The First Sorrowful Mystery of the Rosary, the Agony in the Garden:
Our Lord sweating blood so much it soaked his hair and beard. Our Lord in his humanity--like us in all things but sin--allowing Himself to experience the worst anxiety and terror, seeing every sin that would be committed by every person from the beginning until the end of time.
Imagine the pain and sorrow He felt seeing in His mind's eye His priests banalizing and desecrating His Divine Sacrifice, and later sexually abusing little boys in virtually every diocese. Or seeing some of those same clerics once sexually abuses by their own pastors or fathers.
Imagine how much His heart was wrenched witnessing 40 million++ babies being killed in the womb, the most innocent and defenseless. Imagine the sorrow He felt even for the abortionist, how they are possessed and tormented by the devil.
Imagine Our Lord looking square at each of our's most grave sins against Him and eachother. The acts of impurity, the unjust acts of anger, the neglect of prayer and penance.
The Second Sorrowful Mystery: the Scouring at the Pillar:
Isn't the most beautiful of men Our Lord Jesus Christ, reaching perfect physical and mental development at the age of 33? Lean, muscular, strong. A brilliant, eloquent, fearless Shepherd. Penetrating eyes, a paternal face, flowing golden Brown hair and beard.
Now imagine the first barbed hook grabbing onto the flesh of His back, as He hung at a pillar completely naked. One square inch of flesh at a time was ripped open, until his entire backside was mutilated. And then he was turned to the otherside. By the time the scourging was finished, His whole face, neck, shoulders, torso, and legs were butchered.
Now imagine if that happened to us, all the inordinate care we give our body. Imagine Paris Hilton or Brad Pitt mutilated head-to-toe to the point we couldn't recognize them. Every act of vanity slicing across Our Lord's body.
The Third Sorrowful Mystery, the Crowning with Thorns:
I think it was Venerable Anne Catherine Emmerich, who through her visions of the Passion, said Our Lord's greatest pain was the Crowning with Thorns. Because the mind is where sin originates, in our thoughts and acts of free will.
Think of the billions of worldly, egotistical, atheistic thoughts that get circulated on the internet everyday. All the hidden, angry messages that keep replaying in the back of our minds.
Mother Teresa disclosed she dealt for 50 years with a kind of depression, and she said that kind of suffering corresponds to Our Lord's Crowning with Thorns. She is not exactly the trads favorite saint, but that little lady understood suffering. There is nothing more painful than mental illness, and mental illness is an epidemic across the materialistic nations. Souls so disoriented from reality and their own individual identity, they would rather die.
The Fourth Sorrowful Mystery, Carrying the Cross to Calvary:
When there is a fast food restaurant on every corner, and in a society that expects everyone to be in a certain Tax Bracket to "be somebody," who would think that the path to happiness not only in the next life but in this life, would require each one of us to do what Christ did, to directly look at whatever Cross God gives us, thank Him for it's saving grace, embrace it, pick it up, and pull that sucker up the hill. To keep doing that, persevering to the end.
I think how Our Lord fell three times. He was so physically and mentally exhausted He couldn't physically bear the Cross. But we're supposed to bear our cross at all times, right? If we fall, doesn't that mean moral weakness? Its easy to be discouraged by my own weaknesses, or to be confused by my own failings. I sense I need to look deeper within to know when my weaknesses are sins or where they are just my human nature reaching it's own physical limits.
The Fifth Sorrowful Mystery: Jesus' Died on the Cross:
That Holy Cross now divided into thousands of Relics around the world. Miraculously rediscovered by Constantine's mother St. Helena. That Cross which at the time of Christ was considered the worst form of torture and capital punishment. But that Cross that became the New Altar for the New Sacrifice. If you trace a line from where Our Lord was crucified, it ran straight through the altar of the Jewish temple where the priests simultaneously offered the sacrifice of the lambs, literally facing in the direction of the Cross. But in the end, no animal sacrifice or act of mortal man could save mankind. Only God Himself could save mankind by becoming man and offering His life to the Father.
I've tried to imagine how three hours on the Cross atoned for millenia of human sin. How the trillions and trillions of sins, even the most venial meriting long, terrible penances in purgatory, were mystically placed on the shoulders of our dying Savior. I cant imagine that. That mystery of Faith must rank up there with the mysteries of the Incarnation, Transubstantiation, or Our Lady's Assumption into Heaven.