What is the connection between שכל (intelligence), אשכל (loss of a child, as in Genesis 27:45), and אשכול (grape cluster)?

ANSWER:I’m sure you realize you’re making some assumptions here, so the basics first need to be clarified: Although the letters שׂandשְׁare certainly related, they are not synonymous; in fact, in my informal research I’ve found a much closer relationship between שׂandס than the former two.

Also worthy of note is that while Radak indeed links אשכלtoשׁכול, Menachem lists them in separate entries, with no apparent connection between them. That said, I do suspect (since I haven’t done a comprehensive study on it) that they are all related, but the basic relationship is because of the shared כלbiliteral, which includes meanings like completion,inclusion,consumption,destruction(which meanings are shared in other words denoting completion likeתם).

Still I would offer this partial suggestion at least to connect אשכלandשׁכול, based on the Targum Yerushalmi which translated one of the encampments named נַחַל אֶשְׁכֹּל (Num. 13:23), as נַחַל סְגוּלָה, and the אשכולthat the Spies cut there is called סְגוֹל דְעִנְבִין. To me, this suggests that the word אשכלrefers not to a cluster of grapes alone, but to a valuable, desirable entity, as we find in the later meaning of סגולה,treasure.

Anאשכל fairly begs to be picked, but while the picker gains the cluster, the vine has in a sense lost some it’s best and juiciest. The analogy to children taken in their prime become is clear (except for who stands to gain in that case).