Matthew 26:31-46 - Spiritually Aware
It is good to be with you this week. If you have your Bibles, open them to Matthew 26. We are continuing our series through Matthew, entering into our final mini-series that we are calling The Last Days. If I haven’t met you yet, my name is Brad. I’m one of the elders and the lead pastor here at The Well, and it is just a privilege to be with you in your living room, your car, on the treadmill, or wherever you’re hanging out watching home church. One of the advantages we’ve found with home church is that you can be just about anywhere and still stay connected.
We are continuing through Matthew in our typical fashion, teaching expositionally through a book of the Bible. Last week, Josh Holly, one of our campus pastors—who did a bang-up job handling the text—walked us through Jesus enjoying a final Passover meal with His disciples in the upper room. One observation he made that is especially worthy of note is that Jesus sent Peter and John to prepare the place for the Passover. Jesus was fully aware that Judas was His betrayer, so He kept the location under wraps until that night when Judas arrived with the others.
Jesus was only hours from His arrest. He gathered His disciples together and washed their feet, fully aware of the betrayer in their midst who had already set the plan in motion. During that meal, Jesus identified Judas, saying that the one who dipped his hand in the bowl with Him would betray Him. In John’s Gospel, Jesus dips the morsel and hands it to Judas, saying, “The one I’m handing this to is the betrayer.” Judas was fully exposed in that moment and promptly exited the meal. Jesus then finished the Passover meal and transformed its meaning—shifting it from a Jewish sacrifice commemorating God’s deliverance of Israel from Egyptian slavery to a remembrance of the ultimate Lamb of God who takes away the sins of the world.
All throughout our passage this week, you are going to find a consistent pattern: the disciples are physically present, but spiritually unaware. They are in the room where it happens, but completely blind to the spiritual reality.
Physically Present, Spiritually Unaware
We have seen this pattern before. If you think back to Matthew 17 and the Transfiguration, Jesus went up on the mountain and brought Peter, James, and John. He was transfigured before them in an incredible sight, with Moses and Elijah appearing on either side of Him. If you remember how that went down, Peter opened his mouth—which is usually a sign that something is about to go sideways. Peter opened his mouth and said, “Lord, it is good for us to be here! Let’s build three tents!” Talk about being physically present and spiritually unaware. Peter, just be quiet! You have no idea what you are experiencing, and you’re just running your mouth.
Matthew 17:1-8 (NASB)
Six days later Jesus took with Him Peter and James and John his brother, and led them up on a high mountain by themselves. And He was transfigured before them; and His face shone like the sun, and His garments became as white as light. And behold, Moses and Elijah appeared to them, talking with Him. Peter said to Jesus, ‘Lord, it is good for us to be here; if You wish, I will make three tabernacles here, one for You, and one for Moses, and one for Elijah.’ While he was still speaking, a bright cloud overshadowed them, and behold, a voice out of the cloud said, ‘This is My beloved Son, with whom I am well-pleased; listen to Him!’ When the disciples heard [this], they fell face down to the ground and were terrified. And Jesus came to [them] and touched them and said, ‘Get up, and do not be afraid.’ And lifting up their eyes, they saw no one except Jesus Himself alone.
That same dynamic is present in Matthew 26. To the disciples, what they just experienced in the upper room was simply another Passover meal—a tradition they had celebrated year after year. But for Jesus, this was His last meal. Jesus was looking at this moment the way someone looks at life when they know their death is imminent. He was lost in thought, looking toward the cross, His upcoming arrest, and His betrayal. His mind was focused on eternal realities.
Matthew 26:30 (NASB)
After singing a hymn, they went out to the Mount of Olives.
After singing a hymn, they went out to the Mount of Olives. When we hear geographical references in the Bible—like leaving the upper room and going to the Mount of Olives—we often miss the physical reality. If you look at the Temple Mount, the southern end is where Jesus would have walked after leaving the upper room. He walked along the southern wall and crossed the Kidron Valley below. Just on the eastern side of the Kidron Valley is the Mount of Olives.
What is fascinating about this route is that during Passover, thousands of lambs were being sacrificed at the temple. The blood of those sacrifices drained from the altar down the southeast side of the Temple Mount directly into the Kidron Valley. That means Jesus walked across the Kidron Valley, likely stepping over the drained blood of the Passover lambs, on His way to the garden as the true Lamb who was about to be sacrificed.
The Warning and Peter’s Boast
As they made their way, Jesus dropped a significant truth on them.
