Respectability does not always accompany wealth. Though many do earn their wealth honestly through hard work, industriousness, and the blessings of God, others are outright crooks. Even worse, some make their money legally but immorally, for not everything immoral is illegal, as we all know so well.
Jericho, Zacchaeus’ residence, had become a significant commercial center and housed the Herodian palace. Because of its geographical location, it maintained a customs gathering station. Zacchaeus could have easily enriched himself legally as the chief regional customs officer. The narrative, however, suggests that greed induced him to overstep legal boundaries. Zealous patriots despised even honest customs collectors, seeing them as tools of their Roman oppressors, but they greatly disdained dishonest ones like Zacchaeus. Matthew (Levi) occupied a similar position in Capernaum, under Herod Antipas. Essentially having assumed the role of Roman governmental agents, they were viewed as traitors, or worse yet, thieving traitors.
Nonetheless, Christ was not deterred. Defying social constraints, Jesus dined with them, drawing intense criticism from priests and commoners alike. And, by Jesus’ interaction with them, these despised men were eventually won to the gospel, Matthew not only becoming one of the twelve disciples but an author in the New Testament!
Again, we should be careful about the kind of spiritual judgments we make about people. Though not all sins are of the same magnitude, and some are certainly socially worse (and with good reason) than others, all of us are equal before God in that we are all in need of the righteousness of Christ.
Think of some well-known but despised (and perhaps understandably so) personage in your culture. Imagine what it would be like if you had a chance to witness to that person. Would you even want to? What would you say?