Before anything, if you want an accurate translation, give us the context of that sentence please.
Aside from that, here's how I would understand it at first glance: It may make a man scratch where he doth not itch
It may make a man uncomfortable/embarrassed/surprised (hard to say without context) to see a man live poor to die rich.
Here the "poor/rich" can be interpreted in many ways:
It could be "poor" in the sense of strict and restrained, so that he can spare money, resources whatever over time and die after having accumulated many riches, thus being rich. that's a very literal way to interpret it.
It could also be "poor" as a synonim of improper. He's done many bad things, robbed people and lived on "poor" moral principles to become rich.
Those two are just the ones I could think of like that, I'm sure there are other ways to understand it.
Having the context to that sentence might help narrowing it down.