There were four times that participants in the Passover meal drank together, commonly referred to as four cups. This may have been the first of the four. If it was, Jesus evidently did not participate in the drinking of the following three cups (v. 18).473The other Gospel writers did not refer to the first cup, so this may have been the third cup, the so-called cup of redemption. This view assumes that Jesus did participate in the drinking of the first and second cups, which would have been normal. "From now on"or "again"(v. 18) could mean either after this cup or after this Passover. I favor the view that Jesus was referring to the cup, not the Passover, and that this was the third cup. Luke rearranged the order of events in the upper room considerably as comparison with the other Gospels seems to indicate. Matthew and Mark have Jesus saying what Luke recorded in these verses just after what Luke recorded in verse 20.
Jesus continued to lead by giving thanks to God and then encouraging the apostles to partake. His action was similar to making a toast. However, His announcement that He would not drink the fruit of the vine again until He did so with His guests in the kingdom was not customary. It reinforced His previous statement that the kingdom would come. Obviously Jesus was stressing the certainty of the kingdom's coming. This was necessary since His impending arrest and death would cause the apostles to question whether it would come.
