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5 Bible Characters’ Worst Moments in the New Testament

What’s the first thought that often enters a child’s mind when he does something wrong and realizes he’s been caught? Hide! How often do we have these same thoughts as adults when we realize that our Heavenly Father sees our mistakes? Perhaps we don’t talk to Him for a little while because we are afraid of what He might say. Maybe He didn’t notice because He was so busy with someone else. We might skip out on church or hanging out with our friends who are Christ followers. Anything to not be confronted with our sin.

The New Testament is filled with examples of people messing up time and time again (We’re all human.). Here are five examples of when Jesus caught people red-handed in their worst moments and how He reacted to their current predicaments.

The Samaritan Woman-

Scripture: “…Jesus said to her, ‘You are right when you say you have no husband. The fact is, you have had five husbands, and the man you now have is not your husband. What you have just said is quite true.’” - John 4:17

Context: Jesus had the nerve to waltz into Samaria early on in His ministry. What’s the big deal about that? Jews and Samaritans were like the modern-day Hatfields and McCoys. They knew to stay away from each other or there would be trouble. So was Jesus looking for trouble this day in Samaria? Not quite…He had a divine appointment with a woman in the middle of the heat of the day at a well. He shocked the woman by speaking to her and asking for a drink of water (Talking to a woman, and she’s a Samaritan? Two strikes already.). Jesus began to talk to her about the difference between the water in the well and living water. The woman doesn’t quite seem to get what’s going on here, so Jesus tells her to go get her husband. “Well, there’s a little problem,” she tells Him. “I don’t have a husband.”

Jesus responds, “Yeah, I know that. You’ve had FIVE and the dude you’re with now isn’t your husband.”

Yikes. Jesus has caught this woman in the middle of a life most likely filled with affairs and lies. She’s been trying to hide from everyone in her shame by coming to the well in the heat of the day, and He straight up shows up and drops the mic.

God’s Forgiveness Visible: Jesus greets this woman with an offering for eternal life, knowing who she is and that she is currently living with a man who she is not married to. He continues His offering of salvation even when she does not seem to understand His words. He takes the time to meet her where she’s at and doesn’t leave until she gets it. And boy, does she get it! Remember those people she was hiding from in her town? She goes running to tell every single one of them that the Messiah has come.


Scripture: “Jesus entered Jericho and was passing through. A man was there by the name of Zacchaeus; he was a chief tax collector and was wealthy.” - Luke 19:1-2

Context: Ever heard the song phrase, “Zaccheus was a wee little man and a wee little man was he”? Is that even kosher anymore? I digress. This is the guy mentioned in the children’s song. He was a tax collector. Now, you’ve got to understand that tax collectors were considered scum to Jews. They worked with the enemy (Rome) and cheated the Jews out of so much money. Luke 19 mentions that Zaccheus was loaded. He had been cheating people out of their money for a long time. Zaccheus was working as a chief tax collector when he heard Jesus speaking in Jericho. He ran and climbed a tree just so he could see and hear Jesus.

God’s Forgiveness Visible: Jesus notices Zaccheus in the tree, calls to him, and invites Himself over to Zaccheus’ house. Way to self-invite, Jesus. All these people who were listening to Jesus hear Him talking to Zaccheus and their jaws drop. Like, what are you doing talking to this dirt bag? Don’t you know what he’s taken from us? Zaccheus is super excited that Jesus sees past his failings, and he tells Him right then and there, ‘Look, Lord! Here and now I give half of my possessions to the poor, and if I have cheated anybody out of anything, I will pay back four times the amount.’” Heyooo! This dude gets it and Jesus is totally stoked. Salvation has come to the sinner.


Scripture: “And after an interval of about an hour still another insisted, saying, ‘Certainly this man also was with him, for he too is a Galilean.’ But Peter said, ‘Man, I do not know what you are talking about.’ And immediately, while he was still speaking, the rooster crowed. And the Lord turned and looked at Peter. And Peter remembered the saying of the Lord, how he had said to him, ‘Before the rooster crows today, you will deny me three times.’ And he went out and wept bitterly.” - Luke 22:59-62

Context: Peter’s one of Jesus’ closest friends. He gives 110% in everything he does. This is the guy who walked on water for a minute and who washed Jesus’ feet. But he has a pride problem. We see it when Jesus is telling the disciples that He is going to suffer in Jerusalem and be killed and rise again; Peter cries out, “Never, Lord! This shall never happen to you?”

Jesus reels around and spits, “Get behind me Satan!”

And once again, we see it after Jesus is indeed arrested and has begun to suffer. Three times Peter is “accused” of being with Jesus’ crew, and he blatantly denies it. Right after the third time Peter swears he doesn’t know Jesus, Luke says, “The Lord turned and looked at Peter.” Holy cow. What a haunting picture to try to erase.

God’s Forgiveness Visible: After Jesus’ resurrection, He makes several appearances, one taking place by the Sea of Galilee. Jesus takes the wrecked Peter aside and brings him out of his low place and reconciles him to Himself. He commissions Peter to feed His sheep; a command only given to believers. Jesus has forgiven Peter’s denial and calls him to eternal devotion.

The Thief on the Cross-

Scripture: “‘When they came to the place called the Skull, they crucified him there, along with the criminals—one on his right, the other on his left.’” - Luke 23:33

Context: We don’t know much about the two men hung on crosses beside Jesus. Some translations call them rebels, others thieves or robbers. Whatever they did, the Romans found this to be worth a terrible death. One thief mocked Jesus telling him if He was so high and mighty, He should save them all. The other thief rebuked the former. He told him, “Hey, we did something wrong and deserve our punishment; He didn’t. Chill out.”

Then the thief gets really brave and asks Jesus to not forget about him in the next life.

God’s Forgiveness Visible: Jesus makes a promise to this criminal that he will join Him in paradise. The guy has made a decision in his last moments to follow Jesus, and Jesus is all about it. He doesn’t look at the guy’s past or the amount of time he has believed; He sees his short time of faith and still redeems him.

Saul of Tarsus-

Scripture: “He fell to the ground and heard a voice say to him, ‘Saul, Saul, why do you persecute me?’” - Acts 9:4

Context: A devout Pharisee all his life, Saul felt threatened when he heard people claiming Jesus had risen from the dead. The man held the coats of those who stoned Stephen, the first martyr. He went on a rampage killing Christians. He thirsted for their blood. But the day came when Jesus said, “Enough.”

He blinded Saul and crushed his spirit.

God’s Forgiveness Visible: Jesus sends a man named Ananias to restore Saul’s sight after Saul is blind for three days. He tells Ananias that He has great plans for Saul. He’s going to play an amazing role in proclaiming the Gospel to the ends of the earth. This man, Saul, who we often recognize as Paul, ended up writing about half of the New Testament.

Jesus used some pretty radical situations to show that He saw these people no matter what was going on in their lives. Jesus sees us in our worst moments, too. We can’t hide from Him. But we can run to Him. Forgiveness is always there for the taking.

So is that it, we can just do whatever we want and run and say we’re sorry without any consequences?

There are consequences. And there was a cross. Let’s never forget the cost of our mistakes. But let’s also remember how merciful our Heavenly Father is and be thankful for His grace. Just like He did for these five believers, let’s ask Him to take each one of us out of the mire and use us for His glory.

Looking for songs about God forgiving us in our worst moments?

Check out these songs from Red Letter Society:


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