Jesus’ Worst Moment: The Canaanite Woman Encounter: Matthew 15:21-28

Chapter Three
Sermon Title: “Jesus’ Worst Moment”
Matthew 15:21–28
Scripture and Sermon
This morning we continue our series “A day in the life of Jesus” with a Scripture that in 29 years I have never preached from. And probably after we read it, you will understand why. Some would call it “Jesus’ Worst Moment!” I don’t know if I would go that far, but it certainly is worth investigating. So turn with me to Matthew 15:21-28.
21 Leaving that place, Jesus withdrew to the region of Tyre and Sidon. 22 A Canaanite woman from that vicinity came to him, crying out, “Lord, Son of David, have mercy on me! My daughter is demon-possessed and suffering terribly.” 23 Jesus did not answer a word. So his disciples came to him and urged him, “Send her away, for she keeps crying out after us.” 24 He answered, “I was sent only to the lost sheep of Israel.” 25 The woman came and knelt before him. “Lord, help me!” she said. 26 He replied, “It is not right to take the children’s bread and toss it to the dogs.” 27 “Yes it is, Lord,” she said. “Even the dogs eat the crumbs that fall from their master’s table.” 28 Then Jesus said to her, “Woman, you have great faith! Your request is granted.” And her daughter was healed at that moment.
It’s Andrew again! I am really grateful for this opportunity to share some of the greatest moments of my life. The feeding of the five thousand and Jesus walking on the water are so memorable. But as unforgettable as those moments were, this morning your pastor has asked me to talk about a day I wish I could forget. In fact, I am quite surprised Matthew put it in his gospel. It’s tough to talk about because usually Jesus is always the hero of the story. He is the one who saves the day. But in this story, which actually happened, I was there, a lady is the one who is the star of the show. So I am glad you are sitting down because this story is going to blow your mind and maybe even challenge some of your long held beliefs about Jesus.
Let me start by giving you the backstory and a couple of important truths. This incident occurred as Jesus was once again trying to retreat from the crowds and this time from the religious leaders who were questioning every move he made. The Pharisees in Jerusalem had sent their very best interrogators to follow us again and point out anything and everything we did wrong. Do you realize how annoying that is? Here is Jesus trying to help people better understand who God is and He has to keep on answering stupid questions from these guys who were up to no good. The most recent so-called controversy dealt with us disciples. Apparently we didn’t wash our hands before we ate which I guess was a big no no according to their traditions and laws. You could tell Jesus was getting tired of their constant badgering. He called them out on how the Pharisees would not take care of their parents in their old age but instead tell them that their money was devoted to God. We were like, “You, go, Jesus!” Needless to say, Jesus needed to get away and decided that the best place to go was to the one place the religious leaders wouldn’t follow him, Tyre and Sidon. This was a land of heathens, or Gentiles more nicely put. No well respected Pharisee would step foot in that area. Jesus was going to get away where He could teach us more about the kingdom of God and avoid the big crowds that were following Him.
And now for the important truths that I need to tell you before recounting this story. First, Jesus is the most godly person I have ever met. He allowed the Spirit to direct Him in all of his decisions. When He told us we were going to Tyre and Sidon, we knew it was because God had told Him that is where we should go. The second truth is that I never saw Jesus ever sin. He never cursed, never lied, never stole, never gossiped and never said a careless word. Jesus was perfect concerning the things of God, but He was also fully human. He got tired. He got hungry. He needed rest. He experienced everything that came with living in a human body. This is going to be very important to remember for what I am about to tell you.
So we get to this foreign area, which honestly none of us were very comfortable being there. And we are searching for a place to stay for the night as we enter the city. It was kind of nice because the crowd that had been following us stopped the moment we entered this Gentile land. They weren’t willing to follow Jesus here. And we were going to have some alone time with the Lord where He could teach us in more depth.
And so as we are walking down the road, here comes this crazy lady screaming at the top of her lungs, “Lord, Son of David, have mercy on me! My daughter is demon-possessed and suffering terribly.” And Jesus does something I had never seen Him do, He just keeps on walking. Well, the lady doesn’t get the hint. She keeps on screaming from behind as we continue down the road. “Lord, Son of David, have mercy on me! My daughter is demon-possessed and suffering terribly!” Now let me say here that I am kind of impressed with this woman. First, she is clearly a Canaanite lady, which means she doesn’t believe the way we do. Her people have been our enemies since we entered the land during the time of Joshua. Second, clearly she believed Jesus could heal her daughter and she didn’t care what her neighbors thought. She referenced David who had led many campaigns against her ancestors. But when you are desperate you do whatever it takes.
We must have walked a city block before this lady was really getting on our nerves. Her constant screaming was giving me a headache and I couldn’t concentrate or even hear what Jesus was saying as we walked. So finally, Thomas and I went to Jesus and said, “Please send her away. She’s driving those of us in the back crazy!” That’s when Jesus gave us the reason He had completely ignored her up to this point. “I was sent to the lost sheep of Israel.” Which I interpreted to mean, Jesus would have loved to help the lady, but if he did then everybody in this heathen land would follow Him and talk about a problem He would have when He returned to Israel. You see, Canaanites and Jews still didn’t get along. He could completely upset the social norms.
Anyway, after hearing this, Thomas and I went back to the lady and basically conveyed the same message to her. He would love to heal your daughter but our mission is to the Jews. And anyway, if He heals your daughter then our retreat is ruined. And we have been trying to get away for weeks now.
