Why Jesus Chose a Traitor: The Story of Matthew a Tax Collector

This article has been taken from content of the same information at Whiskey and the Writings. For that video, click here.

For this week’s writings, I want to take us into a story that doesn’t often get the emotional weight it deserves. It’s the story of Matthew—the tax collector Jesus invites into discipleship in Matthew 9. If you’ve grown up in church, you might’ve heard it before. But what I want to do is slow it down, explore what’s going on behind the scenes, and maybe, just maybe, uncover something that speaks to all of us who’ve felt like outsiders—like we don’t belong anymore. Or never did.

Let’s start with the context.

Matthew’s Gospel was written primarily to a Jewish audience. That’s important, because it explains some of the distinct language and structure you’ll find throughout his writing. Think of Matthew’s Gospel as trying to convince his fellow Jews: Hey, this Jesus isn’t a detour. He’s the fulfillment. There are echoes of Moses all over the place—Jesus as the new liberator, the bringer of a new law, a new way forward. You’ll even notice Matthew using phrases like “kingdom of heaven,” whereas Mark or Luke would say “kingdom of God.” That wasn’t a mistake. It was an intentional choice to use language that honored the Jewish reverence for the name of God.

So when we get to chapter 9, and Jesus calls Matthew—a tax collector—it’s not just a narrative footnote. It’s a disruption. It’s a moment that challenges everything his Jewish audience thought they knew about who belongs and who doesn’t.

Here’s the passage:

“As Jesus went on from there, he saw a man named Matthew sitting at the tax booth. ‘Follow me,’ he said to him. So he got up and followed him. As Jesus was having a meal in Matthew’s house, many tax collectors and sinners came and ate with Jesus and his disciples. When the Pharisees saw this, they said to his disciples, ‘Why does your teacher eat with tax collectors and sinners?’ When Jesus heard this he said, ‘Those who are healthy don’t need a physician, but those who are sick do. Go and learn what this saying means: “I want mercy and not sacrifice.” For I did not come to call the righteous, but sinners.’” — Matthew 9:9–13 (NET)

On the surface, it reads like a simple story: Jesus calls a guy. The guy follows him. Then there’s dinner. But if we rush past it, we’ll miss the emotional, social, and theological earthquake happening in this moment.

Here’s why it matters.

Matthew wasn’t just a tax collector. He was a collaborator. Rome had occupied Judea, and taxes were a constant reminder that they were under foreign rule. But it wasn’t just that taxes were being collected—it was who was collecting them. Rome often hired local Jewish citizens to do the job, which meant someone from your own neighborhood was taking your hard-earned income to fund your oppressor’s empire. It was betrayal wrapped in bureaucracy. Matthew wasn’t just disliked. He was despised. He was the enemy from within.

And yet Jesus walks up to that guy and says, “Follow me.”

No conditions. No prerequisites. No theological interview or moral reform first. Just an invitation.

And that’s where it gets personal. Because some of us are carrying a lot of shame. Some of us have been told—explicitly or implicitly—that we don’t belong. Maybe it’s because of questions we ask, doubts we carry, political affiliations, gender roles, sexual ethics, past wounds, or current habits. Whatever it is, the church often frames belonging in black and white: you’re in or you’re out. But here’s Matthew, sitting in the messy, complicated gray—and Jesus doesn’t flinch. He doesn’t draw a line in the sand. He walks right up to it and says, “Come with me.”

And Matthew does.

What happens next is even more surprising. Jesus doesn’t take Matthew to the synagogue. He doesn’t say, “Cool, now that you’re following me, come into my world.” No, Jesus goes to Matthew’s house. He enters Matthew’s space, sits at Matthew’s table, and eats with Matthew’s friends.

This is huge.

In the ancient world, meals weren’t just about food. They were declarations of acceptance. To eat with someone was to say, You belong with me. So when Jesus eats with tax collectors and “sinners,” he’s not just being polite. He’s breaking religious protocol. He’s saying, “This is where I want to be. With them. At their table.”

Of course, this doesn’t sit well with the Pharisees. And I want to be fair here: Pharisees weren’t cartoon villains. They were a group deeply committed to seeing Israel restored. They believed if the Jewish people returned to Torah—if they could just get their spiritual act together—God would return to rescue them. So they built systems around the Law, trying to help people stay faithful. But like many institutions, what started as devotion turned into control. The desire to be holy became the justification to judge.

So they see Jesus at this table and they don’t understand. They say, “Why does your teacher eat with these people?” And Jesus replies with one of the most beautifully subversive lines in Scripture: “I didn’t come for the healthy. I came for the sick. I desire mercy, not sacrifice.”

That line is everything.

Because some of us—maybe even you reading this—are carrying spiritual wounds. You’ve been made to feel like your questions make you unfaithful. Like your brokenness disqualifies you. Like you’re on the outside because you don’t conform to the system. And maybe you’ve even come to believe that’s how Jesus sees you too.

But this story tells a different story.

Jesus goes to Matthew before Matthew cleans anything up. He meets him at his table. He meets him in the mess. And he brings healing not by demanding change first, but by offering presence, relationship, and dignity.

I resonate with Matthew. I’ve spent over two decades in pastoral ministry, trying to faithfully serve communities I love. And yet, in this recent season, I’ve felt pushed out—not because of scandal, but because I’m willing to talk about doubt. Because I create space for questions. Because I don’t always land in the theological boxes that others are comfortable with. I drink bourbon and talk about the Bible. I wrestle with women’s roles, with how we understand Genesis, with whether we’ve truly grasped the story we claim to live by. And for that, I’ve been treated like a threat.

So when I read this story, I don’t just see Matthew. I feel Matthew. And maybe you do too.

Maybe you’re not sure where you belong anymore. Maybe church has become a place of anxiety instead of peace. Maybe you’re deconstructing, not because you’ve lost your faith—but because you’re trying to rebuild something more honest. If that’s you, I want you to hear this: You are not on the outside of Jesus.

In fact, you may be closer to him than you’ve ever been. Jesus doesn’t wait for the religious system to validate you. He meets you at your table and says, “Follow me.” That’s the beginning of healing. That’s the place where wholeness begins.