Jesus’ Journey To Jerusalem

Title: Jesus' Journey To Jerusalem

Bible Book: Matthew 20 : 17-19

Author: David E. Owen

Subject: Easter; Palm Sunday; Cross



During the five years that I was in evangelism, I made a lot of journeys. In fact, I probably traveled well over 150,000 miles during those years. But one of the longest trips that I ever made only took about three hours. It was the winter of 1987, and a heavy snowstorm had come in. At that time, I was still living at home with my parents and driving to Bible college each day from Brevard, North Carolina to Greenville, South Carolina. Angie and I had been dating for several months, but she lived on campus at the school. So when the snowstorm came in, I decided (against my parents’ better judgment) to drive down a winding mountain road in the snow to retrieve my sweetheart and bring her back up that same winding mountain road in that same snow to my parents’ house. At least that way, we could spend time together during the three or four days that we were to be snowbound. Now, why in the world would I hazard my life in making such a perilous journey? Because I loved her, that’s why!

The “Via Dolorosa” means the “way of sorrows,” or it is sometimes called the “Via Crucis” meaning the “way of the cross.” Both of these terms refer to a stretch of road between the Praetorium Hall, where Jesus was brought before Pilate, and Golgotha. It was along this route that Jesus Christ walked, bowed under the weight of the cross.[1] Probably about two weeks before Christ walked the gauntlet down the Via Dolorosa, He was walking down the Jericho road. “And,” as our text says, “Jesus going up to Jerusalem took the twelve disciples apart in the way, and said unto them, Behold, we go up to Jerusalem; and the Son of man shall be betrayed unto the chief priests and unto the scribes, and they shall condemn Him to death, And shall deliver Him to the Gentiles to mock, and to scourge, and to crucify Him” (Matthew 20:17-19). Now, why in the world would Jesus hazard His life in making such a perilous journey? Because He loved us, that’s why!

This morning, as we again “tell the old, old story of Jesus and His love,”[2] it would be impossible to deal with all of the aspects of the Easter events in a single sermon, however, Jesus does present a summarized statement of what would take place as He anticipated His Jerusalem journey. He begins His statement in Matthew 20:18 with the word “Behold.” So that’s what I want us to do this morning – Behold His journey to Jerusalem.

I. Let’s Behold The Place Of This Journey

Jesus said, “Behold, we go up to Jerusalem” (Matthew 20:18). He, and no doubt his disciples, had been there many times. In fact, Jesus had gone at this same time every year since He was born. We know that because Luke tells us, “His parents went to Jerusalem every year at the feast of the passover” (Luke 2:41). This city, which is mentioned over 800 times in the Bible, was an important place in the mind of every Jew, for if Israel was the fatherland – Jerusalem was the mother city. As Paul said in Galatians 4:26, “Jerusalem which is above is free, which is the mother of us all.” As we think about this place, let’s notice that...

A. Jerusalem Was A City Of Prophecy.

Jesus had been going to Jerusalem every year to celebrate the Passover, but this time, this trip was not just a probability – it was a certainty. Nearly a year before this “began Jesus to show unto his disciples, how that he must go unto Jerusalem, and suffer many things of the elders and chief priests and scribes, and be killed, and be raised again the third day” (Matthew 16:21). But prophecy was an ignored truth as all of these events unfolded, “For,” as Acts 13:27 says, “they that dwell at Jerusalem, and their rulers... knew Him not, nor yet the voices of the prophets which are read every sabbath day.” Whether the inhabitants of Jerusalem realized it or not, prophecy was being fulfilled there. Luke’s record of Jesus’ statement reads, “Behold, we go up to Jerusalem, and all things that are written by the prophets concerning the Son of man shall be accomplished” (Luke 18:31). This was no accident or misfortune that would befall Jesus in Jerusalem. By no means! Jerusalem was an intentional target in the plan of God, for “when the time was come that He should be received up, He stedfastly set His face to go to Jerusalem” (Luke 9:51).

B. Jerusalem Was A City Of Peace.

The name Jerusalem means “founded in peace,” but peace is certainly not the characteristic that comes to mind when we think of this ancient city. Century after century, Jerusalem has been surrounded by wars and rumors of wars. It’s no wonder the psalmist said, “Pray for the peace of Jerusalem” (Psalms 122:6). This has historically and consistently been the city where peace was avoided. And even as we think about Jesus’ journey to Jerusalem, we know that He was coming there to fight the battle of the ages. The Bible says in Matthew 21:10, that when Jesus “was come into Jerusalem, all the city was moved, saying, Who is this?” The word “moved” means agitated. Most of Jerusalem sensed no peace in His coming there. But He came, not as a vicious warmonger or cruel warlord, but as “The Prince of peace” (Isaiah 9:6). And as Jesus ultimately “made peace through the blood of His cross” (Colossians 1:20), Jerusalem became the city where peace was achieved.

