During the Ash Wednesday liturgy, my Jewish wife was offended to hear Jews referred to as "hypocrites." How can I explain to her why Jesus would say such a thing about her people?
Jesus was a Jew himself and was certainly not calling all Jews hypocrites. There are hypocrites in every group (Catholics included). In the Gospels, when Jesus uses terms such as “hypocrites” to describe the people with whom he was dealing, he was not addressing that word to all Jews of his time or all Jews of all time, but rather to those he was interacting with at the time.
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