δὲ καί Prot 309b

οὐχ ἥκιστα δὲ καὶ τῇ νῦν ἡμέρᾳ:
and not in the worst way today also.
This is how I understand. The translation has it as: and especially so today, which I do not understand. Denniston says that de kai is almost equivalent to αὖ, which is not the case here.

To me it parses as “and not least also in modern times”.

Looking at the context, I guess he’s answering the first of the three questions asked him by his companion, whether the Homer quote still applies today.

I think the connective δέ follows οὐχ ἥκιστα because as a common litotes for μάλιστα it is taken as virtually a single unit, and adverbial καί is often used in these type of climactic moments.

I think that “especially” translation that Constantine quoted may be what’s making you think litotes (I had to look the word up, lol). And the καί is actually meaningful. He’s saying that he approves of the statement for Homer’s time, and also today.

εὖ [ἔχει], οὐχ ἥκιστα δὲ καὶ ἐν τῇ νῦν ἡμέρᾳ
It holds well, and not least in modern times

With μάλιστα, this is similar, though preferencing τῇ νῦν ἡμέρᾳ a bit more:
εὖ [ἔχει], καὶ μάλιστα ἐν τῇ νῦν ἡμέρᾳ

This would be closest to that “especially” English translation:
εὖ [ἔχει], μάλιστα δʼ ἐν τῇ νῦν ἡμέρᾳ

And this one is weird/impossible, imo:
εὖ [ἔχει], μάλιστα δὲ καὶ ἐν τῇ νῦν ἡμέρᾳ

A similar thing to this οὐχ ἥκιστα δέ, in how it fits into the sentence, would be οἶμαι δέ.

All this is just how I grok it anyway.

Socrates is answering the three questions in chiastic order:

(3) καὶ πῶς πρός σε ὁ νεανίας διάκειται;
εὖ, ἔμοιγε ἔδοξεν, οὐχ ἥκιστα δὲ καὶ τῇ νῦν ἡμέρᾳ· καὶ γὰρ πολλὰ ὑπὲρ ἐμοῦ εἶπε βοηθῶν ἐμοί.

(2) ἦ παρ᾽ ἐκείνου φαίνῃ;
καὶ οὖν καὶ ἄρτι ἀπ᾽ ἐκείνου ἔρχομαι.

(1) τί οὖν τὰ νῦν;
ἄτοπον μέντοι τί σοι ἐθέλω εἰπεῖν· παρόντος γὰρ ἐκείνου, οὔτε προσεῖχον τὸν νοῦν, ἐπελανθανόμην τε αὐτοῦ θαμά.

In any case, οὐχ ἥκιστα almost always means “especially, in particular” and καί is common with such expressions.

IMO, it doesn’t really mean “especially” or “in particular”, even if it’s translated that way, and you can see it especially when it gets paired with things like this:

Xenophon: οἶδ’ ὅτι δι’ ἐμὲ οὐχ ἥκιστα ἔπαθεν, ἴσως δὲ καὶ διὰ σέ, ὦ Κῦρε, οὐδὲν ἧττον

And Herodotus is always saying οὐκ ἥκιστα ἀλλὰ μάλιστα, which betokens a contrast. Again, IMO.

Woodhouse s.v. especially

adv. P. διαφερόντως, ἐν τοῖς μάλιστα, P. and V. μάλιστα, οὐχ ἥκιστα, etc.

LSJ s.v. ἥκιστος

οὐχ ἥ., freq. in litotes, above all, more than all, A.Ch.116; οἵ τε ἄλλοι καὶ οὐχ ἥ. Ἀθηναῖοι Pl.Prt.324c, cf. Tht. 177c, Smp.178a, al.; ἐπὶ πολλῶν μέν . . , οὐχ ἥ. δὲ ἐν τοῖς παροῦσι πράγμασι D.2.1, cf. Th.7.44, etc.: c. gen., οὐχ ἥ. Ἀθηναίων σέ, ἀλλ’ ἐν τοῖς μάλιστα Pl.Cri.52a.

CGL s.v. ἥκιστα

οὐχ ἥκιστα > by no means least > (i.e. > but especially, in particular> ).

The Brill dictionary translates it as especially, then τε is connective and και is adverbial and untranslatable

The dangers of dictionaries…also let’s not lead with Woodhouse, which in contrast to CGL and LSJ, errs too frequently to ever be much help with this sort of thing.

Now look first at the Xenophon that I quoted. I hope everyone would agree that it simply cannot mean “especially” there due to the following οὐδὲν ἧττον, and must mean something like the “not least” of understatement. The CGL’s “by no means least” is workable, but the stuff after “ie.” would not quite fit there. And in addition to my Herodotus mention, LSJ gives yet another “ἀλλά” contrast from Crito, which again forces “not at all the least” or similar.

Going the other direction, however, do we have a single instance where we are forced to say “especially” instead of “not least”?

Let’s look at LSJ list. LSJ says “frequently in litotes, above all, more than all,” and then gives a list of “A.Ch.116, Pl.Prt.324c, cf. Tht. 177c, Smp.178a, al.” where should expect to see this. But looking all of these up, I don’t personally see any of these where “especially” is necessary and understated “not least” is not possible (worded slightly different in the Aeschylus adverbial, of course). The Symposium 178a reference especially seems to reject anything going further than “by no means least”.

So we’re left with one meaning, “not least”, that fits everywhere, and another meaning, “especially”, that is forced nowhere (so far…maybe there are better examples than the LSJ list that could be given, or maybe I’ve misread somewhere). Are we sure that we aren’t looking at an extraneous barnacle of sense that has attached itself to this phrase?

It does mean “not least,” but the point is that it’s litotic, as it almost always is in English too. When we say “not least” in English, I don’t think we ever mean “very little though not the absolute least”, but instead something closer to “most of all, especially.” In fact I think you intuitively understood this in your original translation “and not least also in modern times,” which is fine (as far as οὐχ ἥκιστα is concerned), because the two languages overlap here. I was just trying to explain why δέ was postponed and how καί is working here, and I think it’s easier with explicit reference to litotes. Hope this helps!

It just takes a light touch to distinguish between understatement (not the least, but actually important) and maximal understatement (not the least, but especially important).

I’ve mentioned some quotations in this thread where the two are more easily distinguished. I suggest looking at those. Beyond that, all I can say is to put the dictionaries and commentaries and translations away for a few years, and spend a bunch of time reading Plato without his explainers in the room, and a person gets extremely attuned to his flow and the pattern of his Greek.