It is Wednesday evening of Passion Week and Jesus is celebrating the Passover with His disciples a day earlier than the religious leaders in Jerusalem. For the sighting of the New Moon that would have occurred fourteen days earlier is not always clear and can be ambiguous and subjective, leading to the discrepancy. Since Jesus often found Himself in opposition to the religious leaders, it is not surprising that His disciples understood His celebration of the feast to be the correct one as reflected in the synoptic gospels. But John, writing much later, came to understand the significance that the official celebration recognized by the religious leaders was the next day, so that Jesus died at the exact time they were sacrificing their Passover lambs.
After numerous predictions that He would be delivered up to the religious leaders and turned over to the Gentiles to be crucified, it was at this last supper that Jesus shocked His disciples that it was one of them closest to Him, sharing His bread, who would betray Him. It was also at this meal that Jesus instituted the Lord’s Supper as a reminder not only of His body that was given for us, but of our communion with Him and with one another by partaking of the same loaf, so that if one member suffers, all the members suffer with it, and if one member is honored, all the members rejoice with it (1Co 12:26). Hence those who like Judas partake of the sacred meal in an unworthy manner sin not just against Christ, but against all those who are a part of His body (1Co 11:27), while those who commune with Him in His suffering shall also rejoice with Him in His resurrection; see Rom 8:16-18, Phil 3:10-11.
Also in His institution of the Lord’s Supper, with the few short words, “This is my blood of the covenant, which is poured out for many for forgiveness of sins”, Jesus communicated the deepest truths of the gospel of our salvation. For only by having shown us the way to life through death by His heroic sacrifice on the cross and resurrection from the dead are we able to overcome our fear of death to follow Him in the way of the cross and die to sin so as to find redemption from the power of sin and atonement with God through His forgiveness, as well as deliverance from all the slavery to the god of this world that results from our fear of death. Much more, by following Christ in the way of the cross and uniting our life with His through the New Testament in His blood, we also come to share in His resurrection from the dead and His inheritance of the nations in the kingdom of God; cf. Luk 22:29-30.
Now, what else did Jesus say about the cup of wine that He had just given His disciples to drink from that represented His blood of the covenant? See Mat 26:29 and note the emphatic nature of Jesus’ words recorded in all three synoptics that uses double and even triple negatives to communicate that He would by no means ever drink of that fruit of the vine again until that day He would drink it new with them in His Father’s kingdom; cf. Mar 14:25. What exactly did Jesus mean by this? See also Luk 22:18. Considering that Jesus in fact drank sour wine (i.e., vinegar, a fruit of the vine) upon the cross just before He died, in what sense was His death the inauguration of the kingdom of God? Cf. Mat 27:46-51, Joh 19:28-30, 1Co 15:3, and notice that Mat 26:29 completes Jesus’ words in Mat 26:27-28, which may indicate that Jesus Himself did not drink from that third cup of redemption that recalled how the Lord would redeem His people with an outstretched arm and great judgments (Exo 6:6). For in fact He was about to drink from the cup of the Lord’s judgment that accomplished our redemption; see Isa 51:17,21-22, Mat 26:39, Joh 18:11.
Is there a sense in which the Lord is present and drinks wine anew with His disciples when they are gathered together in His name? See Mat 9:17 and recall that wine represents the teaching and spirit of truth that makes the heart of man glad in a spiritual sense. Throughout the law and the prophets, grain, new wine and oil were promised to God’s people as a blessing for covenant obedience to sustain their physical lives; see for example Gen 27:28,37, Deut 7:13, 11:14, etc., as well as 1Ti 5:23. The spiritual counterpart of these in the new covenant is the word of God, sound instruction and understanding, and the Spirit of truth that likewise sustain our spiritual lives; see Eph 5:18-19 and its parallel in Col 3:16; cf. 1Ti 6:3, 2Ti 1:13, 4:3, Tit 2:1.
Although there is this spiritual sense in which the kingdom of God has already come and the Lord is present and drinks from the fruit of the vine with His disciples every time they gather in corporate worship, even as the celebration of the Lord’s Supper exemplifies, is this the fullest sense to understand His words? Think: has the kingdom come in all of its fullness, and Jesus returned in power to drink anew with His disciples the fourth cup of Passover wine, the cup of praise, in celebration of their complete deliverance from the bondage of sin and having entered in to take complete possession of the land of their inheritance? See Exo 6:7-8, 1Co 11:26. In what way then were Jesus’ words in Mat 26:29 instrumental in establishing the Lord’s Supper not just as a memorial of His sacrificial death, but of the future fulfillment of all God’s promises for the establishment of His kingdom? What two words in particular does Matthew report, not recorded in the other gospels, that speak of the hope of His disciples from every age to share in those kingdom blessings? As so many of His disciples died without receiving that promise, what do His words also communicate about the sure hope of the resurrection? See Heb 11:39-40; cf. Job 19:25-27, 1Th 4:13-18. As Jesus’ first coming was marked by the new wine of His teaching about the new covenant, is it possible that His return to drink anew the fruit of the vine with His disciples will also be marked by an even greater revelation of spiritual truth? Cf. 2Th 2:8, and notice that the NAS appearance = brightness KJV, splendor NIV, manifestation NET.