The high priest Caiaphas hosts the chief priests and elders to plot to kill Jesus (Matt 26:3-4). Although they want to arrest Jesus, they do not want to do so during the Passover festival. The festival celebrates God redeeming Israel out of their slavery in Egypt, and so celebrates the origins of Israel as a nation. The large crowds gathered for Passover occasionally rioted when provoked. If Jesus was thought to be a king or a messiah, then arresting him could lead to dangerous riots and perhaps even a Roman intervention. See Josephus, War 2.223-227; Ant. 20.105-112.
To avoid a public arrest, they want to take Jesus “by stealth” (ESV) or “secretly” (NIV). The noun δόλος (dolos) refers to deceit or cunning, the related verb δολόω is used for false accusations, “to make false through deception or distortion” (BDAG). Most of us are familiar with politicians manipulating facts to get what they want. The high priest and his cronies are willing to say and do what it takes to get Jesus out of the way quietly. Ironically, they will get him out of the way, but not quietly!
Judas agrees to betray Jesus (26:14-16). After the anointing at Bethany, Judas Iscariot approaches the chief priests and offers to deliver Jesus into their hands. In Matthew, other than listing his name with the disciples, this is the first mention of Judas.Judas is a common name in the first century, looking back to Judas Maccabees as well as Judah, the patriarch whose tribe included David and the line of kings. John 6:71 adds that his father was Simon, another common name in the first century which refers to both a Hasmonean and patriarch.
The meaning of Iscariot is less clear. The word (Ἰσκαριώθ) It likely refers to Kerioth, a village in southern Judea, twelve miles south of Hebron. The meaning would be “Judas, from Kerioth” (BDAG suggests אִישׁ קְרִיּוֹת). Others suggest the name is related to an Aramaic word, seqarya, meaning “the false one” (Nolland, Matthew, 412). However, some scholars suggest the word is related to. σικάριος, a sicarii, an urban assassin or bandit. The Sicarii were active before the Jewish Revolt and were a major factor in destabilizing Jerusalem prior to AD 70.
Why did Judas betray Jesus? Matthew follows Mark by telling the story of the anointing at Bethany before Judas’s offer of betrayal. In Mark, “there were some” who objected (Mark 14:4), but Matthew is more specific, the disciples (οἱ μαθηταὶ) were indignant that the woman anointed Jesus with the expensive oil rather that give the money to the poor. John adds an important detail to the anointing story: the disciple who raised the objection to the woman’s waste of perfume was Judas (John 12:4), and John calls him a thief who was stealing from the moneybag (John 12:6).
The chief priests give Judas thirty pieces of silver (26:15) to help them arrest Jesus quietly. In Matthew 10:9 Jesus told his disciples not to take any money, yet now Judas takes 30 pieces of silver (Wilson, Matthew 14-28, 340. Wilson also comments: the chief priests seem to have extra money available for nefarious purposes!) In Mark 14:10-11 and Luke 22:3-6, the elders promised to give money to Judas, but no specific amount is mentioned. Matthew has added the detail of thirty pieces of silver (probably a denarius). Why?
There are two possible sources for the thirty pieces of silver. First, Exodus 21:32 states that if your animal accidentally kills someone’s slave, the slave owner was compensated with thirty shekels of silver. However, most commentators connect the thirty pieces of silver with Zechariah 11:12. A shepherd is paid thirty pieces of silver and then throws the money “into the house of the Lord, to the potter” (11:13). After he regrets his betrayal, Judas will throw his thirty pieces of silver into the house of the Lord (27:5) and the priest will buy a potter’s field with the money.
From that time, Judas began to look for an opportunity to betray Jesus (26:16). He was paid to “deliver” Jesus, so Judas is looking for a convenient time and place to arrest Jesus quietly, away from the Passover crowds.
Following Mark, Matthew puts the anointing at Bethany in the middle of the story of Judas offering to betray Jesus. Like Mark’s use of the cursing of the fig tree to explain the temple action (Mark 11:12-25). Why did Judas offer to betray Jesus? What provoked the Jewish leaders to arrest and execute Jesus before Passover? Both questions are answered by the anointing at Bethany.