Introduction:

I. Judas’ Wrong Repentance

Contrary to rabbinical law, the first two phases of Jesus’ religious trial were carried out during the night and away from the Temple. He had first been brought before the former high priest Annas, probably in the hope that this wicked conniver could concoct a charge against Jesus that would justify the death penalty.  When that failed, Christ was brought before the acting high priest, Caiaphas, and the hastily-assembled Sanhedrin. Even with willing false witnesses that group was also unable to indict Jesus. Only when He confessed to being the Christ and God’s Son did they discover a way to destroy Him. Although He spoke the truth, they convicted Him of blasphemy and being worthy of death (Matt. 26:63–66).

"But Jesus kept silent. And the high priest said to Him, “I adjure You by the living God, that You tell us whether You are the Christ, the Son of God.” Jesus *said to him, “You have said it yourself; nevertheless I tell you, hereafter you will see the Son of Man sitting at the right hand of Power, and coming on the clouds of heaven.” Then the high priest tore his robes and said, “He has blasphemed! What further need do we have of witnesses? Behold, you have now heard the blasphemy; what do you think?” They answered, “He deserves death!”" (Matthew 26:63-66, NASB95)

He was sentenced to death for the truth, for being who He indeed is.

A.            Two Contrasts (Matthew 27:1-5)

1.            Between the Wicked Leaders and the Sinless Christ (v.1-2)

a)            The Religious Leaders had two hurdles to cross.

(1)          They Had To Plan A Way To Make Their Decision Appear Legal Under Rabbinical Law. Mark mentions that in addition to all the chief priests and the elders, “scribes, and the whole Council” were present (15:1).

(2)          Because the people knew that all trials involving the death penalty had to be conducted in the daytime and in the Temple court, they had to wait until morning of that Passover Friday to reconvene the Sanhedrin in its legitimate council chamber (Luke 22:66). The counsel they took among themselves amounted to reasserting the charges against Jesus and reaffirming the verdict to put Him to death (Luke 22:67–71). 

(3)           After that point, however, the Jewish leaders dropped all pretense of legality.

(a)           Rabbinical law required that a sentence of death could not be carried out until the third day after it was rendered and that during the intervening day the members of the court were to fast.

(b)           The delay of execution provided additional time for evidence or testimony to be discovered in the defendant’s behalf. Because Friday was a holy day for Judean Jews, which included virtually all the religious leaders, and the next day was the Sabbath, the earliest legitimate execution of Jesus could not have been until Sunday-assuming the trial itself had been legitimate.

(c)           On this occasion, however, the Sanhedrin did not comply with that requirement. Now that Jesus was finally in their custody, they determined to destroy Him as quickly as possible.

(d)           But because they were not allowed to administer the death penalty themselves (John 18:31), the Jewish leaders now had to convince the Roman governor to give immediately the required permission for Jesus’ execution. Therefore they bound Him, and led Him away, and delivered Him up to Pilate the governor. With that hearing, the first phase of Jesus’ secular, Roman trial would begin.

(4)           Pontius Pilate had been the Roman governor of Judea since a.d. 26, when Tiberius Caesar was emperor, and continued to govern until the year 36. Jesus was taken to the Praetorium, the official provincial residence of the governor, and to keep from being ceremonially defiled and thereby prevented from celebrating the Passover later that day, the Jewish leaders waited outside (John 18:28).

2.            Between Judas and Innocent Jesus (v.3-5).

a)            Judas saw that Jesus was condemned (v.3).

Judas had fulfilled his usefulness to the chief priests and elders and they wanted nothing more to do with him. He was now a rejected outcast-to them, to the disciples, and to Jewish society in general.  Even before dawn it had became obvious to Judas and the others in the courtyard that the foregone verdict of the Jewish leaders had been confirmed.  

(1)          Although (saw) was sometimes used in the figurative sense of being aware of or perceiving, its use here suggests literal, physical sight.  If Peter was able to see Jesus during at least part of the trial (Luke 22:61), then others in the courtyard could have seen Him as well. Judas had seen Jesus maligned, spat upon, beaten, and mocked. Now he watched in bewilderment as his condemned Teacher was taken to Pilate.

