Beginning negatively

To understand Zacchaeus involves giving a little background.  Publicani were a class of people in efficient Roman society, and it was ruthlessly efficient, that were public contractors responsible for a number of tasks, of which tax collecting was the most obvious. The right to collect taxes for a particular region would be auctioned every few years for a value that (in theory) approximated the tax available for collection in that region. Jericho was a wealthy area. Any excess (over their bid) in tax collected would be pure profit  That could be a big deal!  

Publicans were monied, powerful and detested. For Zacchaeus and others like him were Jews, who had defected to serve the hated Roman occupiers. Betraying their own people they now had authority to extract extra money, to rob their national family. We can imagine this job took a particular kind of person. They had to have some money in the first place, perhaps Zacchaeus' Dad was a tax collector so that bidding in the auction was a family thing.  But they needed personality hardened enough to withstand hatred and envy from their own people,  That’s why they were bracketed - publicans and sinners. 

They really had set themselves against God’s people and against God. And the chief tax collector was top of the pile of rich betrayers.  He didn’t mind being unpopular (we see that in the story), because you really can’t have enough money. You really had to be money-crazy to put up with being hated every day But money does that. It brings the worst out of people and when you’re in love with it enough there’s hardly any limit to which you will cut corners, cheat friends, trample on strangers. The background chant could be the Abba lyric: Money, money, money always sunny in the rich man's world,  Aha it's a rich man's world. Somebody had to do this job and just look at what it has given him in wealth and status.. 

As we meet Zacchaeus he doesn’t seem to have much going for him. A totally negative character. Not likely to become a friend!