Jesus had a knack for going places, doing things, and connecting with people that others—mainly the religious crowd, although on occasion, even his own disciples—didn’t think were appropriate for a devout, God-fearing Jew.  

 From traveling through Samaria to connect with a woman who needed to hear he was the Messiah, to touching and being touched by both the morally and physically unclean, to sitting down to meals with “tax collectors and sinners,” Jesus befriended the unexpected (Matthew 9 &11; Mark 2; Luke 5, 15; 19).

The story of Zacchaeus is one example of how to engage with people whose lives and lifestyles we find to be outside of God’s ideal. Let’s revisit the story from Luke 19:1-10: 

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. He wanted to see who Jesus was, but because he was short he could not see over the crowd. So he ran ahead and climbed a sycamore-fig tree to see him, since Jesus was coming that way. 

When Jesus reached the spot, he looked up and said to him, “Zacchaeus, come down immediately. I must stay at your house today.” So he came down at once and welcomed him gladly. 

All the people saw this and began to mutter, “He has gone to be the guest of a sinner.” 

But Zacchaeus stood up and said to the Lord, “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.” 

Jesus said to him, “Today salvation has come to this house, because this man, too, is a son of Abraham.  For the Son of Man came to seek and to save the lost.” 

Classic Jesus, reaching out to the lost, marginalized, ostracized, bringing a happy ending— not only was Zacchaeus saved, but he offered restitution for all his swindling.

 In the Israel of Jesus’s day, there were categories of people who were outsiders. People who were shunned, ridiculed, devalued, and ostracized. From entire people groups, like the Samaritans, to those who made immoral or unethical livings, like tax collectors or prostitutes (generally referred to as “sinners”), to those who, through their own choices or simply through the lamentable brokenness of the world, found themselves “unclean” and living as outsiders.  

Tax collectors were among the most reviled and ostracized groups of Jesus’s day. Jews couldn’t understand why anyone would choose to be a tax collector. It seemed to be a rejection of God and their own people. They were siding with the enemy: Rome. True, tax collectors could buy friends— there were plenty of well-attended parties at their homes, but those parties were looked at with disdain by those considered God-fearing. They were gatherings of “tax collectors and sinners.”  

It’s not hard to think of a few groups of people who’ve experienced the same “outsideness” in our day. Some have been ostracized because of their lifestyles (chosen or otherwise), and others have been oppressed because of the sinful impulses of our power structures.  

 But here’s something important to note; while most of the story happens between Jesus and Zacchaeus, there’s a little cut away in verse 7 to the scene outside: “All the people saw this and began to mutter, ‘He has gone to be the guest of a sinner.’”

It’s not an unfamiliar grumble. In the gospel of Matthew, the author remembers his own calling to follow Jesus. While Jesus had dinner with Matthew, “many tax collectors and sinners came and ate with him and his disciples” (Matt. 9:10). And again, the low murmur of disapproval could be heard in the background. The religious leaders asked his disciples, “Why does your teacher eat with tax collectors and sinners?” (v. 11).

On some occasions, the disciples too were accused of being defiled and breaking the law, making them sinners (see Matt. 12:1-2, 15:20; Mark 7:1-5). As New Testament scholar, Lynn Cohick, recently reminded me, the strict principles of the religious elite in Jesus’s day would’ve placed everyone in the category of sinner. This wasn’t a category reserved for people engaged in a certain kind of behavior or lifestyle. This included everyone, you and me alike.

Matthew even wrote about his own calling from tax collector to disciple. He wanted to make it clear: he was one of the sinners Jesus came to call. It’s a reminder we need, too. In our efforts to live for and like Jesus, we too often forget that we would’ve been part of the groups receiving the grumbles of the crowd and the religious leaders. And we still find ourselves in need of Jesus’s acceptance, love, and forgiveness. 

So, when we read these stories about what Jesus did and with whom he associated, we should find solidarity with those eating with Jesus, and not those grumbling from afar. We don’t sit in judgment of others, we rejoice that God found us and called us into his life, and we then echo his call and invite others into his life, too.

Jesus is called a friend of sinners (Matt. 11:19; Luke 7:34). Them and us.

No matter what we might say about his intentions, or the outcome of such friendship, Jesus associated with sinners in a relational way before any change or repentance on the part of the sinner. Jesus’s initial message to the sinners, by his very presence with them, was that they mattered. They, as people—not as behaviors, not as lifestyles, not as moral choices—were important.   

This can be seen clearly in Jesus’s interaction with the woman at the well in John 4. Jesus deliberately went out of his way to meet her. It was a divine appointment that would show the disciples and the Samaritans (included in the above list of outsiders) the nature of the kingdom of God.  

The very sound of his voice probably startled her. She knew he was there— he was sitting at the well when she walked up, but she thought Jesus would ignore her, especially by virtue of her race and her gender. Those in her own town had, it seems, made her an outcast, which is why she was at the well, alone, during the hottest part of the day. She was the outcast of the despised—the unclean of the unclean.

 But not to Jesus. Not to the friend of sinners.