Matthew 26:31-32 (NASB)
Then Jesus said to them, ’You will all fall away because of Me this night, for it is written, ‘I WILL STRIKE DOWN THE SHEPHERD, AND THE SHEEP OF THE FLOCK SHALL BE SCATTERED.’ ‘But after I have been raised, I will go ahead of you to Galilee.’
Jesus told them plainly, “You will all fall away because of Me this night. For it is written: ‘I will strike down the shepherd, and the sheep of the flock will be scattered.’ But after I have been raised, I will go ahead of you to Galilee.” Jesus was quoting Zechariah 13:7.
Imagine that moment. You just had a wonderful feast with Jesus, complete with multiple courses and wine. You’re feeling close and connected, and as soon as you walk outside, Jesus says, “By the way, every single one of you is going to abandon Me tonight.” That was not what they wanted to hear, but it was absolute reality. And Jesus followed it with hope: “After it happens, I’ll see you in Galilee.”
Matthew 26:33 (NASB)
But Peter said to Him, ‘[Even] though all may fall away because of You, I will never fall away.’
Here comes Peter, running his mouth again: “Even though all may fall away because of You, I will never fall away.” Peter’s life is a case study in humility. If you are new to following Jesus, you need to understand that the destination for every disciple is humility. You can either humble yourself, or you can be humbled—either way, you end up at the same destination. Peter was a man who preferred the hard way. He was all passion and no polish. Remember, just an hour or two earlier, these disciples were arguing among themselves about which one of them was the greatest.
Matthew 26:34 (NASB)
Jesus said to him, ‘Truly I say to you that this [very] night, before a rooster crows, you will deny Me three times.’
Jesus looked at him and said, “Truly I say to you that this very night, before the rooster crows, you will deny Me three times.” Roosters are loud, they wake up early, and they are wickedly consistent. Jesus told Peter that before the morning alarm went off, he would deny Him three times.
It is worth noting how Jesus addresses Peter throughout the Gospels. In Matthew 16, Jesus changed his name from Simon to Peter, meaning “the Rock.” When Peter was operating in faith, Jesus called him Peter. But when Peter stepped out of line, Jesus addressed him by his old name. In Luke’s account of this night, Jesus said, “Simon, Simon, behold, Satan has demanded permission to sift you like wheat; but I have prayed for you, that your faith may not fail; and you, when once you have turned again, strengthen your brothers.”
Luke 22:31-32 (NASB)
‘Simon, Simon, behold, Satan has demanded [permission] to sift you like wheat; but I have prayed for you, that your faith may not fail; and you, when once you have turned again, strengthen your brothers.’
Peter was completely unaware of the spiritual warfare swirling around him. He was reacting emotionally to the moment with no comprehension of what God was doing.
Matthew 26:35 (NASB)
Peter said to Him, ‘Even if I have to die with You, I will not deny You.’ All the disciples said the same thing too.
Peter doubled down: “Even if I have to die with You, I will not deny You!” And all the disciples chimed in, “Me too! Me too!” They completely missed the point. They were physically present, but spiritually unaware. They had no concept of what Jesus was about to endure, nor what they themselves would soon face.
John 15:20 (NASB)
’Remember the word that I said to you, ‘A slave is not greater than his master.’ If they persecuted Me, they will also persecute you; if they kept My word, they will keep yours also.
Jesus had warned them in John 15:20 that if the world persecuted Him, it would persecute them too. The path ahead was suffering, yet they remained blind to it.
Entering Gethsemane: The Place of the Press
Matthew 26:36 (NASB)
Then Jesus came with them to a place called Gethsemane, and said to His disciples, ‘Sit here while I go over there and pray.’
Jesus arrived with them at a place called Gethsemane. The word Gethsemane literally means “the olive press.” The Garden of Gethsemane is an olive grove situated on the Mount of Olives. Throughout that area, archaeologists have found ancient caves containing stone presses used to crush olives to extract their oil. Jesus went to the place of pressing to have the weight of the sins of the world pressed upon Him.
From Gethsemane, you have a direct line of sight across the Kidron Valley to the Temple Mount. It is only about a fifteen-minute walk. Jesus could see the city; He could see what was coming.
Jesus told the majority of His disciples to sit and pray while He went further. Notice that for Jesus, prayer was not a last resort. He didn’t view prayer as “the least I can do.” He modeled for us that prayer must always be our first move. Why? Because prayer is where you find the Father. His natural instinct, His place of safety, security, hope, and affirmation was in the presence of God.
Throughout the Gospels, the disciples never asked Jesus to teach them how to perform miracles, cast out demons, or preach great sermons. What they asked Him was, “Lord, teach us to pray.” They saw the daily, intimate practice Jesus had with the Father, and they recognized that His spiritual power flowed out of that intimacy.
