Skip to content

With the Transgressors

March 30 2025

Book: Luke

Scripture: Luke 22:24-38

Thank you for reading this sermon from Christ Fellowship. I hope and pray that this sermon will be a blessing of grace and truth to you. With that said, let me encourage you not to use this sermon as a replacement for your local church. Christ Jesus did not establish his Church simply for us to consume content. Instead, He calls us to be part of a real, covenant family. 

I don’t watch a lot of basketball, but I do love the final rounds of the NCAA Tournament… especially when there’s a team that makes it farther than expected. It didn’t happen this year.

But imagine a team like that, a lower seed, making it to the final four. After the game, the players are in the locker room listening to the coach give his post-game speech. He’s talking about teamwork and overcoming adversity. But in the corner, the two best players are arguing over which one of them deserves to be the MVP.

That’s a problem, right? That’s the setup for our text this morning. Jesus is finishing up the Passover meal with his closest disciples. He’s just finished giving them some important details about His mission. The Gospel of John tells us that His words are accompanied by a dramatic act of service. Jesus washes the feet of His own disciples.

And somewhere during this powerful moment, an argument starts:

24 A dispute also arose among them, as to which of them was to be regarded as the greatest.

This is utterly juvenile! How can they be so ignorant? How are they missing the significance of this moment? How are their hearts so clouded by pride and self-importance?

But Jesus remains patient with them, discerning their hearts and instructing them on leadership.

25 And he said to them, “The kings of the Gentiles exercise lordship over them, and those in authority over them are called benefactors.

Jesus here is shedding light on the self-serving nature of worldly leadership. Powerful leaders claim to be serving the people, but typically they use their power for selfish gain.

We would be foolish to doubt this, even in a Democratic Republic. According to Jesus, most of the people in public service are motivated by status, control, and money.

26 But not so with you. Rather, let the greatest among you become as the youngest, and the leader as one who serves.

Forget the benefits of leadership, Jesus says. Use your authority to benefit others. Jesus is redefining greatness by His own example.

27 For who is the greater, one who reclines at table or one who serves? Is it not the one who reclines at table? But I am among you as the one who serves.

The word for service is the word diakoneo. It’s the Greek word for someone who waits tables. Which one is greater? The one waiting tables or the one sitting at the table?

But by His own example, Jesus demonstrates servant-leadership. What’s the lesson? It’s that greatness is found in humility, not in power. Instead of “what can I get?” the question is “how can I use my position to help others?”

28 “You are those who have stayed with me in my trials,

29 and I assign to you, as my Father assigned to me, a kingdom,

30 that you may eat and drink at my table in my kingdom and sit on thrones judging the twelve tribes of Israel.

Notice that Jesus is telling them something remarkable. These young men are going to rule with Christ in the kingdom of God.

This is everything the disciples wanted to hear. But they don’t yet realize the path to this promise is paved with suffering.

31 “Simon, Simon, behold, Satan demanded to have you, that he might sift you like wheat,

I want you to imagine Jesus saying this to you. Jesus says his name twice. “Simon, Simon” … look at me, Simon. And I imagine there was a dramatic pause, as Jesus looks Simon in the eyes. The eyes of Jesus are full of tenderness and concern.

My greatest enemy is targeting you, Simon. He wants to violently shake you. He’s claiming a right to do it, like he did with Job… this is a chilling moment.

And I can imagine Simon Peter shaking in his boots, thinking to himself… “what did you say, Lord?” Please tell me you said no!

32 but I have prayed for you that your faith may not fail. And when you have turned again, strengthen your brothers.”

Thanks, Jesus. Thanks for praying. But this doesn’t sound good, does it? And the other disciples are perhaps thinking now that Peter is the one who is going to betray Jesus. And that is shocking, because Peter has been the most zealous and committed disciple in the room until now.

33 Peter said to him, “Lord, I am ready to go with you both to prison and to death.”

Peter is always the most self-confident, at least in words. He rejects the notion that He would ever turn on Jesus. But…

34 Jesus said, “I tell you, Peter, the rooster will not crow this day, until you deny three times that you know me.”

That’s a gut punch. But it’s honest, and it’s real. Jesus tells Peter plainly that he is going to fail. Satan is going to take advantage of Peter’s insecurity.

