Jesus On His Way To The Cross

Jesus On His Way To The Cross

Introduction (Matthew 27:31–32; Luke 23:26–32):
As Jesus made His way to Golgotha, the events surrounding Judas, the crowds, and the prophecy of destruction remind us that God’s Word is certain. We must learn from both the worldly sorrow of Judas and the godly sorrow of Peter.

Judas’ Remorse and the Field of Blood
Matthew 27 tells us Judas was “remorseful” after seeing Jesus condemned. He returned the thirty pieces of silver, confessing, “I have sinned by betraying innocent blood.” Yet this sorrow did not lead to repentance. Judas experienced worldly sorrow, which brings death, while Peter—though guilty of denying Jesus—was filled with godly sorrow that brought repentance (2 Corinthians 7:10). These two men illustrate the eternal difference between worldly grief and true repentance.

Judas admitted Jesus’ innocence. After three years of witnessing His miracles, hearing His teaching, and observing His perfect character, Judas knew the truth. Yet instead of turning back to God, he hanged himself. Acts 1 records how Judas’ death fulfilled prophecy: his body burst open, and the field became known as the “Field of Blood.” This tied directly to prophecies in Zechariah 11:12–13, where thirty pieces of silver are thrown into the house of the Lord and used for the potter’s field. Even the priests, by refusing to put the money into the treasury, admitted Jesus was innocent—calling it “blood money.”

Simon of Cyrene and the Weight of the Cross
From Matthew 27 and Luke 23 we see Simon of Cyrene compelled to carry Jesus’ cross. The Lord had been scourged, beaten, mocked, deprived of sleep, and had already lost much blood. The weight of the crossbeam was too much for His weakened body. Simon’s unexpected service foreshadows what Jesus said: “Whoever does not bear his cross and come after Me cannot be My disciple” (Luke 14:27).

The Daughters of Jerusalem
As crowds and mourning women followed Him, Jesus turned and said, “Do not weep for Me, but weep for yourselves and for your children” (Luke 23:28). His agony would soon end, but theirs would come in the destruction of Jerusalem. Within forty years, the Roman armies surrounded and leveled the city, fulfilling His prophecies in Matthew 24 and Luke 19:41–44. Josephus records the horror of that siege—over a million dead, families torn apart, starvation, and slaughter. Jesus, even in His suffering, wept for Jerusalem’s rejection of God’s Son.

Prophecies of Mourning and Judgment
Zechariah 12:10–14 foretold a day when Jerusalem would mourn over “the one they pierced.” This was fulfilled in Christ’s crucifixion and in the judgment that followed. God’s Word shows us how rebellion against Him always leads to destruction. Yet those who believe and obey find life.

Jesus On His Way To The Cross Sermon Outline:

• Introduction (Matthew 27:31–32; Luke 23:26–32)

  • Jesus’ journey to Golgotha connects prophecy, sin, and salvation.

• Judas’ Remorse and the Field of Blood

  • Matthew 27:3–10 – Judas’ remorse but no repentance.

  • 2 Corinthians 7:10 – Godly sorrow vs worldly sorrow.

  • Acts 1:16–20 – Judas’ death fulfills prophecy.

  • Zechariah 11:12–13 – Thirty pieces of silver and the potter’s field.

• Simon of Cyrene and the Cross

  • Matthew 27:32; Luke 23:26 – Simon compelled to carry the cross.

  • Jesus’ weakened condition from scourging.

  • Luke 14:27 – Call for discipleship by bearing our cross.

• The Daughters of Jerusalem

  • Luke 23:27–31 – Women weep for Jesus.

  • Jesus directs their sorrow toward themselves and their children.

  • Matthew 24:19–21; Luke 19:41–44 – Prophecy of Jerusalem’s destruction.

• Prophecies of Mourning and Judgment

  • Zechariah 12:10–14 – Mourning over the pierced one.

  • Fulfilled in Christ’s crucifixion and Jerusalem’s fall.

  • Lesson: rejecting God’s Son brings destruction; repentance brings life.

Call to Action
The cross confronts us with a choice. Judas chose worldly sorrow and perished. Peter chose godly sorrow and was restored. Which will you choose? Jesus bore His cross for us—will you take up yours and follow Him? Repentance, obedience, and faith lead to eternal life.

Key Takeaways

• Judas’ remorse (Matthew 27:3–10) teaches the danger of worldly sorrow.

• Godly sorrow (2 Corinthians 7:10) leads to repentance and forgiveness.

• Prophecy of thirty silver pieces fulfilled (Zechariah 11:12–13).

• Simon of Cyrene illustrates bearing the cross (Luke 14:27).

• Jesus warned of Jerusalem’s destruction (Luke 23:27–31; Matthew 24:19).

• Prophecy of mourning over the pierced one fulfilled in Christ (Zechariah 12:10–14).

Scripture Reference List

• Matthew 27:3–10 – Judas’ remorse and the thirty pieces of silver.

• 2 Corinthians 7:10 – Godly sorrow brings repentance.

• Acts 1:16–20 – Fulfillment of prophecy in Judas’ death.

• Zechariah 11:12–13 – Thirty pieces of silver and the potter’s field.

• Matthew 27:31–32; Luke 23:26 – Simon carries the cross.

• Luke 14:27 – Call to discipleship.

• Luke 23:27–31 – Daughters of Jerusalem warned.

• Matthew 24:19–21 – Prophecy of Jerusalem’s destruction.

• Luke 19:41–44 – Jesus weeps over Jerusalem.

• Zechariah 12:10–14 – Mourning over the pierced one.

Prepared by Bobby Stafford of the church of Christ at Granby, MO