In Matthew, Jesus predicted His death four times (16:21; 17:22-23; 20:17-19; 26:1-2). The disciples responded to Jesus’ first three predictions in an inappropriate way. After Jesus first predicted His death in 16:21, Peter took Jesus aside and rebuked Him (16:22-23). Jesus then rebuked Peter and had to explain to the disciples what following Him meant (16:24-28). After Jesus’ second prediction of death the disciples were saddened (17:23), but then they inquired about who was the greatest in the kingdom (18:1). The request by James and John for places at Jesus’ right and left in His coming kingdom (20:20-23) comes immediately after Jesus foretold of His death for the third time (20:17-19). Jesus took this opportunity to remind them to be servants (20:24-28). The disciples struggled to understand Jesus’ mission and their place in that mission.
In Matthew 20:20-23 James, John, and their mother approached Jesus to make a request of Him. Matthew is the only gospel that records their mother making the request on their behalf. Chrysostom, an early church father, said the brothers’ request “was doubtless their own, but they put forward their mother to make it.”
They requested positions of honor and power in Jesus’ coming Kingdom. They desired to be placed on Jesus’ right and left hand. “The place on the king’s right is traditionally that of highest honor and authority, but when two people are concerned, that on the left is necessarily also included without any sense of inferiority (1 Kgs 22:19; Neh. 8:4).” Jesus had told the disciples when He sits upon His throne they would sit on twelve thrones and judge the tribes of Israel (19:28). James and John appealed for a place at Jesus right and left as quickly as possible so they could obtain the most honored seats.
Again, the context illustrates how untimely the brothers’ request was. The previous parable Jesus told was regarding the landowner who hired men at the beginning of day, then the third, sixth, ninth, and eleventh hours. The conclusion of the parable is: “So the last shall be first, and the first last” (20:16). Rather than seeking to be a servant and accepting last place, James and John want to be first.
Jesus responded by informing them they did not understand what they were asking for. Could they drink the cup that He was going to drink? Jesus will drink of the cup of God’s wrath (26:39, 42; this cup is often referred to in the OT Ps. 75:8; Isa. 51:17-23; Jer. 25:15-29; Ezek. 23:31-34), but in this context the cup is probably a generic reference to suffering.
Jesus informed the brothers that if this was truly their request, it was in fact an entreaty to suffer as He would. They did not understand their request. When the 10 other disciples heard what James and John had done, they were outraged. Their anger was probably because they wanted the position for themselves, not because the two brothers failed to understand Jesus’ earthly mission. Jesus took this opportunity to discuss what leadership and positions of power looked like in His kingdom. He instructed His disciples not to seek positions of power or to order others around, like the Gentiles, but to seek to serve each other. Jesus came to earth to serve and give His life as a ransom for many (20:28). They are called to imitate Jesus’ attitude of servitude.
Jesus’ death dominates this context. Jesus predicted His death (20:17-19). When He asked the brothers about the cup He was to drink, it is a reference to His suffering (20:22). Jesus stated one of the reasons for His coming was to give His life as a ransom for many (20:28). The disciples did not understand Jesus’ suffering or what would be required of them.
Truly, James and John did not understand the implications of their desire for positions at Jesus’ right and left hand. The phrase “at my right and left” only appears one other time in the gospel: when Jesus is hanging on the cross with two robbers – one at his right and the other at his left (27:38). To be at Jesus’ right and left is not a glamorous thing but means one will follow in His footsteps by suffering for Him.
Although forsaken by His disciples (26:56), there were several women who watched Jesus’ crucifixion from a distance (27:55-56). Three of these women are specifically named, and it is deeply significant that the final one to appear in the list was the mother of James and John (27:56). “The mother of Zebedee’s sons previously envisioned her sons sitting on both sides of Jesus’ throne (20:20-21), but now she watches Jesus’ cross with revolutionaries crucified on both sides of him.” While her sons did not understand their plea, their mother begins to comprehend what it means to be on the right and left of Jesus. While her sons are nowhere to be found, she grasps what discipleship is all about. The place of the disciples is not one of glamor or power but the willingness to suffer for/with Jesus. This woman has gained the insight her sons lack.
Jesus’ promise to James and John was not for positions of honor, but rather an assurance that they would suffer for His name. In the book of Acts, the first apostle to be executed for the cause of Christ was James (Acts 12:2). According to history, John died a natural death at an old age but was exiled to the island of Patmos (Rev. 1:9). James and John come to understand the place of a disciple of Christ and willingly suffered for Jesus’ name.
It is easy for us to criticize James and John in Matthew 20:20-23, but do we imitate their willingness to suffer for Jesus? If required, would we be willing to be on Jesus’ right and left at the cross? Do we seek to be servants or to be served? Are we looking for positions of power and honor among Christians or looking for the least of the brethren to serve?
 Manlio Simonetti, Ancient Christian Commentary on Scripture: Matthew 14-28, Vol. 1b (Downers Grove: InterVarsity Press, 2002), 115.
 R. T. France, The Gospel of Matthew, The New International Commentary of the New Testament (Grand Rapids: William B. Eerdmans Publishing Company, 2007), 757.
 David L. Turner, Matthew, Baker Exegetical Commentary on the New Testament (Grand Rapids: Baker Academic, 2008), 671.
by Nathan Peeler