This is part of my Exegetical Compilation Project, which can be found here.
Matthew 26:24: this verse (which is identical to Mark 14:21 except GosMark doesn’t include a verb for the sentence) is often appealed to as testimony against the salvation of Judas.
In order to understand it, first we must figure out who the pronouns in the verse refer to, which turns out to be somewhat difficult (even though I’m going to end up with the traditional interpretation for reasons I’ll explain below).
kalon (en) aut(i)o ei ouk egennethe ho anthropos ekeinos
kalon = good
(en) = was (found in GosMatt’s text, omitted from GosMark’s)
aut(i)o = a prepositional third person pronoun, but in a weird case: “him” with a preposition implied. Most translations go with “for” as the equivalent English preposition, but to be blunt that’s kind of a guess, as exemplified by Green who in his literal translation took the standard “for” but in his super-literal translation he didn’t bother even trying to supply a preposition!–but placed the implied “it” there instead.
ei = if
ouk = not
egennethe = was conceived
ho anthropos = the person
ekeinos = this is an odd reflexive term in Greek; it’s built from a word for “there” but is used for emphasis in regard to the noun it modifies (sometimes with its own direct article, though not this time). We would say in English “that there one”! Or “that selfsame one”.
The final clause certainly reads then: “if not was conceived that there person” or “that selfsame person” or “that very same person”.
The implication from the emphasis at the end is that the speaker is talking about a person he just recently referenced. By context, this can only mean Jesus or Judas; and almost certainly means the person being talked about in the first clause.
So if the “him” in the first clause is Judas, the second clause’s person is also (almost certainly) Judas. If the “him” in the first clause is Jesus, the second clause’s person is (almost certainly) Jesus.
Now however we get to another related use of {ekeinos}: a tool for helping authors distinguish between men when talking about two of them (especially in relation to each other). Is there another nearby use of “that very man”? Yes there is, back in the previous sentence (both in GosMatt and GosMark; also GosLuke for what it is worth although GosLuke doesn’t have either of the two clauses of the ending sentence.) “But woe to that-very man by whom the Son of Man is betrayed.”
By grammatic implication, the two “that-very” men are the same man, namely the one who betrays the Son of Man. So was the Son of Man betraying the Son of Man?! Matt 26:25, “And Judas, who was betraying Him…” starts the next sentence. (Also the preceding context reads, “One of you will betray Me”.)
This however opens back up the possibility that the “him” in the first clause of the final sentence does not refer to “that-very man”, since the term is definitely used for another purpose. It could of course be used for both purposes; but since “him” has already been used once in this statement and only for the Son of Man, then the parallels of usage would suggest that “him” refers to “Him” rather than to “that-very man”.
In the final analysis the grammar could be used either way: “him” in verse 24c (and its Markan parallel) could still be Jesus or Judas, although Judas is definitely “that-very man” at the end of 24c (and GosMark’s parallel).
Fortunately all this can be settled by cultural context much more easily–and, in passing, also lends weight to an interpretation of what we ought to be expecting from Christ in regard to Judas: the saying elsewhere (such as in Job) is a call for pity for that man of whom it would have been better had he not been born. (For the purpose of the saying, it is irrelevant whether the term is “born” or “conceived”; Job wished he had died in the womb after conception.) And that fits the term being used for “wail” or “woe” in all three Synoptics here: it means “lament” in pity.
That means the saying is in fact about Judas in both its clauses. But it isn’t a curse of hopelessness for Judas: it’s a cry for pity for Judas, expressing a wish that his situation would be mended. Jesus instructs His other disciples (and us too by extension) to be sorrowing in pity for Judas; to be hopefully loving him even in our grief for him.
(Compare also with comments to John 15:1-7, and its contexts, set a few minutes later in the same incident.)
Members are encouraged to add further discussion below, and especially links (both off-site and to threads on the forum) where these verses are being discussed elsewhere.
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IT make complete sense to me of the ‘data’ that this is a cry of pity rather than a curse 
about the ekeinos on the end and what it grammatically implies, taking everything else into account: it must refer (using a common Aramaic reflexive-for-emphasis form) to Judas. The distance between ekeinos and the prior use of ekeinos is irrelevant – it isn’t ridiculously far away, it’s still in topical range for reference, and much of the point to using the term at all would be to connect topics about who was being spoken of: Judas for sure in the first ekeinos reference, and Judas for sure in the second ekeinos reference. (Greek authors often use tools like this to help readers not get lost in the pronoun trails while they’re fronting other parts of the clauses or sentences for emphasis.)
), their argument is the same I made in my comments, that the dative to-him can refer to the Son of Man and that the distinction between the pronoun forms would normally be a signal linking (especially by an Aramaic figure of speech) that-very-many to that-very-man (i.e. Iscariot) in distinction from the man for whom it would have been better if that-very-man had not been born.