Better is the poor that walketh in his uprightness, than he that is perverse in his ways, though he be rich.
Better to be poor and honest than to be dishonest and rich. (NLT)
There was once a vertically challenged tax collector who climbed into a tree to see over the heads of the crowd when a famous itinerant Teacher came to town. The gentleman in question was reasonably wealthy, but should not have been. Why not? Because he was a civil servant. He gained his wealth not through fair wages but by cheating the taxpayers of the town. Did he feel any discomfort or remorse about the way in which he accumulated his riches? Possibly not, but something drew him to a Teacher with no visible wealth, just a wealth of wisdom in His words.
The tax collector was called Zacchaeus. When the Teacher came to the tree he looked up and told Zacchaeus to come down out of the tree, and immediately invited Himself to dinner. The dinner party that followed was a life-changing event for Zacchaeus and resulted in him donating half of his wealth to the poor. The reminder probably went in the compensation he promised to anyone he had ever cheated. Scripture does not say that Zacchaeus was reduced to a life of poverty because of his encounter with the Teacher, but it seems likely. Not everyone who met Jesus was changed in this way, but everyone has a choice. Listen to the words of eternal life, or walk away (as one rich young man did).
This proverb is very similar to Proverbs 19:1, which also teaches that it is better to be poor and honest, than dishonest and a fool. The fact of the matter is that God does not measure wealth in worldly terms, but examines each human heart to discern whether wisdom is present and in what quantity. Zacchaeus appears to have been blinded by the shiny things of the world, but had sufficient wisdom to recognize the need for change in his life. His encounter with Jesus didn’t just change his life, but totally transformed it. I can’t imagine that anyone in the crowd saw that one coming.