I'm sure a lot has been lost in translation, about who and what constituted "rich" in the society of that time.
Besides, Jesus also asked of us to not judge anyone.
While pointing out hypocrisy and imperfection among some of those who considered themselves “righteous”, Jesus did not ask us “not to judge each other”.
Jesus was not the liberal dream of some “get along, go along, not my business what you do” kind of guy.
What He told us was that HE was not here to judge us but to prepare us for the time when God would surely do so.
Big difference.