What does Matthew 26:40 mean?

Jesus is overwhelmed by sorrow at the anticipation of what is about to happen to Him. The Gospels depict His anguish beyond human comprehension (Matthew 26:36–38; Mark 14:34; Luke 22:44). Christ will not merely be mocked, beaten, tortured, and killed on a cross in great humiliation. He will bear the wrath of God the Father for the sins of humanity (1 Peter 2:24). He will experience some unfathomable, inexplicable strain in His relationship to the Father during that time (Matthew 27:46).

In this state of mind, He has prayed something shocking in both its honesty and humility. He has expressed His desire that, if possible, that these things would not happen. That's an entirely human, natural response, and means nothing more than that Jesus does not "want" to suffer such horrible things. In almost the same breath, however, Christ declares His absolute commitment to follow the Father's will and not His own (Matthew 26:39).

Now He returns to His three most trusted disciples. He has asked them to watch with Him while He prays. Perhaps He meant for them to watch in the sense of keeping a lookout to protect His privacy and solitude. Perhaps He meant for them to join Him in praying, even at a distance. Or, He might simply have wanted the comfort of their presence.

Instead, Jesus finds all three sleeping. It is very late at night by this point, and the disciples are also likely greatly troubled by the things Jesus has said to them. Luke writes that Jesus found them "sleeping for sorrow" (Luke 22:45). They've also come from the Passover meal and the four cups of wine. None of those serve as an adequate excuse, however. Jesus wakes them and asks, pointedly, if they could not have stayed awake for one hour to watch with Him.

He will ask them to watch and pray once more.