You see the ‘Fourth Cup’ explanation often in these discussions, but you have to keep in mind the following.
(1) This explanation heavily relies on how a Seder is celebrated in
modern times. I like to remind people that Jewish ceremonies as they are celebrated now does
not necessarily reflect exactly how they were celebrated 2,000 years ago - which is a lot of time to evolve and develop. The Jewish Publication Society commentary on the Passover Haggadah (pp. 6-7) itself admits:
Scholars are divided on the value of this description for understanding how the meal was conducted during the Second Temple period. Many agree that some of it does represent practice during the Second Temple, but there is disagreement about the details.
Any attempt to present the Mishnah as a source for Second Temple practice must take into consideration the fact that there are details in the Mishnah’s portrayal of the seder that were introduced after the destruction of the Temple.
We know that wine drinking was already part of the Passover Seder in the 1st century (aside from the gospels, the 1st-century BC Book of Jubilees 49:6 alludes to wine-drinking), but was there already a set ritual of the four cups? We don’t know.
Even today, Jews don’t even agree on what to call these four cups, if they even give them proper names at all.
(2) This explanation picks different details from different gospels and mash them together into one. Now admittedly it’s a common procedure among us Christians to conflate and harmonize different details from different gospels (the Nativity scenes during Christmas are a good example of this), but I think - in this case, and a few other ones, at least - that this cutting-and-pasting kind of stretches the gospels.
The fact is this. Matthew, Mark, and Paul (1 Corinthians 11:23-26) only mention Jesus passing a cup of wine once, after He had passed the bread to the disciples. Luke (22:17-21) has Jesus doing it twice: one before passing the bread and one “after the supper” (which corresponds with the cup of wine in Paul’s version).
The way I see it, in order to arrive at four cups you’ll have to either assume: (1) that there was an unmentioned ‘third cup’, since Luke already accounts for two of them (assuming that Matthew, Mark, Paul and Luke all describe the same cup being passed around); or (2) in a much weaker idea than (1), that each source was describing a separate cup: so you’ll add Matthew’s-Mark’s-Paul’s one cup with Luke’s two to arrive at three cups. (Fortunately, most sources I’ve seen seem to go with (1).) Either way, you’ll need to jump to John’s description of Jesus saying “It is finished” at the offer of wine vinegar for the fourth cup.
Fr. Nathan O’Halloran, SJ also criticized this conflation of John with the synoptic accounts to produce a ‘fourth cup’, and Drs. Hahn’s and Pitre’s failure to present it as what it is, a
hypothesis:
Brant Pitre, Benedict XVI, And Why The Pope Has It Right
Fr. O’Halloran rightly points out that the synoptic and the Johannine chronology are different. In the synoptics, the Last Supper (Thursday evening) is presented as a Passover meal; it was after “when they sacrificed the Passover lamb.” But when you go to John, he states both that the day Jesus was crucified (Friday) was still the ‘Preparation of the Passover’ (incidentally, when the Passover lambs were being slaughtered) and that the Jewish leaders had yet to eat the Passover meal.
Now there’s a whole industry trying to harmonize these two accounts together, or at least, determining which chronology is ‘more correct’ historically (something complicated by the fact that both chronologies are kind of theologically motivated: the last supper-as-new-Passover of the synoptics vs. John’s Jesus-as-lamb of God), but leaving that whole issue aside for now, as Fr. O’Halloran says, “how could John think that Jesus was finishing the Passover if in John’s Gospel, Jesus dies at the hour of the slaughtering of the lamb?”