What does Matthew 26:27 mean?
ESV: And he took a cup, and when he had given thanks he gave it to them, saying, “Drink of it, all of you,
NIV: Then he took a cup, and when he had given thanks, he gave it to them, saying, 'Drink from it, all of you.
NASB: And when He had taken a cup and given thanks, He gave it to them, saying, 'Drink from it, all of you;
CSB: Then he took a cup, and after giving thanks, he gave it to them and said, "Drink from it, all of you.
NLT: And he took a cup of wine and gave thanks to God for it. He gave it to them and said, 'Each of you drink from it,
KJV: And he took the cup, and gave thanks, and gave it to them, saying, Drink ye all of it;
NKJV: Then He took the cup, and gave thanks, and gave it to them, saying, “Drink from it, all of you.
Verse Commentary:
Jesus is once more saying surprising and difficult things to the disciples. He has just broken a loaf of bread and given each of them the pieces, telling them to eat while referring to the bread as His body.

Now Jesus takes a cup of wine. He gives thanks to God the Father for the blessing of the wine, perhaps using the customary prayer of thanks to the "Creator of the fruit of the vine." He distributes the wine to each of the disciples.

Jesus was using this moment in the Passover meal to introduce something new to the disciples and, through them, to the church that would soon be born. The requirements for the Passover meal included drinking four cups of wine. This was likely the time for the "cup of blessing." Jesus associates that cup, representing God's gift to Israel, with His own blood. He commands the disciples to drink it, with that specific command in mind.

In the following verse, Jesus describes what that cup of wine will now represent (Matthew 26:28; Luke 22:19).
Verse Context:
Matthew 26:17–35 begins with locating the room which will be used for the Passover meal. While they are eating, Jesus announces that one of His closest disciples will become a traitor. Judas discovers that Jesus knows it is him. Jesus introduces the concept of bread and wine as symbols of His sacrificial body and blood. After the meal, Jesus tells the disciples they will fall away that night and that Peter will deny Him three times. They insist that will not happen. Mark 14:10–31, Luke 22:3–23, Luke 22:31–34, and John 13:21–38 feature these events, as well.
Chapter Summary:
The Jewish religious leaders further their plots to arrest and kill Jesus, finding a willing traitor in Judas Iscariot. A woman anoints Christ with oil during a dinner at Bethany. Next, Jesus and the disciples hold the Passover meal in an upper room where Jesus predicts His arrests and introduces the sacrament of communion. Then Jesus prays in unimaginable agony in the garden of Gethsemane before being betrayed by Judas and captured. The disciples scatter. Before the high priest, Jesus explicitly claims to be divine. They convict Him of blasphemy and sentence Him to death. As this happens, Peter denies knowing Jesus and runs away in shame.
Chapter Context:
After a long series of teaching (Matthew 24—25), Matthew 26 begins with Jesus saying He will be delivered up for death. Christ is anointed at a dinner in Bethany and Judas agrees to turn Him over to the chief priests. Jesus holds a Passover meal with the disciples, predicts an act of treachery, and introduces the sacrament of communion. He tells the disciples they will run in fear and that Peter will deny Him, which happens just as prophesied. Christ prays in great sorrow in a garden and is then arrested and taken away and unfairly sentenced to death. After this, Jesus will be taken to the Roman governor, where Jewish leadership will press for Him to be executed as an insurgent.
Book Summary:
The Gospel of Matthew clearly shows the influence of its writer's background, and his effort to reach a specific audience. Matthew was one of Jesus' twelve disciples, a Jewish man, and a former tax collector. This profession would have required literacy, and Matthew may have transcribed some of Jesus' words as they were spoken. This book is filled with references to the Old Testament, demonstrating to Israel that Jesus is the Promised One. Matthew also includes many references to coins, likely due to his former profession. Matthew records extensive accounts of Jesus' teaching, more than the other three Gospels.
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