Matthew 26:36-40

Mat 26:36 (KJB)
Then cometh Jesus with them unto a place called Gethsemane, and saith unto the disciples, Sit ye here, while I go and pray yonder.

The Garden of Gethsemane was probably located at the foot of the Mount of Olives. The name “Gethsemane” means either “Olive Oil Press” or “Oil Valley.” It was also about ¾ mile (1.2 km) east of Jerusalem. The exact spot is not known because when Titus came in 70 A.D. to destroy Jerusalem, he had all the trees surrounding Jerusalem cut down to prevent escapes and bringing in supplies. (Luke 22:39 KJV) And he came out, and went, as he was wont, to the mount of Olives; and his disciples also followed him. According to Luke, the Garden is where Jesus went to pray many times and it was this routine that caused Judas to know exactly where Jesus would be. Tonight would be no different as they went to the Garden and Jesus went to pray. He separated Himself from the disciples by a few yards and then began to pray.

Mat 26:37 (KJB)
And he took with him Peter and the two sons of Zebedee, and began to be sorrowful and very heavy.

Sorrowful - Saddened
Very heavy - deeply depressed

Just as Peter, James, and John were witnesses of the glory of Jesus on the Mount of Transfiguration, they would now be witnesses to the agony of Jesus. When Jesus began to pray, He already began to experience His suffering. As He prayed He was in a saddened state and was also deeply depressed because soon He would experience two things He never previously did, from all throughout eternity. 1) He would be taking on all the sins of the Elect. (2 Cor 5:21 KJV) For he hath made him to be sin for us, who knew no sin; that we might be made the righteousness of God in him. 2) He had never experienced being separated or forsaken by His Father. (Mat 27:46 KJV) And about the ninth hour Jesus cried with a loud voice, saying, Eli, Eli, lama sabachthani? that is to say, My God, my God, why hast thou forsaken me?

Mat 26:38 (KJB)
Then saith he unto them, My soul is exceeding sorrowful, even unto death: tarry ye here, and watch with me.

Sorrowful - Very sad, deeply grieved, or anguished

The saying “to be sorrowful even unto death” meant that a person was so sorrowful that it would be better that they were dead. This did not mean that Jesus was speaking about suicide but that His soul was in sorrow to the point of death. Jesus wanted Peter, James, and John to bear witness to the prayer which He was going to pray. Jesus was experiencing human emotions but these were the type which He would experience before His crucifixion. Jesus wanted these three disciples to watch with Him because the hour was fast approaching when he would bear the sins of many. (Mat 12:40 KJV) For as Jonas was three days and three nights in the whale's belly; so shall the Son of man be three days and three nights in the heart of the earth. This was the first night as he began to start suffering.

Mat 26:39 (KJB)
And he went a little farther, and fell on his face, and prayed, saying, O my Father, if it be possible, let this cup pass from me: nevertheless not as I will, but as thou wilt.

Just as Moses in Exodus 19 and Abraham in Genesis 22, Jesus now separated Himself from the disciples. He then fell on His face and prayed. To fall on one’s face is an expression of humility in prayer as both knees and face touch the ground. The term “cup” is the Old Testament normal figurative expression of judgment and suffering at the hand of God. (Psa 75:8 KJV) For in the hand of the LORD there is a cup, and the wine is red; it is full of mixture; and he poureth out of the same: but the dregs thereof, all the wicked of the earth shall wring them out, and drink them. Jesus had continued to pray with such fervor that His sweat was as drops of blood. (Luke 22:44 KJV) And being in an agony he prayed more earnestly: and his sweat was as it were great drops of blood falling down to the ground. When Jesus had prayed asking that the cup of suffering would pass from Him, He was in no way wavering in His commitment to do what He came to do. (John 12:27 KJV) Now is my soul troubled; and what shall I say? Father, save me from this hour: but for this cause came I unto this hour. Jesus was showing His human side when He asked if the cup could pass from Him but he showed His divine side by stating that nevertheless, not His will but the will of the Father had precedence. The cup of the cross was not what He was asking would pass but the separation from his Father and carrying the sin of all the Elect. Something we could never understand since Jesus was holy and never sinned. The one who never sinned would have all the sins of the Elect transferred to Him thus removing them from every Elect person born then and to be born in the future.

Mat 26:40 (KJB)
And he cometh unto the disciples, and findeth them asleep, and saith unto Peter, What, could ye not watch with me one hour?

Jesus was filled with anguish of soul because He is beginning the times of His suffering and He comes back to His disciples whom He asked if they would watch with Him for at least one hour and He found them all asleep. This may be a prophecy of how alert the Christians will be when the Lord returns on the last day. Jesus seemed disappointed with the disciples that they could not watch. He was disappointed but not bitter.