Taxes have never been popular.
|Zacchaeus in the Tree by William Hole, 1908|
Zacchaeus was not a regular tax collector, he was chief among them. For Jews living at the time, he must have been seen as a real collaborator with the Romans. The frustration for many would have been along the lines of, "how could the Messiah who is coming to free us from Rome, be eating in the home of a Jewish traitor like Zacchaeus?"
Jesus sees beyond the politics of the day. The freedom he is bringing is larger than governance and more personal at the same time.
Because people weren't getting it, Jesus tells the story about the King who entrusted money to his servants. The King had expectations and some succeeded while others failed. When Jesus embraces Zacchaeus and he changes for the better, this is a win. When others shun those they consider sinners and they remain outside of the larger relationships with the community, this is like wrapping up the money in scarves.