"My soul is overwhelmed with sorrow to the point of death." (Matthew 26:38)

He took Peter and the two sons of Zebedee along with him, and he began to be sorrowful and troubled. Then he said to them, "My soul is overwhelmed with sorrow to the point of death. Stay here and keep watch with me." (Matthew 26:37-38)

Why Jesus became sorrowful

Why did Jesus become "sorrowful and troubled" and "overwhelmed with sorrow to the point of death"?

The word "sorrow" here is being translated from the Greek word περίλυπος (perilypos) which means, "very sad" and "exceedingly sorrowful" according to the lexicon, and "so much as to cause one's death."

Sectarian teachers would have us believe that Jesus' sorrow was related either to Judas' betrayal, Peter's denial, or both. If this were true, why did he ask Peter with the other two disciples to come with him?

And why did he only just begin to feel sorrowful and troubled? The word "began" comes from the Greek ἄρχω (archō), which means to "be first" or "to begin." It is clear this was the first indication of Jesus' being sorrowful and troubled.

If Jesus felt sorrowful and troubled about Judas betraying him or about Peter denying him, or even about his disciples abandoning him, this would have become evident when he pointed out these forthcoming events in the previous conversations.

Rather, the reason for his sorrow was reflected by his prayer to the Supreme Being.

Jesus' prayers of sorrow

"My Father, if it is possible, may this cup be taken from me. Yet not as I will, but as You will." (Matthew 26:39)
and then a few minutes later,
"My Father, if it is not possible for this cup to be taken away unless I drink it, may Your will be done." (Matthew 26:42)
What is troubling Jesus is being expressed in his prayer, since 1) he became troubled just before his prayers; and 2) he was so troubled about it that he prayed about it twice. It is also logical that Jesus (or anyone) would pray about something that was troubling him.

The secret to his sorrow, then, lies within his prayers. And these prayers also unfold the very nature and essence of who Jesus was.

It is evident that what is causing Jesus tremendous sorrow has to do with his knowledge of his coming ordeal, which he knows will be his forthcoming arrest and execution - as he indicated previously his foreknowledge of these events in his previous conversation with his disciples.

Jesus was struggling with this

So we can see by Jesus' two prayers that he is struggling with what he wants versus doing God's will - what God wants.

Why is this important at this moment? Because Jesus knows that he will be arrested in a few minutes, and he could easily escape at that very moment. He could walk away, and avoid his arrest and execution.

In other words, Jesus could have run off into the night, changed his clothes and looks, and escaped to another part of the country. He could have completely deflected his arrest and persecution.

And Jesus was struggling with this. He asked three of his disciples to join him as he went off to pray, so they could keep watch, and allow him to pray without being arrested in the middle of his prayer. They would be able to warn him if someone was approaching. This is because at that moment he was not resolved. He needed to pray about whether he should escape arrest or not.

Jesus' struggle, his prayer and eventual resolve gets at the heart of who Jesus was. How so?

First, it indicates that Jesus was not the Supreme Being. Because he had desires separate from God, and struggled with doing God's will in this situation, we know that Jesus was not God.

Second, it indicates that Jesus had free will. He could have chosen not to do God's will. He could have run off and lived out the remainder of his life on the sea as a fisherman or something. The Romans and High Priests would have certainly left him alone, as he would not longer threaten their authority with his teachings. Jesus could have altogether avoided the tremendous suffering of being whipped and crucified.

Third, this indicates that Jesus wrestled with his choice. He was "troubled" and even "sorrowful" that he was thinking of his own comfort. He first prayed to God to prevent the whole thing from happening. He didn't want to be arrested and crucified. He preferred that God take it all away.

Fourth, Jesus ultimately sees that this is what God wants, and decides he will do what God wants. He will stand his ground and stand behind his teachings. He will stay at the camp site, where he knows that Judas will bring the Roman guards and high priest to have him arrested, tried and executed.

This indicates clearly that while Jesus was an individual with choice, he chose to be God's loving, devoted servant. He chose to do what the Supreme Being wanted him to do even though his body would suffer. This fact is confirmed by another statement by Jesus:
"For I have come down from heaven not to do my will but to do the will of Him who sent me." (John 6:38)
This means that while Jesus was sent by God, God still granted Jesus the freedom of choice to serve Him or not. As such, Jesus did struggle with his upcoming arrest and persecution because he knew his physical body would suffer. But Jesus ultimately did what God wanted, because he loved God, and wanted to please God:
"... for I seek not to please myself but Him who sent me." (John 5:30)
This is the meaning of loving God: Wanting to please the Supreme Being with our lives. Caring more about what He wants than what we want.

This is what Jesus did, and this is what Jesus taught:
"'Love the Lord your God with all your heart and with all your soul and with all your mind.' This is the first and greatest commandment." (Matthew 23:37-38)