C. Jerusalem Was A City Of Passion.

Please understand that Mel Gibson didn’t coin the term “passion.” This is a good Biblical term used in Acts 1:3, which says, “To whom also He showed himself alive after His passion by many infallible proofs, being seen of them forty days, and speaking of the things pertaining to the kingdom of God.” The term “passion refers to “the sufferings of Jesus in the period following the Last Supper and including the Crucifixion.”[3] The people of Jerusalem were the observers of His passion. “They gaped upon (Him) with their mouths” (Psalms 22:13). Matthew tells us that the Roman soldiers “crucified Him... and sitting down they watched Him there” (Matthew 27:35-36). Luke tells us that “the people stood beholding” (Luke 23:35). Before the Last Supper, before the trial, before Calvary – Jesus looked out over the city and said, “O Jerusalem, Jerusalem, thou that killest the prophets, and stonest them which are sent unto thee, how often would I have gathered thy children together, even as a hen gathereth her chickens under her wings, and ye would not!” (Matthew 23:37). Even as they were hating Him, He was loving them, and in a very real sense, the people of Jerusalem were included as the object of His passion.

II. Let’s Behold The People On This Journey

Sometimes it’s nice to have someone with you when you’re making a long journey. As Jesus took His journey towards Jerusalem, He did not travel alone. “Behold,” He said, “we go up to Jerusalem” (Matthew 20:18). Who is included in this word “we”? Who were the people in this group that was making its way to Jerusalem? We notice that...

A. The Students Of Messiah Were On This Journey.

Matthew 20:17 says, “And Jesus going up to Jerusalem took the twelve disciples.” It seems evident that there were many sects, and schisms, and schools in Jerusalem and the surrounding region in Jesus’ day; and each one had it own leader or teacher who would find a following, and these followers were called “disciples.” But to be a follower and disciple of the Lord Jesus Christ was a special privilege – spiritually speaking, it was as if His disciples were enjoying the first-class seats. Each of His disciples had embarked upon their journey with Jesus from different walks of life – from fishing boats, from the receipt of custom, from other groups. These twelve men traveled with Jesus to Galilee, to Bethany, to Jericho, and even on this journey to Jerusalem. But as Jesus came closer and closer to Calvary, He said to Simon Peter, “Whither I go, thou canst not follow me now; but thou shalt follow me afterwards” (John 13:36). His disciples would be excluded from the final stage of Jesus’ journey that led to Golgotha.

B. The Servant Of Mischief Was On This Journey.

Jesus said, “Behold, we go up to Jerusalem; and the Son of man shall be betrayed unto the chief priests” (Matthew 20:18). They had an enemy agent on board, and the betrayer’s name was Judas. Matthew 26:16 tells us that after Judas went to the chief priests and made his devilish deal, “from that time he sought opportunity to betray Him.” In anticipating the betrayal, Jesus said, “woe unto that man by whom the Son of man is betrayed! It had been good for that man if he had not been born” (Matthew 26:24). What a sad destination Judas had come to. After Jesus was delivered to Pontius Pilate the Bible says, “Then Judas, which had betrayed him, when he saw that he was condemned” ultimately “went and hanged himself” (Matthew 27:3-5). Out of the twelve travelers who accompanied Jesus, He said, “none of them is lost, but the son of perdition” (John 17:12). And do we not have a similar dilemma in our company here this morning? All of you are in the right place, and from all visible indications you seem to be on the right track, but in reality some of you are just as lost as Judas was.

C. The Son Of Man Was On This Journey.

When Jesus said, “we go up to Jerusalem; and the Son of man shall be betrayed” (Matthew 20:18), was He speaking of some unknown third party? In John 12:34, “The people” said, “Who is this Son of man?” Let’s consider the identity of the Son of man. Actually, “Son of man” was one of the titles that Jesus used to refer to Himself. According to the International Standard Bible Encyclopaedia, “In Matthew it occurs over 30 times, in Mark 15 times, in Luke 25 times, and in John a dozen times.” As we are confronted with this title that Jesus embraced for Himself, we must also consider the indication of the Son of man. What does this title really mean? In some respects, it is a veiled Messianic title perhaps drawn from Daniel 7:13; one that many would not be familiar with. But as J. Sidlow Baxter reminds us, “As Son of Man He comes to share and sympathize.” Again, the ISB Encyclopaedia says that this title “gave expression to His sense of connection with all men in sympathy, fortunes and destiny.” By using this title here in our text, He is further connecting Himself with the human condition of suffering.

