The Problem of the Agony in the Garden

The episode is related in each of the synoptic Gospels:²

Then Jesus came with them into a country place which is called Gethsemani; and he said to his disciples, "Sit you here, till I go yonder and pray." And taking with him Peter and the two sons of Zebedee, he began to grow sorrowful and to be sad. Then he said to them, "My soul is sorrowful even unto death: stay you here, and watch with me." And going a little further, he fell upon his face, praying, and saying, "My Father, if it be possible, let this chalice pass from me. Nevertheless not as I will, but as you will." And he came to his disciples, and found them asleep, and he said to Peter, "What? Could you not watch one hour with me? Watch you, and pray that you enter not into temptation. The spirit indeed is willing, but the flesh weak." Again the second time, he went and prayed, saying, "My Father, if this chalice may not pass away, but I must drink it, your will be done." And he came again and found them sleeping: for their eyes were heavy. And leaving them, he went again: and he prayed the third time, saying the selfsame word. Then he came to his disciples, and said to them, "Sleep you now and take your rest; behold the hour is at hand, and the Son of man shall be betrayed into the hands of sinners. Rise, let us go: behold he is at hand that will betray me." As he yet spoke, behold Judas, one of the twelve, came, and with him a great multitude with swords and clubs, sent from the chief priests and the ancients of the people. [Matthew 26:36-47]

And they came to a farm called Gethsemani. And he saith to his disciples, "Sit you here, while I pray." And he took Peter and James and John with him; and he began to fear and to be heavy. And he said to them, "My soul is sorrowful even unto death; stay you here, and watch." And when he was gone forward a little, he fell flat on the ground; and he prayed, that if it might be, the hour might pass from him. And he said, "Abba, Father, all things are possible to you: remove this chalice from me; but not what I will, but what you will." And he came, and found them sleeping. And he said to Peter, "Simon, do you sleep? Could you not watch one hour? Watch you, and pray that you enter not into temptation. The spirit indeed is willing, but the flesh is weak." Going away again, he prayed, saying the same words. And when he returned, he found them again asleep, (for their eyes were heavy,) and they knew not what to answer him. And he came the third time, and said to them, "Sleep you now, and take your rest. It is enough: the hour is come: behold the Son of man shall be betrayed into the hands of sinners. Rise up, let us go. Behold, he that will betray me is at hand." And while he was yet speaking, came Judas Iscariot, one of the twelve: and with him a great multitude with swords and staves, from the chief priests and the scribes and the ancients. [Mark 14:32-43]

And going out, he went, according to his custom, to the mount of Olives. And his disciples also followed him. And when he was come to the place, he said to them, "Pray, lest you enter into temptation." And he was withdrawn away from them a stone's cast; and kneeling down, he prayed, saying, "Father, if you will, remove this chalice from me: but yet not my will, but yours be done." And there appeared to him an angel from heaven, strengthening him. And being in an agony, he prayed the longer. And his sweat became as drops of blood, trickling down upon the ground. And when he rose up from prayer, and was come to his disciples, he found them sleeping for sorrow. And he said to them, "Why sleep you? Arise, pray, lest you enter into temptation." As he was yet speaking, behold a multitude; and he that was called Judas, one of the twelve, went before them, and drew near to Jesus, for to kiss him. [Luke 22:39-47]

3 

When Jesus had said these things, he went forth with his disciples over the brook Cedron, where there was a garden, into which he entered with his disciples.  And Judas also, who betrayed him, knew the place; because Jesus had often resorted there together with his disciples.  Judas therefore having received a band of soldiers and servants from the chief priests and the Pharisees, came there with lanterns and torches and weapons.  [John 18:1-3]

But what about this is mysterious. What man, waiting to be betrayed by a close friend, rejected by his countrymen, tortured and executed by jeering foreigners, wouldn't be sorrowful unto death?

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1. This is based on the division of the 15-decade Rosary into three groups of five decades. The three groups are the Five Joyful Mysteries  the Annunciation, the Visitation, the Nativity, the Presentation, and the Discovery in the Temple  the Five Sorrowful Mysteries  the Agony in the Garden, the Scouring at the Pillar, the Crowning with Thorns, the Laying on of the Cross, and the Crucifixion and Death  and the Five Glorious Mysteries  the Resurrection, the Ascension, the Descent of the Holy Spirit, the Assumption of Our Lady, and the Coronation of Our Lady. For more on the Rosary and its mysteries, see the  Rosary Center, the website of the Confraternity of the Holy Rosary.
2. All Scriptural quotations are taken from the Douay-Rheims Bible, with minor modernization of punctuation and word choice.
3. See, for example, the words from the Cross in John vs. the Synoptics.