The following explanation of the Sorrowful Mysteries is taken from the October 16, 2002 apostolic letter The Rosary of the Virgin Mary (Rosarium Virginis Mariae) by Pope John Paul II.
THE SORROWFUL MYSTERIES
The Gospels give great prominence to the sorrowful mysteries of Christ. From the beginning Christian piety, especially during the Lenten devotion of the Way of the Cross, has focused on the individual moments of the Passion, realizing that here is found the culmination of the revelation of God’s love and the source of our salvation. The Rosary selects certain moments from the Passion, inviting the faithful to contemplate them in their hearts and to relive them. The sequence of meditations begins with Gethsemane, where Christ experiences a moment of great anguish before the will of the Father, against which the weakness of the flesh would be tempted to rebel. There Jesus encounters all the temptations and confronts all the sins of humanity, in order to say to the Father: “Not my will but yours be done” (Lk 22:42 and parallels). This “Yes” of Christ reverses the “No” of our first parents in the Garden of Eden. And the cost of this faithfulness to the Father’s will is made clear in the following mysteries; by his scourging, his crowning with thorns, his carrying the Cross and his death on the Cross, the Lord is cast into the most abject suffering: Ecce homo!
This abject suffering reveals not only the love of God but also the meaning of the man himself.
Ecce homo: the meaning, origin, and fulfillment of man is to be found in Christ, the God who humbles himself out of love “even unto death, death on a cross” (Phil 2:8). The sorrowful mysteries help the believer to relive the death of Jesus, to stand at the foot of the Cross beside Mary, to enter with her into the depths of God’s love for man and to experience all its life-giving power.
Prayed on: Tuesdays and Fridays; optional on Sundays during Lent
The Agony in the Garden
And being in an agony he prayed more earnestly; and his sweat became like great drops of blood falling down upon the ground. And when he rose from prayer, he came to the disciples and found them sleeping for sorrow, and he said to them, “Why do you sleep? Rise and pray that you may not enter into temptation.”
Fruit of the Mystery: Sorrow for Sin
The Scourging at the Pillar
Then Pilate took Jesus and scourged him.
Fruit of the Mystery: Purity
The Crowning with Thorns
And they stripped him and put a scarlet robe upon him, and plaiting a crown of thorns they put it on his head, and put a reed in his right hand. And kneeling before him they mocked him, saying, “Hail, King of the Jews!”
Fruit of the Mystery: Courage
Jesus Takes Up His Cross
So they took Jesus, and he went out, bearing his own cross, to the place called the place of the skull, which is called in Hebrew Golgotha.
Fruit of the Mystery: Patience
Then Jesus, crying with a loud voice, said, “Father, into your hands I commit my spirit!” And having said this he breathed his last.
Fruit of the Mystery: Perseverance