And we should pause here and consider the deeper lesson. Pride is always a cover for insecurity. It’s a smokescreen. Our self-confidence is usually a mask to hide what we really feel inside, which is weakness. Pride doesn’t make us strong. It makes us fragile. It makes us an easy target for the Devil.

Pride grows in the soil of fear, self-doubt, and the desire to be “enough.” It thrives on self-focus and comparison. The prideful person is constantly asking himself, “Am I better than him?”

In the Screwtape Letters, C.S. Lewis writes this:

“God wants to bring the man to a state of mind in which he could design the best cathedral in the world, and know it to be the best, and rejoice in the fact, without being any more (or less) glad at having done it than he would be if it had been done by another.”

In other words, he would be just as happy to see it built by someone else. And this is what the disciples fail to see. They should be happy the kingdom of God is coming, regardless of their own position in the kingdom.

But instead, they were arguing about which of them was the greatest. And what they don’t realize is that they were demonstrating exactly the sort of sin Jesus came to redeem them from.

That’s because their pride was a cover-up for deep spiritual poverty. God would rather us be honest with ourselves about our need. What did Peter need more than anything right now? He needed faith in Jesus. He needed Jesus to pray for him. But in this moment, Peter was focused on his own resolve instead of his need.

35 And he said to them, “When I sent you out with no moneybag or knapsack or sandals, did you lack anything?” They said, “Nothing.”

In other words, God met your needs. That’s the heart of the Gospel. You bring nothing to the table. Only God can meet your needs. Only God can prepare you for what comes next.
Only God can provide what is necessary for you to survive the attacks of the enemy.

You bring nothing into this relationship. That’s where humility starts to grow. I need nothing except what God can provide. But the hour has now arrived for the Son of Man to be glorified.

36 He said to them, “But now let the one who has a moneybag take it, and likewise a knapsack. And let the one who has no sword sell his cloak and buy one.

This is a strange command at first glance. In the middle of teaching the disciples about servant-leadership and humility, Jesus tells them to take up the means of worldly power. Get your money and buy a sword. And this is something they were eager to do. But why would Jesus say this?

Commentary on this verse is confusing, especially the part about the sword. But I think the next verse explains everything.

37 For I tell you that this Scripture must be fulfilled in me: ‘And he was numbered with the transgressors.’ For what is written about me has its fulfillment.”

Normally, when we read this verse, we think of Jesus being treated as a criminal. He’s going to be hung on a cross between two criminals.

But I think there’s a greater meaning here. The disciples are also “transgressors”. The Gospel of Luke consistently and repeatedly portrays the disciples as spiritually weak and confused, even faithless.

Even now, they misunderstand the mission.

38 And they said, “Look, Lord, here are two swords.” And he said to them, “It is enough.”

From everything Jesus told them, the disciples are focused on making sure they have enough swords. How much more obvious can Luke make this for us?

Jesus didn’t go to the cross to die only for the obviously wicked—He died for the religious, the close, the committed disciples… who still fail. Even those closest to Him are transgressors in need of His substitutionary atonement.

And so, my encouragement for us this morning is to let the cross expose our pride. Where in your life are you defending your ego instead of confessing your weakness? I do it daily. I am so quick to defend myself instead of considering the pain I might be causing other people by my words and actions. I did it last night!

We need to trade our self-confidence for Christ-dependence. Instead of resting in our promises to God, we need to be resting in His promises to us. Jesus is far less concerned with what we are going to do for Him and far more concerned with us believing what He has already done for us.

This is important, because it’s the only way true humility is produced. And humility is essential for the Christian life. A life of spiritual endurance, costly discipleship, and servant-leadership is only possible with a humble heart. Those things grow like fruit on the tree of humility.

Pride can produce an impressive tree with shallow roots. It looks great until it’s destroyed by drought or storms. The tree of humility may not be as impressive or as flashy, but it has deep roots.

And what did Jesus say to His disciples? Abide in me and you will bear much fruit.

What am I telling you? I’m telling you (and myself) to dig deep into your dependence on Christ. Dig deep into honest confession. Dig deep into selfless service of other people. Humble yourself and be raised up by the God who considered it a joy to be numbered among transgressors like us.