And I totally thought this would quiet the woman. I mean we weren’t mean. We were as just as kind as we could be. We didn’t want any trouble. We just wanted her to leave us alone. But instead of scaring the lady off, it emboldened her. She took off to the front of the pack and immediately fell at Jesus’ feet. And said, “Lord, please have mercy on me!” I couldn’t believe she could be so bold. I couldn’t believe she would call him, “Lord”. She barely knew Jesus. I don’t know how she even knew that He could heal her daughter. But one thing for sure, she believe in Jesus, maybe even more than we did.
That’s when Jesus stopped and probably said the harshest words I ever heard Him speak. Now hear me when I say this, they weren’t spoken in a harsh way. It wasn’t like Jesus had an air of superiority; He was just as humble and loving as He always was. But He looked her in the eyes (which is what He always did) and said, ““It is not right to take the children’s bread and toss it to the dogs.” Wow! Let that sink in for a moment. I don’t think Jesus meant it to be taken this way, but it sounded like He was calling her and her people dogs! Now that would be so normal for me or Peter to say, but not Jesus. He spent his ministry trying to tear down the prejudices so many of us had against others who weren’t like us. None of us will ever forget our trip into Samaria. But that is what Jesus said, “it is not right to take the children’s bread and toss it to the dogs!”
Surely this will send this lady on her way. He just insulted her whole race. She should storm off and get her friends together to beat us up. You shouldn’t go to another country and call them “dogs”. But that’s not what she did. And maybe God knew that is how she would respond which is why the Spirit had Jesus say what he said. I don’t know but let me tell you the most clever response I had ever heard. The lady looked up to Jesus and said, “But even the dogs get the crumbs that fall off the table”. Wow! Talk about an insightful response. How was Jesus going to respond? I guess He could tell her that He was a careful eater and He made sure no crumbs would fall. But that’s not what he said. In fact, now a smile came across His face. It was almost as if He was so proud of her answer. Then He said something He rarely said, “Woman, you have great faith! Your request is granted!” And the lady thanked Jesus and went on her way. A couple of hours later, we heard that the lady’s daughter was healed that very moment.
Interestingly Jesus didn’t say much more about the incident. He went back to teaching and we went back to learning.
But as I lay down to go to sleep that night, I couldn’t get what we had experienced out of my head. There was one big question that raced through my mind. I had left everything to follow Jesus. I had watched Him perform miracles. I had eaten the bread, He multiplied. I had watched Him walk across the sea. But He had never looked at me and said what He said to that Canaanite woman: “You have great faith”. If I was honest, Jesus often wondered why we had such little or no faith.
So what was the difference between the lady and me? Here is what I concluded. Great faith keeps crying when Jesus is silent. Great faith keeps coming when Jesus seems distant. Great faith keeps believing when the answer sounds like no. Great faith believes that even a crumb of God’s grace is enough. And lying that night, I prayed, “Lord, someday, let me have that type of faith”. What type of faith do you have? Let’s stand.
For Reflection and Discussion
- The Canaanite woman cried out to Jesus, but at first, “Jesus did not answer a word.” Have you ever experienced a season when you prayed and God seemed silent? What did that silence do to your faith?
- The woman kept crying out even when Jesus seemed to ignore her. Why do you think she refused to quit? What makes it difficult for us to keep praying when nothing seems to be happening?
- The disciples initially saw this woman as an annoyance rather than as a hurting mother. Are there people we sometimes view as interruptions, problems, or outsiders whom Jesus may be asking us to see differently?
- The woman continued coming to Jesus even when His words seemed to sound like “no.” How do you normally respond when God doesn’t answer your prayers the way you hoped?
- The woman essentially told Jesus that even a crumb would be enough. What does that reveal about what she believed concerning Jesus?
- If Jesus examined your faith today, where might He see persistence? Where might He be inviting your faith to grow?
One Question to Carry With You
Will I keep trusting Jesus even when He is silent, seems distant, or the answer sounds like no?
Behind the Sermon
This passage may have taught me more about the value of first-person preaching than any other in the series.
I wanted the listener initially to wonder whether Jesus was simply reacting the way we might react—tired, frustrated, wanting some peace—before circling back to the truth that Jesus never sinned and never made a mistake. I did not want to explain His silence away too quickly. That would have killed the story.
Living as Andrew allowed me to wonder why Jesus was acting this way even though the congregation already knew the ending.
The statement about Jesus being sent to the lost sheep of Israel required serious research. I tried to leave as much of that research in Andrew’s mouth as the facts would allow. But when Scripture did not give certainty, I resisted allowing imagination to manufacture it. Because I know God is good, holy, just, and kind, I am not afraid to say, “I don’t know.”
The great discovery came at the end. I seriously doubt I would have arrived at the “great faith” emphasis without preaching the passage in first person. Jesus’ words made me ask: What did He see in this woman that He was not seeing in His own disciples?
That question became the sermon.
First-person preaching often gives me something fresh in a passage I have preached before. The character does not change Scripture. The character changes where I am standing when I read it.
Give It a Try
Take a biblical story you know well—preferably one you have preached before—and look around the story.
Choose one person and ask: What did this person see? Hear? Know? Not know? What might have confused or surprised them? What did they see Jesus do that I have overlooked?
Do not give the character knowledge they could not possess. Do not let them know how the story ends. Do not be afraid to let them misunderstand.
Then ask: “What does this person notice that I have never noticed?”
Stand there for a while and listen.