Again

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ὅταν δὲ πάλιν εἰσαγάγῃYou ask if the text or the marginal reading in the A. V. of this clause gives the sense of the original. If we examine into the habit of the writer of this epistle when adducing quotations from the Old Testament, we shall be at no loss in determinining that πάλιν here is the mark of a new quotation, and not a note of time; for out of the ten occasions in this epistle on which the writer introduces this adverb (1: 5, 6; 2: 13, his; 4: 5, 7; 5: 12; 6: 1, 6; 10: 30) only three of them (5: 12; 6: 1, 6) can be said to express notations of time. Observe how this adverb comes in to mark a new quotation
1 Cor. 3:2020And again, The Lord knoweth the thoughts of the wise, that they are vain. (1 Corinthians 3:20); Heb.5; 2: 13, his.; 4: 5, 7; 10: 30). With this array of examples before us we can have no real difficulty, whether we examine simply the habit of the writer or the practice of those guided by the Holy Ghost, in determining that Heb. 1:66And again, when he bringeth in the firstbegotten into the world, he saith, And let all the angels of God worship him. (Hebrews 1:6) really means, " And again, when he brings the first begotten into the, habitable world."
The reference is to Psa. 97, quoted not with verbal correctness but for the sense of the passage, the point being that as angels are to worship Him when He comes into the universe as the firstborn, He must be superior to them, though he has appeared in the ranks of the human race. So whether the sacred writer had quoted verbally correctly, or only as he has done, the point of the quotation would remain the same. And the writer of the epistle does not always quote verbatim from the LXX. or from the Hebrew. Compare Heb. 1:77And of the angels he saith, Who maketh his angels spirits, and his ministers a flame of fire. (Hebrews 1:7) with Psa. 103:44Who redeemeth thy life from destruction; who crowneth thee with lovingkindness and tender mercies; (Psalm 103:4) in the LXX.; 2:12 with Ps. 21: 23 in the LXX.; 3: 10 with Psa. 94:1010He that chastiseth the heathen, shall not he correct? he that teacheth man knowledge, shall not he know? (Psalm 94:10) in the LXX. and XCV. 10 in the Hebrew; 6: 14 with Gen. 22:1717That in blessing I will bless thee, and in multiplying I will multiply thy seed as the stars of the heaven, and as the sand which is upon the sea shore; and thy seed shall possess the gate of his enemies; (Genesis 22:17) in LXX. and Heb.; 8: 11 with Jer. 31:3434And they shall teach no more every man his neighbor, and every man his brother, saying, Know the Lord: for they shall all know me, from the least of them unto the greatest of them, saith the Lord: for I will forgive their iniquity, and I will remember their sin no more. (Jeremiah 31:34) in Heb. and XXXVIII. 34 in LXX.; 10: 7 with Psa. 40:88I delight to do thy will, O my God: yea, thy law is within my heart. (Psalm 40:8) in Hebrew and XXXIX. 3 in LXX.
It is true that the words in Heb. 1 are found verbatim in the Vatican LXX. in Deut. 32, though in the Alexandrine LXX. we read, καἱ προσκυνησάτωςαν ἀυτῶ πάντεσ ὑιοὶ θεοῦ. But as neither the Hebrew, the Hebrew Samaritan Pentateuch, nor the Chaldee Targums, know anything of such words in Deut. 32:4343Rejoice, O ye nations, with his people: for he will avenge the blood of his servants, and will render vengeance to his adversaries, and will be merciful unto his land, and to his people. (Deuteronomy 32:43), nor the Vulgate or Syriac versions, we could not regard the Vatican LXX. as having preserved in that passage the words of the lawgiver