In studying Jesus' discussion with Nicodemus it is interesting to note the duplicate meaning of anothen and how Jesus could be using this duplicate meaning to probe Nicodemus' understanding of spiritual things. Since he takes the word to mean "again" rather than "from above" Jesus is able to then plunge into other spiritual topics to help bring Nicodemus into an understanding of the Spirit. Much more could be said about this word and the implications on their conversation, however, if the two were speaking in Aramaic rather than Greek, does that nullify this interesting piece of information about the Greek?
2 Answers
This answer goes along with the assumption of the question that Jesus and Nicodemus spoke Herew/Aramaic in this conversation. It shows that the double meaning of ἄνωθεν could have well been present in Hebrew/Aramaic. Thus, this is not a reason to say Jesus didn't speak with this double meaning.
While it's answering a similar but different question, this probably answers your question here: What does ανωθεν mean in John 3:3?
Basically, the Syriac (similar to Aramaic) Peshitta translates ἄνωθεν with word (ܕ݁ܪܻܝܫ) with the same root as רֹאשׁ. The prefixed ܕ݁ in Syriac shows an emphatic adverbial form like the suffix -ly in English (26. Adverbs, http://www.peshitta.org/beth-sapra/pdf_lib/eos01.pdf). It also has the dual meaning ἄνωθεν has. Words based on this root mean the head, the beginning and the top. This Hebrew word is used for the top of the ladder reaching to heaven in Jacob’s dream (Genesis 28:12). The word is used for the beginning of the year to express the Hebrew New Year (Rosh Hashanah), i.e. used for new. Thus, this indicates there is a possible Hebrew term that has the ambiguity of ἄνωθεν. The word ἄνωθεν is used for the top of the curtain in front of the Holy of Holies in Matthew 27:51.
At http://www.peshitta.org/ ܕ݁ܪܻܝܫ is translated "again" but has a footnote "Literally, 'From the start (over again).'” Thus, it can also mean "from the top" or "from above."
Similarity of Aramaic root to Herbrew root:
†[רֵאשׁ S7217 TWOT2983] n.m. Dn 7:6 head (Egyptian Aramaic, S-C; Palm. רש; 𝔗 רֵישׁ, Syriac ܪܺܝܫ (riš); BH רֹאשׁ);—cstr. ר׳ Dn 7:1; emph. ה—ָ 2:38; sf. רֵאשִׁי 4:2 +, ךְ—ָ 2:28, הּ—ֵ v 32 +, הּ—ַ 7:20, הוֹן—ֵ 3:27; pl. abs. רֵאשִׁין 7:6, sf. רָאשֵׁיהֹם (K§ 53, Anm. b); 63 Gu ad loc.) Ezr 5:10;— 1. head of man Dn 3:27, cf. 7:9; in vision: of image 2:32, 38, beast 7:6, 20. 2. head as seat of visions, הֶזְוֵי רֵאשָׁךְ, etc., 2:28; 4:2, 7, 10; 7:1, 15. 3. = chief, בְּר׳ Ezr 5:10 in the capacity of their chiefs. 4. sum, essential content, of matters Dn 7:1 (Nes 40 beginning). -- Brown, F., Driver, S. R., & Briggs, C. A. (1977). In Enhanced Brown-Driver-Briggs Hebrew and English Lexicon ([Aramaic section], p. 1112). Clarendon Press.
ܥܢܳܐ ܝܶܫܽܘܥ ܂ ܘܶܐܡܰܪ ܠܷܗ ܂ ܐܱܡܺܝܢ ܐܱܡܺܝܢ ܐܴܡܰܪ ܐ̱ܢܳܐ ܠܴܟ݂ ܆ ܕܷ݁ܐܢ ܐ̱ܢܳܫ ܠܴܐ ܡܶܬ݂ܻܝܠܷܕ݂ ܡܶܢ ܕ݁ܪܻܝܫ ܆ ܠܴܐ ܡܶܫܟܱ݁ܚ ܕ݁ܢܶܚܙܶܐ ܡܰܠܟܾ݁ܘܬ݂ܷܗ ܕܱ݁ܐܠܴܗܳܐ ܂ (John 3:3, Peshitta)
See also What does "born again" from John 3:3 mean?
Appendix Related to helping disciples remember
Jesus’ instructions were often, if not usually, uttered in rhythmic or otherwise memorable fashion. As Barnett notes, “Much of his teaching is cast in poetic form, employing alliteration [repetition of same sounds or letters], paronomasia [puns, wordplays], assonance [resemblance of sound], parallelism, and rhyme. According to R. Riesner, 80 percent of Jesus’ teaching is cast in poetic form.” At the least, this suggests that Jesus expected his disciples to learn from him, and learn well, both the content and the form of much of his instruction. -- Komoszewski, J. E., Sawyer, M. J., & Wallace, D. B. (2006). Reinventing Jesus: How Contemporary Skeptics Miss the Real Jesus and Mislead Popular Culture (pp. 37–38). Kregel Publications.
The word play is even more common when translating Jesus' words into Hebrew/Aramaic. This is not surprising since once what Jesus said was put into writing in the New Testament, memory was as much a concern.
Second, Jesus asks the pointed question, “If you have not been faithful in unrighteous mammon, who will entrust the truth to you?” (Lk 16:11, my translation). This text exhibits a play on words in Aramaic, which was the language Jesus spoke at home. He says:
If you have not been amin [faithful]
in the unrighteous mammon [your material possessions]
the amuna [the truth]
who will ja’min ith kun [entrust to you].
The root amn, which appears in the word amen, is used here four times. It makes the point that anyone who cheats on his or her taxes will never understand the gospel. Those who have been unfaithful before God with material possessions cannot expect God to reveal his greater treasure to them, which is the truth of God. -- Bailey, K. E. (2008). Jesus through Middle Eastern Eyes: Cultural Studies in the Gospels (pp. 378–380). Downers Grove, IL: IVP Academic:
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This is very insightful, and makes sense given the stated assumptions, +1 Commented Jan 10, 2022 at 22:58
Welcome to the site!
There are, broadly speaking, 4 possibilities:
The "accidental pun" theory: Jesus & Nicodemus spoke in Aramaic, and the word-play was not intended by Jesus. There are no early historians who substantiate this interpretation.
Jesus & Nicodemus spoke in Hebrew -- or at least had Hebrew OT passages in mind -- this possibility is explored effectively by Perry Webb on this thread and in his linked answer. The duplicate meaning would in this case have been intentional.
The conversation was invented years later by a Greek-speaking theologian and never really happened. This possibility fares poorly in light of the testimony of Irenaeus of Lyons, the Muratorian fragment, Clement of Alexandria, and 100% of the manuscript evidence attributing the 4th Gospel to John.
Jesus & Nicodemus had this conversation in Greek. Nicodemus, a member of the Sanhedrin, would have spoken Greek. For a review of the archeological & literary evidence that Jesus would have spoken Greek as well, see this video on my channel.
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+1 Note the qualification added at the beginning of my answer. Commented Jan 10, 2022 at 22:45