According to tradition, when a young Hebrew man and woman were to be betrothed, the groom poured wine into his cup and invited the woman to drink of it. It was up to her. If she drank from it, she was considered betrothed to him. If she did not, no marriage would take place. Paul tells the church in II Corinthians 11:2: "For I am jealous for you with godly jealousy. For I have betrothed you to one husband, that I may present you as a chaste virgin to Christ." When the bride drank of the cup, she drank of the marriage covenant or contract, accepting it.
Understanding this symbolism, it is no wonder that Jesus tells His disciples in Matthew 26:28, "For this is My blood of the new covenant, which is shed for many for the remission of sins." As we drink of His cup, we accept His invitation to be betrothed to Him and to be forgiven of our sins so we can be like He is—sinless, spotless, and without fault in His presence at the Marriage Supper.
Yet it means far more! Remember that "drinking the cup" meant to accept whatever that cup represented. When the mother of James and John approaches Jesus with her request to have her sons sit on each side of Jesus when He came into His Kingdom, Jesus replies with a question:
But Jesus answered and said, "You do not know what you ask. Are you [James and John] able to drink the cup that I am about to drink, and be baptized with the baptism that I am baptized with?" They said to Him, "We are able." (Matthew 20:22)
They do not take the cue from Jesus that they may have to drink more than they care to swallow! They answer affirmatively before they realize what Christ's cup contained. Jesus continues in verse 23:
So He said to them, "You will indeed drink My cup, and be baptized with the baptism that I am baptized with; but to sit on my right hand and on My left is not Mine to give, but it is for those for whom it is prepared by My Father."
What happened to them? James the son of Zebedee was the first apostle martyred, early on by Herod (Acts 12:2). Though John was the longest-lived of the twelve, apparently living nearly 100 years, he certainly suffered greatly at the hands of persecutors. Not only did he spend many years in exile on the Isle of Patmos, one tradition says he miraculously survived being boiled in oil! Beyond this, he had to watch the church disintegrate through apostasy and persecution.
Part of what Jesus' cup entails is suffering. When we drink of His cup, we are saying we are willing to suffer with Him and experience with Him whatever He ordains for us. We symbolically pledge that we are willing to walk down the same path He walked, with similar consequences.
We do not just drink the wine at Passover—we drink "of the cup" of Passover, meaning we are proclaiming our willingness to share in similar trials as Jesus did. We proclaim we are willing to endure whatever He has appointed for us as our lot.
We are also identifying ourselves with Him exclusively: We are cupbearers to the King of kings and to Him only. Psalm 16:5 says, "O LORD, You are the portion of my inheritance and my cup; you maintain my lot." The Eternal is our cup! Do we grasp the meaning of this? We cannot serve two masters (Matthew 6:24). We cannot simultaneously identify with Christ and Satan. Our lives, our actions, our words, our thoughts, continuously announce which is our father, God in heaven or Satan. Drinking of Jesus' cup means to live His way of life and renounce Satan's ways.