(2)           As Judas watched Jesus being carried away to Pilate, the full enormity of his treachery finally began to dawn on him as he realized the Jewish leaders did indeed intend to put Jesus to death.  It was seeing Jesus so unjustly condemned that caused Judas to do what he now did.

(a)           He knew Christ, how good Christ was. He did not believe Jesus to be the Messiah, but he knew that Jesus was a tremendously good man, and Judas knew that it was because of his sin that Jesus was being condemned to death in a most unjust way.  This fact—plus the fact that Jesus was definitely God’s Son and that God was causing a sharp pang of guilt in the chest of Judas—drove Judas to seek relief. He felt boiling up within him an intense remorse and grief, the sense of being all alone, even without God, and a sense of not knowing what to do. It was too much, more than he could bear.

(b)           The one last obstacle was the permission of Pilate, which Judas had no reason to believe would be denied. Once Pilate consented, Jesus’ death would be inevitable.

b)            Judas Felt Remorseful (v.3)

(1)          He Began To Experience Intense Guilt.  Judas’s remorse was not repentance of sin. 

(a)           Matthew did not use metanoeo, which means a genuine change of mind and will, but metamelomai, which merely connotes sorrow or regret.  This word expresses the mere desire that what is done may be undone, but with no effective change of heart.  He did not experience spiritual penitence but only emotional remorse. Although he would not repent of his sin, he could not escape the reality of his guilt.

(b)           The Parable of the Two Sons (Matt. 21:28-32). 

(i)             Judas was more sorry for the result of his sin than for the sin itself. There is a huge difference in being sorry about your sin, and being sorry for your sin.

c)            What Is Repentance And How Does It Relate To Salvation?

The meaning of the word repentance has been twisted in recent years to the point that its biblical meaning is now obscured in the minds of many. The idea that genuine repentance could result in anything but a change of life is completely foreign to Scripture.  What does the Bible teach about the relationship between salvation and repentance?

(1)           It Teaches That Repentance Is Essential To Salvation. One cannot truly believe unless he repents, and one cannot truly repent unless he believes.  Repentance and faith are two sides of the same coin (but they are not synonymous terms). Acts 11:18 and 2 Peter 3:9 are two of the many verses that teach that repentance is necessary for salvation. Perhaps 2 Timothy 2:25 best sums up the relationship between repentance and saving faith when it speaks of "repentance to the acknowledging of the truth" (Acts 20:21).

(2)           It Is An Actual Turning From Sin.  The Greek word for repentance, metanoia, while it means "to have another mind," cannot properly be defined to exclude a sense of hatred of and penitence for sin. The biblical concept of repentance involves far more than merely a casual change of thinking. Biblically, a person who repents does not continue willfully in sin.  Repentance is a turning from sin, and it always results in changed behavior (Luke 3:8; 1Thess.1:9; Jonah 3:1-10; Matt.12:48). While sorrow from sin is not equivalent to repentance, it is certainly an element of scriptural repentance (2 Corinthians 7:10).

(3)           The Gospel Presentation.  Some say that salvation is only the granting of eternal life, not necessarily the freedom of a sinner from the bondage of his iniquity.  Telling people that God loves them and has a wonderful plan for their lives is only half the truth.  God hates sin and will punish unrepentant sinners with eternal torment.  No gospel presentation is complete if it avoids or conceals those facts.  Any message that fails to define and confront the severity of personal sin is a deficient gospel.  And any “salvation” that does not alter a lifestyle of sin and transform the heart of the sinner is not the salvation that God’s Word speaks of.

d)            Judas Felt Remorseful to the Chief Priest, not to God (v.3) 

(1)           Judas Needed To Turn To God. 

Sin Should Lead To Repentance.  When we sense guilt for real sin, we should repent and turn from the sin. But to whom we turn to is the critical factor: we are to turn to God. Turning away from sin is not enough. Changing and turning our backs and walking away from sin is not enough. We must turn our faces toward God and walk with Him.

