Mark 14:21 (RSV) reads
For the Son of man goes as it was written of him, but woe to that man by whom the Son of man is betrayed! It would have been better for that man if he had not been born.
Later in Mark's account of the passover in the upper room, we have the following (14:23):
And he took a cup, and when he had given thanks he gave it to them, and they all drank of it.
I'm interested in the interpretation of the phrase "It would have been better for that man if he had not been born" along with the implication of the phrase "they all drank of it."
How would the twelve have understood the former phrase? Was it common vernacular of the day? I know that a similar phrase appears in Ecclesiastes 4:3, but I'm unsure if this would have come to mind in the upper room, or if it was understood that Jesus was referencing Ecclesiastes. If it wasn't a common saying, what exactly does Jesus mean by this phrase, or what is Mark's purpose for including it?
Furthermore, it would appear that in Mark's account Jesus includes Judas (one of the twelve) in the initiation of the new covenant. Mark makes this clear by emphasizing that they (the twelve) "all drank of it." Is Mark making any commentary here about whether or not Judas has a part in Jesus' covenant? If so, how is this reconciled with Jesus' (rather harsh) statement about Judas' birth?