Day 2829 – Is It Okay To Party With Sinners? – Luke 5:27-39

Welcome to Day 2829 of Wisdom-Trek. Thank you for joining me. This is Guthrie Chamberlain, Your Guide to Wisdom. Day 2829 – Is It Okay to Party With Sinners? – Luke 5:27-39 Putnam Church Message – 03/01/2026 Luke’s Account of the Good News - “Is It Okay to Party With Sinners?” Last week, we continued our study of the ministry of Jesus Christ with a message titled “Great Deeds, Strong Faith, Big God,” where we learned that when God becomes bigger, ministry expands, compassion deepens, faith strengthens, courage rises, and life changes. Today, we continue with the fourteenth message in Luke’s narrative of the Good News of Jesus Christ in a message titled “Is It Okay to Party With Sinners?” Our Core verses for this week are Luke 5:27-39, found on page 1599 of your Pew Bibles. Follow along as I read. SCRIPTURE READING — Luke 5:27-39 (NIV) Jesus Calls Levi and Eats With Sinners 27 After this, Jesus went out and saw a tax collector by the name of Levi sitting at his tax booth. “Follow me,” Jesus said to him, 28 and Levi got up, left everything, and followed him. 29 Then Levi held a great banquet for Jesus at his house, and a large crowd of tax collectors and others were eating with them. 30 But the Pharisees and the teachers of the law who belonged to their sect complained to his disciples, “Why do you eat and drink with tax collectors and sinners?” 31 Jesus answered them, “It is not the healthy who need a doctor, but the sick. 32 I have not come to call the righteous, but sinners to repentance.” Jesus Questioned About Fasting 33 They said to him, “John’s disciples often fast and pray, and so do the disciples of the Pharisees, but yours go on eating and drinking.” 34 Jesus answered, “Can you make the friends of the bridegroom fast while he is with them? 35 But the time will come when the bridegroom will be taken from them; in those days they will fast.” 36 He told them this parable: “No one tears a piece out of a new garment to patch an old one. Otherwise, they will have torn the new garment, and the patch from the new will not match the old. 37 And no one pours new wine into old wineskins. Otherwise, the new wine will burst the skins; the wine will run out and the wineskins will be ruined. 38 No, / new wine must be poured into new wineskins. 39 And no one after drinking old wine wants the new, for they say, ‘The old is better.’” Opening Prayer Heavenly Father, thank You for Your Word, and thank You for sending Jesus to seek and save the lost. Open our hearts today so that we do not merely hear this message, but receive it. Where we have become rigid, soften us. Where we have become fearful, steady us. Where we have become proud, humble us. And where we have withdrawn from the people who need Your grace, send us out again with the heart of Christ. Teach us what it means to be holy without hiding, / loving without compromising, / and joyful without pretending. May Your Spirit guide every word and every listener today. In Jesus’ name, amen. Introduction Today, we come to one of those passages that exposes us a little. It is one thing to say, “Jesus saves sinners.” It is another thing to watch how He does it. And in Luke 5, He does not save sinners from a distance. He does not shout grace from across the street. He does not wait for the broken to clean themselves up, / learn the language, / and enter the synagogue respectfully. He walks right up to a tax collector’s booth. He calls a man everybody else has written off. Then He goes to that man’s house and sits down at his table with the kind of people religious society avoids. And the religious leaders are scandalized. Not because Jesus is sinning. But because He is too close to sinners for their comfort. That is the tension in this passage. And if we are honest, it is still the tension in many churches today. We love a ministry that looks clean, organized, and respectable. But Jesus often does His best work in messy rooms, crowded tables, uncomfortable conversations, and unexpected friendships. So, the question is not merely, “Is it okay to party with sinners?” The deeper question is: Do we have the heart of Christ for people who are still far from God? This passage answers that question powerfully. Main Point 1 Jesus Calls the Person Everyone Else Has Counted Out (Luke 5:27–28) “Later, as Jesus left the town, he saw a tax collector named Levi sitting at his tax collector’s booth. ‘Follow me and be my disciple,’ Jesus said to him. So Levi got up, left everything, and followed him.” (Luke 5:27–28, NLT) Let’s slow down and feel this moment. Jesus is not walking through town looking for the most polished candidate. He is not recruiting from the synagogue leadership. He is not interviewing the men with the best religious resumes. He walks to a tax booth. And there sits Levi. Now, to us, “tax collector” may sound just ...