“Therefore repent of this wickedness of yours, and pray the Lord that, if possible, the intention of your heart may be forgiven you." (Acts 8:22, NASB95)

"Let the wicked forsake his way And the unrighteous man his thoughts; And let him return to the Lord, And He will have compassion on him, And to our God, For He will abundantly pardon." (Isaiah 55:7, NASB95)

“But if the wicked man turns from all his sins which he has committed and observes all My statutes and practices justice and righteousness, he shall surely live; he shall not die." (Ezekiel 18:21, NASB95)

“Yet even now,” declares the Lord, “Return to Me with all your heart, And with fasting, weeping and mourning;" (Joel 2:12, NASB95)

e)            Judas Made Restitution (v.3)

(1)           Judas Was To Late. 

Judas did what God wants every man to do: make restitution for his sin.  But he was too late. He should have made restitution while events could be changed. He should have shown a repentance to God and returned the money before Christ was condemned.

(2)           We Should Make Restitution for Our Sins.      

We must act soon enough to make amends and to change events. The first step, of course, is to repent before God and then we can make restitution. But note, there is a right way and a wrong way to do both. Judas remorseful, but he repented in a wrong way. He turned in remorse to men instead of turning to God. He made restitution, but he made restitution too late. We must turn to God and make restitution, being sure to correct the situation before its to late. 

(3)           Obtaining Things Through Evil Ways Will Eat At You!

Money and other things which are secured through evil ways will eat away at a person’s mind and heart.  "Your gold and your silver have rusted; and their rust will be a witness against you and will consume your flesh like fire. It is in the last days that you have stored up your treasure!" (James 5:3, NASB95)

f)             Judas Confessed (v.4)

Confession is essential if we want forgiveness, but confession is to be made to God not to men.  Judas confessed, but he confessed to the priests not to God.  This prayer can serve as a pattern to the Christian when he is guilty of sin in his life today.

(1)           Confession Must Be Made To God (Psalm 51:4)

(a)           Only God can forgive sins (Matt.26:28; Mark 2:1-12 cf. Acts 5:31; Ez.10:11; Jer.3:13). 

(b)           David began his prayer freely admitting & confessing his sin (v.1-4)

(c)           Confession means “to say the same thing about sin as God does”

(d)           Honesty is vital; we must be true in our confession of sin.

(e)           Continual confession of sin is an indicator of genuine salvation.

(f)            This verb occurs more often in 1 John than in any other book (1:9; 4:2, 3, 15).

(2)           David & Judas Took Responsibility For Their Own Sin.

(a)           We sin and are personally responsible for our own sin. No one else is responsible for our sin. Blame cannot be laid at anyone else’s feet (Ezekiel 18:20).

"The one who sins is the one who dies. The child will not be punished for the parent’s sins, and the parent will not be punished for the child’s sins. Righteous people will be rewarded for their own goodness, and wicked people will be punished for their own wickedness." (Ezekiel 18:20, NLT)

(b)           Note something important: Judas accepted personal responsibility for his sin; he blamed no one else. He said, “I have sinned.” His problem was that he went to men instead of going to God.  Many in the Roman Catholic Church go to man instead of God. 

(3)           David Then Displays Real Sorrow Over His Sin (Psalm 51:17).

(a)           The main characteristic of true confession is godly sorrow produces repentance (2Cor.7:10).

(b)           God will forgive any repentant sinner who truly turns away from his sin and turns to God and confesses his sin.

(4)           David Asks God For Forgiveness (Psalm 51:1,7-9).

(a)           To forgive our sins means that God forgives the guilt of sin.  God counts the death of Jesus Christ as our punishment; Jesus bore our guilt of sin.

(b)           To cleanse us from all unrighteousness means that God cleanses us from all the dirt, filth, pollution, and contamination of sin.  Not a single spot or stain remains on us!

