Paul illustrates the way to live a powerful, supernatural life, not by being forced to boast, but by making a conscious choice of one's will (volitional = the act of exercising one's will) to boast in his weaknesses. Such "paradoxical" boasting is always our choice beloved. But such boasting is never "pie in the sky" boasting, for it is always grounded on solid foundation of the Word of Truth which never fails, specifically in context the truth that weaknesses are the road to the victorious Christian life. The world does not understand this truth. We apprehend it. And so the world scoffs, that we choose to boast boast! (cp 1Cor 2:13, 14, 15). And so A T Robertson explains that Paul is saying... Rather than ask any more (thrice already) for the removal of the thorn or splinter most gladly will I glory in my weaknesses. Slowly Paul had learned this supreme lesson, but it will never leave him (Ro 5:2; 2Ti 4:6, 7, 8). As Piper says... God’s purpose over and through Satan’s harassment is our humility. Paul was in danger of pride and self-exaltation and God took steps to keep him humble. This is an utterly strange thing in our self-saturated age. God thinks humility is more important than comfort. Humility is more important than freedom from pain. He will give us a mountain top experience in Paradise, and then bring us through anguish of soul lest we think that we have risen above the need for total reliance on his grace. So his purpose is our humility and lowliness and reliance on him (cf. 2Cor 1:9, 4:7)