πολλή μοι παρρησία πρὸς ὑμᾶς, πολλή μοι καύχησις ὑπὲρ ἱμῶν. If παρρησία means ‘boldness of speech’ (2 Corinthians 3:2), what is here expressed is, ‘am very frank in dealing with you; ‘I am full of boasting when I talk to others about you.’ If it means ‘confidence’ (1 Timothy 3:13; Hebrews 10:19), the thought is, ‘I am full of confidence in respect of yon; full of boasting on your behalf’ (2 Corinthians 5:12; 2 Corinthians 8:24); i.e. the internal feeling of confidence produces the external act of glorying. This is better. If the two clauses expressed a contrast, πρὸς ὑμᾶς and ὑπὲρ ὑμῶν would probably have stood first. For παρρησία in the secondary sense of ‘confidence’ comp. Wis 5:1; 1Ma 4:18. In this verse we have three of the key-words of this letter, καύχησις, παράκλησις, and θλίψις.

πεπλήρωμαι. ‘I have been filled and remain so.’ This is surpassed by ὑπερπερισσεύομαι, as τῇ παρακλήσει by τῇ χαρᾷ: the second clause is a balanced advance on the first. I am filled with comfort, I am overflowing with joy. In Romans 5:20 we have ὑπερεπερίσσευσεν ἡ χάρις: the verb is not found elsewhere in Biblical Greek. With the alliteration (π) comp. 2 Corinthians 8:22; 2 Corinthians 9:8; 2 Corinthians 10:6.

ἐπὶ πάσῃ τῇ θλίψει. This belongs to both clauses, as is shown by 2 Corinthians 7:6-7. The ἐπί indicates the occasions on which the comfort and joy were felt (Philippians 1:3). The thought of comfort and joy sends him back to the recent cause of these emotions.

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Old Testament