To him, she mattered. To him, she was worth time. Though he knew her story, that wasn’t the focus of his attention. The first thing he did was connect with her, to show her that she was important. Important enough to go out of the way to meet, to talk to, to share with.  

This shouldn’t surprise us. Jesus said, “I have not come to call the righteous, but sinners” (Matthew 9:13).  For Jesus, calling sinners didn’t mean standing at a distance and shouting, “Hey, what you’re doing is wrong! Stop that and come over here!” Rather, it meant going to where the sinners were and being with them.

Though his actions were almost always misunderstood by the religious community as either supporting or endorsing sinful behavior (which he wasn’t), Jesus let people know they were important to him. Implicitly, he was also telling the religious community they were wrong, both about him and for ostracizing sinners instead of reaching out to them.

He made sure they understood they weren’t innocent when it came to the laws of God, despite what they may have thought (Matt. 15:1-20).

 He wasn’t concerned about his reputation or the gossip that came from his association with sinners. Jesus would’ve rather been labeled a sinner, glutton, and drunkard than fail to reach out to people who needed to experience his love and compassion (Matt. 11:19; Luke 7:34). 

Certainly, there’s something for us to wrestle with here, both in perception and actuality.  

Was Jesus, by his association, endorsing their lifestyle and choices? Of course not. He recognized they, like us, were sinners in need of repentance. That sin, however, didn’t keep him from seeing their value as people and connecting with them. It’s possible to be friends with sinners, to spend time with them, develop relationships with them without endorsing or minimizing sin. Jesus recognized that sin isn’t the place to start. Jesus started with the person, not whatever choices they’ve made or continued to make. 

Jesus’s actions in these stories lead us to ask some really important questions too. What role, if any, does the opinion of others impact our reaching out to people who don’t know Jesus? What if people assume the worst of us? That we’re condoning sinful lifestyles or that we’ve softened or changed the gospel? That certainly seems plausible. They did it to Jesus, why wouldn’t people accuse us of something similar? 

And yet, Jesus’s words come full circle in this regard. When he was accused of being a sinner himself, he responded, “Wisdom is proved right by all her children” (Luke 7:35). Not exactly “the ends justify the means,” but Jesus is saying the tree should be judged by the fruit that comes from it.  

 Back to Zacchaeus. 

Clearly, Jesus’s visit was significant. In short order, Zacchaeus declared he’d make his past actions right. While we don’t get any further information, it’s fair to assume he’d no longer cheat people in their taxes, though he may have stayed a tax collector. This is the story of Zacchaeus’s repentance and salvation. This is the result of Jesus’s presence and conversation in Zacchaeus’s home. Jesus never wavered from his mission of seeking and saving the lost and calling sinners to repentance. 

So, too, in our relationships. When we reach out, and we should form relationships with those who don’t know Jesus, we can’t forget we’re showing them Christ. This may take longer than the dinner Jesus shared with Zacchaeus, and it may, in fact, give more time and opportunity for people to misunderstand or misjudge our actions.

But relationships aren’t simply a means to an end. We don’t simply care until they’re saved. Rather, we care enough about people, perhaps maligned, misunderstood, alienated people, to reach out with compassion and understanding, because we too want and need that same compassion and understanding. Our goal? To show the love and grace of Jesus. And when they hear the call of the Lord and respond, they’re part of his family, part of our family, an outcome in the here and now, not waiting for us in heaven.

We need to pause here and consider this in both the story of Zacchaeus and the woman at the well. Jesus said that he came that we might have life, and have it to the full (see John 10:10). In both the encounter with the woman at the well and Zacchaeus, there was an immediate change in their lives. And this doesn’t seem like the guilt-laden moralistic change that’s the result of condemnation. Both people seem exuberant after their encounter with Jesus. They’re invigorated and energized, joyful in their expressions. Words and deeds both reflect a new life that’s been given to them. 

Jesus came to offer all of us life. Not just life with him after our bodies find their way back to the ground from which we all came, but full life here and now. He offers us life that continually fills with love, joy, peace, patience, kindness, goodness, faithfulness, gentleness, and self-control (Gal. 5:22-23).

Of course, there are things a follower of Jesus shouldn’t do. There are places that might not be wise to go. But are there people we shouldn’t connect with? I pray the answer to that isn’t difficult. How do we share the love of Jesus if we don’t connect with the people who don’t yet know that love?  

So, what do we do? 

  1. Remember that when Jesus said he came to call the sick and the sinners, that includes all of us. We don’t distance ourselves from others as if we’re better than them.
  2. Recognize everyone is in need of Jesus, but some have also been marginalized and ostracized by their, and our own, communities. 
  3. Accept that reaching out doesn’t mean standing at a distance and judging their behaviors. Rather it means going to, and walking with, them to show the love of Jesus.
  4. We don’t invite people into moral transformation. We invite them into the full life Jesus offers. We invite them into life in the image and likeness of Jesus himself.
  5. Embrace the possibility that others may question your associations, while realizing that connection does not mean endorsement. 
  6. Show, through words and deeds, the love of Jesus to those who need it, and that is everyone.