(c)           Cleansing Has Two Sides To It: The Positional & The Personal

(i)             The blood of Jesus Christ delivers us from the guilt of sin and gives us a right standing before God (justification).  God is able to forgive because Jesus’ death has satisfied His law.

(ii)            God is also interested in cleansing a sinner inwardly – “Create in me a clean heart”.  When our confession is sincere, God does cleansing work in our hearts by His Spirit.

(5)           The Blessedness Of Forgiveness (Psalm 32:1-5; Acts 3:19).

(a)           The glorious truth is that God has graciously provided for men what they could never obtain on their own. In Isaiah 43:25 God says, “I, even I, am the one who wipes out your transgressions for My own sake; and I will not remember your sins,” while in Isaiah 44:22 He adds, “I have wiped out your transgressions like a thick cloud, and your sins like a heavy mist” (cf. Num. 14:18; Pss. 65:3; 85:2; 86:5; 130:3–4).

(b)           There is only one way to receive God’s forgiveness—through faith in His Son Jesus Christ (Acts 5:31; 10:43; Eph.1:7; Col.3:14).

(c)           Don’t Wait Another Day (Acts 24:25).

"Behold, now is the accepted time; behold, now is the day of salvation." (2 Corinthians 6:2, NKJV)

3.            Judas Threw The Money At The Feet Of The Priests (Matt.27:5).

a)            This Was An Act Of Frustration And Anger, Of Hopelessness And Helplessness.

(1)           What could he do? The religionists were not going to change their verdict against Christ. Neither were they going to help him in his desperate need.

(2)           In his mind there was no one to help. He was stricken with guilt, standing all alone with no one to help. Hopelessness and helplessness set in.

(3)           In anger against the priests he threw the blood money into the court at the feet of the priests, and raced out of the temple into the streets of the city. He passed through the city gate into the country, seeking to escape his conscience.

b)            When Facing Spiritual Need, God Is The One To Whom We Should Turn, Not Man.

(1)           The help of man in providing spiritual deliverance is empty. The end result of man’s deliverance is always frustration, helplessness, and hopelessness. Man cannot erase guilt and liberate the anguished soul of man.

4.            Judas Fell Into Utter Despair And Hung Himself (Matt.27:5).

a)            His guilt was to much to bear.

(1)           He was gripped by guilt, grief, despair, and helplessness. He was haunted inside and saw no hope. Left alone with his thoughts, he felt his sin was too terrible to be forgiven. He felt God could never forgive him for so great a sin.

(a)           He felt his sin was too great to be forgiven.

(b)           He thought the mercy of God was limited, too small to forgive his sin.

(c)           He thought his sin was greater than the mercy of God.

(d)           He allowed his sin to overshadow and blot out the mercy of God.

“My soul loathes my life; I will give free course to my complaint, I will speak in the bitterness of my soul." (Job 10:1, NKJV)

"I sink in deep mire, Where there is no standing; I have come into deep waters, Where the floods overflow me." (Psalm 69:2, NKJV)

"When I thought how to understand this, It was too painful for me—" (Psalm 73:16, NKJV)

"But Zion said, “The Lord has forsaken me, And my Lord has forgotten me.”" (Isaiah 49:14, NKJV)

"that at that time you were without Christ, being aliens from the commonwealth of Israel and strangers from the covenants of promise, having no hope and without God in the world." (Ephesians 2:12, NKJV)

Thought 1. We should never abandon ourselves to despair nor become suffocated with grief. We should never be haunted with helplessness and hopelessness. Christ Jesus delivers and helps meet our need perfectly.

Thought 2. God’s mercy is so great and so sufficient it will cover any sin. We just need to come to Him, confess and repent, then He will forgive and deliver us unto eternal life.

Thought 3. Note the difference between Judas and Peter. Both sinned against the Lord and regretted their sinful acts, but only Peter repented. He repented and was received by the Lord and recommissioned for service (John 21:15-17). But Judas gave up in utter despair and destroyed himself. Regret can lead to repentance or to remorse and destruction.