Luke 19:2 says “Here was a man by the name of Zacchaeus; he was a chief tax collector, and he was rich.”

In those days, being a tax collector was sort of a franchise. You paid the Romans an up-front fee and then a percentage of your take. But you kept the balance. This was a path to riches, and to becoming the most hated man in your neck of the woods.

The Jewish community considered tax collectors so compromised, so ceremonially and morally unclean, that they were grouped in religious literature alongside prostitutes. They were barred from giving testimony in court. They could not hold religious office.

In the eyes of their own community, they had forfeited their place among the people of God. They were traitors, collaborators, and thieves, all three at once, and Zacchaeus was the most successful one in town.

His name, incidentally, means pure or innocent. The irony was not lost on any one hearing this from an Apostle.

It seems he was a short little man, with all the insecurities one often finds in shorter people.

Luke continues: Zaccheus was trying to see who Jesus was, and was unable because of the crowd, for he was small in stature. So he ran on ahead and climbed up into a sycamore tree in order to see him, for Jesus was about to pass through that way. When Jesus came to the place, he looked up and said to him, “Zaccheus, hurry and come down, for today I must stay at your house.”

Now in those days (and now), to have someone over for dinner suggests at least a certain level of honor. We rarely invite people we consider pond scum into our homes. Nor do we choose to dine with those we consider pond scum.

Jesus looked at the most hated man in Jericho and said publicly, in front of a crowd of people who had been waiting to see a miracle: I’m going to his house. Today.

The crowd’s reaction tells you everything. When they saw it, they all began to grumble, saying, “He has gone to be the guest of a man who is a sinner.”

Now, the word grumble in the Greek, διεγόγγυζον (diegongyzon), is the same word used in the Septuagint for Israel’s complaints in the wilderness. Luke’s audience, steeped in the old testament, would have caught the comparison immediately. They were as unhappy at Jesus’s behavior as the Israelis had been when lost in the desert. This is not a mild grumble – it’s a shock.

What happens next is even more of a shock. Zaccheus immediately says to Jesus that he will give half of my possessions to the poor. And if I’ve defrauded anyone I will pay back four times over.

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

Jesus had not asked Zacchaeus to clean up his act first. He had not required a confession before extending the invitation. He walked up to the man and offered him relationship before Zacchaeus had done a single thing to earn it.

Half his possessions to the poor. Torah did not require this. There is no commandment that says give away fifty percent of everything you own. This was radical, voluntary, economy-altering generosity that would have fundamentally changed Zacchaeus’s financial position.

Four times as much for anyone he had cheated. This is where it gets really precise. Exodus 22:1 required fourfold restitution for the theft of livestock, animals that could reproduce and whose loss compounded over time.

It was the Torah’s highest restitution requirement, reserved for the most serious categories of theft. Zacchaeus was not meeting the legal minimum. He was voluntarily applying the maximum standard to his own case, treating every act of extortion as worthy of the most serious Torah consequence.

This is not a man making a general promise to do better. This is a man who knew the law, named the specific legal remedy, and applied it to himself without being asked. He was stating his own guilt and his own sentence in the same breath and doing it in front of a crowd that despised him.

The key point is that Jesus extended grace before repentance came. He offered relationship before Zacchaeus had done anything to deserve it. And that grace, that completely unearned, publicly scandalous, crowd-offending grace, is exactly what produced the repentance. Zacchaeus did not clean himself up and then get invited to dinner. He got invited to dinner and the invitation changed EVERYTHING.

The crowd thought the question was whether Zacchaeus was worthy of Jesus’s company. Jesus was not interested in that question. His question was whether Jesus was lost and whether he could find him. And the answer was yes and yes. He was the one amongst the ninety-nine.

The Son of Man came to seek and save the lost. Not the almost-lost. Not the lost who had already started making their way back. The ones still up in trees, watching from a distance, fairly certain they were too far gone to be the ones He was actually looking for. This is a pretty high bar for the rest of us.

I’m not sure I could extend grace, friendship, or much of anything else to Stephen Miller. He’s the one really pulling the strings at the White House, then man who wrote much of Project 2025, the man who is ripping babies from their families, the man who is terrified there might be more Americans with brown skin. Perhaps Jesus will use his grace for Stephen, and the cabal of others in the White House who are treating Americans far worse than Zacchaeus treated his neighbors. ‘Tis a thing devoutly to be wished for, but I am not my breath holding.