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Is there a particular significance that orthotomeo is chosen, (as I understand it to mean, to cut out a single end product that is straight like a path or a straight mine shaft) as opposed to say katatomeo that implies multiple cuts, dissecting, multiple end products?

How should the verse read in English best in light of orthotomeo. Rightly dividing doesn’t seem to be the best choice of words because it implies at least two sections which if read this way can potentially seem to justify the idea of one explanation for Jewish Christians and another for Gentile Christians for example but I sense the Greek has the connotations to cut and produce one single end product, Christians. Orthotomeo a word Timothy that applies to everyone.

English Translations

“Do your best to present yourself to God as one approved by him, a worker who has no need to be ashamed, rightly explaining the word of truth.” ‭‭2 Timothy‬ ‭2:15‬ ‭NRSV‬‬

The cutting doesn’t seem to come out in this version. Whether that’s important or not I don’t know.

“Study to shew thyself approved unto God, a workman that needeth not to be ashamed, rightly dividing the word of truth.” ‭‭2 Timothy‬ ‭2:15‬ ‭KJV‬‬

Dividing suggests cutting but at least two byproducts

“Do all you can to present yourself to God as someone worthy of his approval, as a worker with no need to be ashamed, because he deals straightforwardly with the Word of the Truth.” ‭‭2 Timothy (2 Ti)‬ ‭2:15‬ ‭CJB‬‬

Straightforward comes close to the orthotomeo definition but somewhat ambiguous without the Greek context.

“Do your best to present yourself to God as one approved, a worker who has no need to be ashamed, rightly handling the word of truth.” ‭‭2 Timothy‬ ‭2:15‬ ‭ESV‬‬

This is a good interpretation but a deviation from the Greek I feel.

Why do you think orthotomeo is used and how should it best be translated to convey the Greek?

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Two good sources on this are BDAG and Ellicott which both produce similar results.

BDAG on "ὀρθοτομέω":

Found elsewhere independently of the NT only in Prov 3:6, 11:5 [in LXX] where it is used with "hodous" and plainly means 'to cut a path in a straight direction' or 'cut a road across country (that is forested or difficult to pass through) in a straight direction', so that the traveller may go directly to his destination. Then [2 Tim 2:15] would probably mean, guide the word of truth along a straight path (like a road that goes straight to its goal) without being turned aside by wordy debates or impious talk. …

Ellicott reaches a similar conclusion for 2 Tim 2:15.

Rightly dividing the word of truth.--Better rendered rightly laying out the word of truth. The Greek word translated in the English version "rightly dividing," literally signifies "cutting a straight line." It seems most correct to regard it as a metaphor from laying out a road (see Proverbs 3:6, in the LXX. rendering, where the word is so used), "or drawing a furrow, the merit of which consists in the straightness with which the work of cutting, or laying out, is performed. The word of truth is, as it were, a road which is to be laid out straightly and truly." So Ellicott. To affirm (see Alford and Huther-Meyer) that the notion of "cutting" had been gradually lost, and that the word already in the time of St. Paul signified simply "to manage rightly," "to treat truthfully without falsifying," and that the exact opposite is to corrupt or adulterate the Word of God (2Corinthians 2:17), seems premature. (Comp. Eur. Rhesus, 422, ed. Dindorf.)

In the third century, Clement of Alexandria (Stromata, 7), for instance, certainly uses the word in a sense in which the idea of "cutting" has been lost, when he writes orthotomia (a substantive) as an equivalent for orthodoxia--orthodoxy. It is not improbable that the use of the word here by St. Paul gave the word a fresh starting-point, and that gradually the original meaning passed out of sight.

It is entirely understandable how so many translations of the word are used in an attempt to fully render the Greek meaning. Clearly, Paul is encouraging Timothy to use straight talk that goes directly to the truth.

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The similar passage, using a similar word, Hebrews 4:12 :

... sharper (τομώτερος Strong 5114) than any two eged sword, dividing ( μερισμός Strong 3311) asunder soul and spirit, joints and marrow ...

likens the activity of the word of God to either surgery or, perhaps, warfare, the sharpness of the sword being necessary to slice apart the mechanical structure (joints or, immaterially, soul) and the living tissue (marrow or, immaterially, spirit).

The result is the division into parts as the OP mentions, μερισ being 'part' and μερισμός, the division into parts.

Thus the emphasis, in Hebrews, is purely on sharpness.

But in II Timothy 2:15, the analogy is to building and the necessity is to get a straight cut of material so that one ends up with straight edges and accurate, perpendicular, ninety degree corners, in the resulting structure, else there is danger of collapse through gravity.

Here, ὀρθοτομέω Strong 3718 is a matter of the same sharpness seen in the Hebrews text (and using a very similar word) but the addition of the prefix ὀρθός Strong 3717 gives the added meaning of straight or 'upright'. (In this contextual sense it might be rendered 'true').

A true cut leads to an accurate building, which, in the context of preaching and teaching the gospel in order to gather and edify and build up the church, the house of God, is a very suitable analogy.

Translations :

KJV : rightly dividing

YLT : rightly dividing

EGNT: straightly cutting

Tyndale: dividing justly

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Here is a Hebrew expression misunderstood and lost in translation. Cutting Straight it is. Not dividing or setting a straight path, but cutting straight.

A Hebrew scribe was judged by the errors he made. There was zero tolerance for writing the wrong Hebrew letter or missing it. He had to be shame-less, without reproach. His work begun with the first parchment, then adding the next and so on. But he had to make straight cuts in each so they would fit together and make the "sacred scroll" straight. So that the completed scroll would be one continuous straight roll of sealed parchments. This in order for the whole scroll to "rolled back" and kept safe in the "Ark".

The Greek words used in translation were commonly used by Greek diamond cutters at the time. They made straight cuts to allow the full beauty of "the light' to transcend the diamond stone.

Paul was reinforcing the righteous obligation that Timothy had with the Gospel, defending it from the emissaries from Jerusalem who were adulterating what Paul had preached before. Timothy had to preach and teach straight, without adding fables, or traditions, teaching Grace above the Law.

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