"My soul is overwhelmed with sorrow to the point of death. Stay here and keep watch with me." (Matthew 26:38)

Jesus told this to Peter, James and John ('the two sons of Zebedee') as he took them with him to go and pray at Gethsemane:
Then Jesus went with his disciples to a place called Gethsemane, and he said to them, "Sit here while I go over there and pray." He took Peter and the two sons of Zebedee along with him, and he began to be sorrowful and troubled. (Matt. 26:36-37)
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."

Ecclesiastical sectarian teachers would have us believe that Jesus' sorrow was related either to Judas' forthcoming 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, he only began to feel this way as he left them and went to pray. Why?

We must look at his prayers:
"My Father, if it is possible, may this cup be taken from me. Yet not as I will, but as You will." (Matt. 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." (Matt. 26:42)
Obviously, what is troubling Jesus is being expressed in his prayer, since 1) he only 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.

Let's break down the important elements of these two prayers:

The Greek word ποτήριον (potērion) is being translated to cup, as indeed it can refer to "a cup," or "a drinking vessel" according to the lexicon. At the same time, however, its metaphorical meaning is: "one's lot or experience, whether joyous or adverse, divine appointments, whether favourable or unfavourable, are likened to a cup which God presents one to drink: so of prosperity and adversity." This can also be summed up as someone's fate.

This is confirmed in Jesus' second prayer, as he does not use the word ποτήριον (potērion) at all, but rather, uses the word αὐτός (autos), which does not mean "cup" but rather, "this" or "these."

The next word (in both prayers), in Greek, παρέρχομαι (parerchomai) is being translated to "be taken" here. While it can mean "to go past" or "pass by" according to the lexicon, again we must apply its metaphorical meaning here, and according to the lexicon, this is: "to pass away" or "perish." In this application, it would be "to remove."

Then ἀπό (apo) is being translated to "from" here. This is appropriate, as its literal meaning is "to be separated from."

Then ἐγώ (egō) refers appropriately to the personal pronoun, "me."

So in the first prayer, Jesus is asking that a particular lot or fate be removed or taken from him. Why?

We learn more in the next part of his prayer.

The word πλήν (plēn) is being translated to "yet," but means "moreover, besides, but, nevertheless" according to the lexicon. While "yet" isn't wrong, this misses the point, which is that the Greek indicates something like "more importantly." "Notwithstanding" is another possibility, and πλήν has indeed been translated to "notwithstanding" in other verses of the New Testament. The essence of this is that Jesus was saying that the next thing he said in his prayer was "more important."

The next part is better translated in two phrases. The Greek phrase, οὐχ ὡς ἐγὼ θέλω indicates - and is appropriately translated to - "not as I will."  However, there is more depth to the phrase than even this. The word "will" translates from θέλω (thelō), which means, according to the lexicon, "to intend" or "to be resolved" or "determined" or "to purpose" or "to desire" or "to wish."

So the translation could just as well said, "not what I want" or "not according to my wishes".

The last phrase, ἀλλ’ ὡς σύ, indicates - and is appropriately translated to - "but as You will." However, the exact phrase is possessive, in that it does not contain the word θέλω (thelō) as the first phrase did. This might be said with something like "but Yours." In other words, "not my wishes, but Yours." But since this phrase is easily misunderstood, the translators have appropriately restated the word "will" here, as Jesus is saying "Not my will, but Your will." This could be rephrased as, "not what I want, but what You want."

As mentioned above, there is no "cup" in the Greek of the second prayer. The Greek word αὐτός (autos), is being assumed as "cup" only because Jesus used the word πίνω (pinō), which can mean "to drink" according to the lexicon. However, when πίνω is used in the figurative sense, it means, according to the lexicon: "to receive..."

Remembering that "cup" above metaphorically refers to one's lot or fate, and since αὐτός  used here better means to receive, we know Jesus is not talking about drinking or passing a cup here. Besides, a person does not drink a cup. A person drinks from a cup.

Then Jesus says virtually the same thing in the second part of the second prayer as the first prayer, but with conclusion instead of comparative selection. The Greek phrase is γενηθήτω τὸ θέλημά σου, which means "Your will be done." This utilizes the Greek word θέλημα (thelēma) which also indicates "will" but also "desires" or "wishes."

So while in the first prayer, Jesus is asking God to "remove" or "take away" his "lot" from him, in the second prayer he is supposing that if the only way his "lot" will be "taken away" is if he "receives" it, then this is what God wants him to do ("may Your will be done").

In the first prayer, Jesus says, "not what I want" or "not according to my wishes", but doesn't say that in the second prayer. In the second prayer, he is concluding that he will be doing God's will by "receiving" his fate.

It is evident that what is causing Jesus tremendous sorrow has to do with his knowledge of his fate, 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.

So we can see by Jesus' two prayers that he is struggling with what he wants verses 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." (Matt. 23:37-38)