III. Let’s Behold The Purpose Of This Journey

At this juncture, we want to ask the question again. Knowing that He would be betrayed, and condemned to death, and delivered to the Gentiles “to mock, and to scourge, and to crucify Him,” why would He “go up to Jerusalem”? One songwriter put it like this, “Why did He go to Calvary; Why was His life’s blood shed for me; Why did He suffer as no man has ever done? There’s just one reason; I am the one.” His journey to Jerusalem was not intended for relaxation or recreation. This was not a vacation venture, but it was a pilgrimage of purpose.

A. His Purpose Included The Religious Condemnation.

He said that the chief priests and scribes “shall condemn Him to death” (Matthew 20:18). Let’s slip into the courtroom in Matthew 26 and get a glimpse of what is going on at this trial. Notice first that we hear the voice of the Judge at this trial. Caiaphas, the high priest said to Jesus, “I adjure thee by the living God, that thou tell us whether thou be the Christ, the Son of God” (Matthew 26:63). The word “adjure” means to take an oath. Caiaphas was trying to swear Jesus in as a witness for the prosecution. But Jesus wasn’t a witness or the defendant; He was Himself the Judge and He said, “Hereafter shall ye see the Son of man sitting on the right hand of power, and coming in the clouds of heaven” (Matthew 26:64). Nevertheless, we hear the verdict of the jury at this trial. And as Mark 14:64 says, “they all condemned Him to be guilty of death.”

B. His Purpose Included The Roman Crucifixion.

Paul said, “the preaching of the cross is to them that perish foolishness” (1 Corinthians 1:18). He also mentioned “the offence of the cross” in Galatians 5:11. For Jesus to be delivered to the Gentiles “to mock, and to scourge, and to crucify him” (Matthew 20:19), was an offensive thing. And for us to reiterate it year after year seems like a foolish and offensive thing from the world’s standpoint. As we preach this message of the crucified Christ, we realize that Jesus didn’t enjoy being crucified. On the contrary, He “endured the cross, despising the shame” (Hebrews 12:2), but it was part of the Divine purpose and plan. As we consider the mocking and scourging and crucifixion, we see the obedience of the cross, for Jesus, “being found in fashion as a man, He humbled Himself, and became obedient unto death, even the death of the cross” (Philippians 2:8).

C. His Purpose Included The Resurrection Conquest.

“Lo in the grave He lay; Jesus my Savior; waiting the coming day; Jesus my Lord.” His purpose was not to be conquered, but to conquer. So, “up from the grave He arose with a mighty triumph o’er His foes!” He had declared His anticipated victory over death by saying that “on the third day” the Son of man “shall rise again” (Matthew 20:19). “O death, where is thy sting? O grave, where is thy victory?” (1 Corinthians 15:55). “I am He that liveth, and was dead; and, behold, I am alive for evermore, Amen; and have the keys of hell and of death” (Revelation 1:18). In Isaiah 28:18 there is a statement of judgment that God makes against the drunkards of Ephraim, but I would like to use it as if Jesus were speaking to that one who held the keys of death and hell. As He came out of the grave, Jesus might have said to that powerless key holder, “Your covenant with death shall be disannulled, and your agreement with hell shall not stand.” Mark 16:2 reports that “Very early in the morning the first day of the week,” the women who intended to anoint the body of Jesus with spices “came unto the sepulchre at the rising of the sun.” They soon realized that the Son had already risen. As the angel said to them, “Ye seek Jesus of Nazareth, which was crucified: He is risen; He is not here” (Mark 16:6). He had demonstrated His awesome victory over death.


Can I use a phrase that the world might use, and say about this journey of Jesus to Jerusalem: “What a trip!” This journey of jeopardy became a journey of joy and a journey of justification and redemption. And dear friend, because He made that journey to the old city of Jerusalem in order to die, He made it possible for you and me to take a journey someday to the New Jerusalem in order to live.

Whether you say, “This train is bound for glory” or whether you say, “I’m gonna’ take a trip on the good ole’ gospel ship” – either way, God’s children are taking a journey. And if you have trusted in what Jesus accomplished at Jerusalem, then you can go too! “Come and go with me to my Father’s house; Where there’s joy, joy, joy – wondrous joy!”

[1] The “Via Dolorosa” as described at

[2] From the song “I Love To Tell The Story” – word by A. Katherine Hankey and music by William G. Fischer

[3] The American Heritage Dictionary


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