Matthew 26:37 (NASB)
And He took with Him Peter and the two sons of Zebedee, and began to be grieved and distressed.
Jesus took Peter, James, and John deeper into the garden, and He began to be grieved and distressed. Why was Jesus feeling such sorrow and anxiety? He was beginning to feel a weight that you and I cannot fully comprehend.
Think about the last time you sinned and had a mouthful of regret. Remember that heavy weight in your chest when you realized, “I knew better, and I did it anyway”? As David wrote in Psalm 32:3, when he kept silent about his sin, his bones wasted away within him. That is the crushing weight of your own individual sin.
What Jesus was experiencing in Gethsemane was the realization that He was about to carry the weight of all human sin. Jesus had never committed a single sin. He had lived in unbroken communion with the Father from all eternity. Now, He was staring down the barrel of bearing our collective guilt.
2 Corinthians 5:21 (NASB)
He made Him who knew no sin [to be] sin on our behalf, so that we might become the righteousness of God in Him.
God made Him who knew no sin to be sin on our behalf, that we might become the righteousness of God in Him.
Romans 3:25 (NASB)
whom God displayed publicly as a propitiation in His blood through faith. [This was] to demonstrate His righteousness, because in the forbearance of God He passed over the sins previously committed;
Romans 4:25 (NASB)
[He] who was delivered over because of our transgressions, and was raised because of our justification.
Romans 6:23 (NASB)
For the wages of sin is death, but the free gift of God is eternal life in Christ Jesus our Lord.
Jesus was delivered over for our transgressions. The wages of sin is death, and Jesus was preparing to take that death in our place.
The Agony and the Cup
Matthew 26:38 (NASB)
Then He said to them, ‘My soul is deeply grieved, to the point of death; remain here and keep watch with Me.’
Jesus told Peter, James, and John, “My soul is deeply grieved, to the point of death; remain here and keep watch with Me.” This passage underscores the complete humanity of Jesus. The waterline of grief was rising to His neck. He invited His closest friends into His pain: “Stay awake with Me. I need you right now. I am overwhelmed with sorrow.”
Yet the disciples remained physically present, but spiritually unaware.
Matthew 26:39 (NASB)
And He went a little beyond [them], and fell on His face and prayed, saying, ‘My Father, if it is possible, let this cup pass from Me; yet not as I will, but as You will.’
Jesus went a little beyond them, fell on His face, and prayed: “My Father, if it is possible, let this cup pass from Me; yet not as I will, but as You will.”
What was this cup? Throughout Scripture, the cup represents the righteous wrath of God against sin. All Jesus had ever known was the perfect love and oneness of the Father. On the cross, He would experience divine separation and judgment on our behalf. When He cried out on the cross, “My God, My God, why have You forsaken Me?” the full weight of our sin was placed upon Him, and the Father turned His back as the Son paid our penalty.
In the ancient Roman military, if a unit committed treason or severe insubordination, they would sometimes line the soldiers up and hand the first soldier a cup of hemlock poison. That soldier had a choice: he could take a small sip, get slightly sick, and pass the deadly cup down the line to his comrades, or he could show ultimate loyalty, take the hit for his brothers, and drink the entire cup down to the dregs.
Psalms 75:8 (NASB)
For a cup is in the hand of the LORD, and the wine foams; It is well mixed, and He pours out of this; Surely all the wicked of the earth must drain [and] drink down its dregs.
Psalm 75:8 says that in the hand of the Lord there is a cup of foaming wine, and the wicked of the earth must drink it down to the dregs. When Jesus stood in Gethsemane, He was not passing the cup to anyone else. He took the full cup of God’s wrath and drank it to the dregs so that we who were guilty could go free.
Luke tells us that in this moment of agony, an angel ministered to Him, and His sweat became like great drops of blood falling to the ground.
Luke 22:43-44 (NASB)
Now an angel from heaven appeared to Him, strengthening Him. And being in agony He was praying very fervently; and His sweat became like drops of blood, falling down upon the ground.
When was the last time you labored in prayer to the point of intense perspiration? For most of us, prayer is not our strongest spiritual muscle. We start praying, and within ninety seconds our mind wanders to our to-do list, our anxieties, or our schedule. But Jesus was completely vulnerable with the Father: “God, I am in agony. If there is an audible we can call, let’s call it. But if this is Your plan, I submit to Your will.”
The Sleeping Disciples
Matthew 26:40-41 (NASB)
And He came to the disciples and found them sleeping, and said to Peter, ’So, you [men] could not keep watch with Me for one hour? ‘Keep watching and praying that you may not enter into temptation; the spirit is willing, but the flesh is weak.’
Jesus returned to the disciples after an hour of intense prayer and found them asleep. He looked at Peter and said, “So, you men could not keep watch with Me for one hour? Keep watching and praying that you may not enter into temptation; the spirit is willing, but the flesh is weak.”
Jesus was in the battle of His life, and His inner circle was taking a nap. In His hour of deepest need, they were completely absent spiritually. Have you ever felt that kind of disappointment? You are going through agony, you count on someone to be there for you, and they just drift away. It feels like betrayal, abandonment, and profound loneliness.
Notice what Jesus did next. He didn’t throw a tantrum, and He didn’t put His ultimate worth and security in the hands of fallible human beings. He went back to the only One who is truly faithful.
Matthew 26:42 (NASB)
He went away again a second time and prayed, saying, ‘My Father, if this cannot pass away unless I drink it, Your will be done.’
Jesus went away a second time and prayed, “My Father, if this cannot pass away unless I drink it, Your will be done.” He submitted entirely to the Father’s sovereign plan.
John 5:30 (NASB)
’I can do nothing on My own initiative. As I hear, I judge; and My judgment is just, because I do not seek My own will, but the will of Him who sent Me.
Jesus had said in John 5 that He sought not His own will, but the will of the Father who sent Him. Now, with less than twelve hours before His death on the cross, He declared the exact same thing.
Matthew 26:43-44 (NASB)
Again He came and found them sleeping, for their eyes were heavy. And He left them again, and went away and prayed a third time, saying the same thing once more.
He returned to find them sleeping again because their eyes were heavy. This time, He didn’t even wake them up. He went back a third time and prayed the same words. By that third time of prayer, the anxiety and grief gave way to resolve, peace, and focus. Jesus knew He was fully loved by the sovereign Father. The plan was set, His role was clear, and He was ready.
That is what genuine prayer does: it anchors our identity and aligns our hearts with God’s purposes. When we pray, we don’t need to put on a religious show. We don’t need to adopt Elizabethan English or pretend we have it all together. God is omniscient; He already knows our mess, our anxiety, and our besetting sins. When we bring our genuine brokenness to Him, we move from being spiritually unaware to spiritually awake.
Psalms 131:2 (NASB)
Surely I have composed and quieted my soul; Like a weaned child [rests] against his mother, My soul is like a weaned child within me.
Psalm 131:2 says, “Surely I have composed and quieted my soul; like a weaned child rests against his mother, my soul is like a weaned child within me.” That is the picture of resting in the presence of our Creator—complete security, provision, and peace.
Many believers struggle to pray publicly because they rarely pray privately. We have developed strong intellectual muscles or service muscles, but we have skinny prayer legs. We need the discipline of the squat rack in our prayer lives to build real spiritual strength.
Get Up, Let Us Be Going
Matthew 26:45-46 (NASB)
Then He came to the disciples and said to them, ’Are you still sleeping and resting? Behold, the hour is at hand and the Son of Man is being betrayed into the hands of sinners. ‘Get up, let us be going; behold, the one who betrays Me is at hand!’
Jesus came to the disciples the third time and said, “Are you still sleeping and resting? Behold, the hour is at hand and the Son of Man is being betrayed into the hands of sinners. Get up, let us be going; behold, the one who betrays Me is at hand.”
Mark’s Gospel tells us the disciples were speechless with embarrassment. Strike one, strike two, strike three—they had completely missed the moment. They were physically present, but spiritually unaware.
As we look at Jesus as our model, consider these concluding observations:
First, when difficulty came, Jesus turned immediately to prayer. Prayer is the most life-giving, peace-granting, and securing practice we have. A daily habit of prayer keeps us spiritually aware of what God is doing around us.
Second, as Jesus deepened His communion with the Father, His dependence on human approval shrank. People are sinners; they will eventually let you down. Only God will never leave you nor forsake you.
Finally, prayer empowered Jesus to endure the cup of suffering set before Him. Whatever cup of difficulty, loss, or trial you are walking through right now, His cup was infinitely heavier. Jesus drank the cup of wrath so that we might drink the cup of blessing. He faced His cross through prayer, and He invites us to walk in that same spiritual awareness today.
Let us pray.
Father, thank You for the example of Jesus. Thank You for the honesty, raw emotion, and absolute submission we see in Gethsemane. Lord, if we have skinny prayer legs, give us the grace and courage to strengthen that muscle. Teach us to rest in Your presence like a child with its mother. Anchor our identity in Your love, and make us not only physically present in our lives, but spiritually aware of Your kingdom. We pray this in Jesus’ name, Amen.