I first preached on this text when I was assisting at All Saints in Princeton, and while the text in front of me was Luke I decided to preach off of Matthew and talked for the entire sermon about what it means to be poor in spirit. This was in the 70s when churches were still full. After the Family Service I would lead a group of about 40 in adult ed and the Rector would lead a larger group on a different topic. For a variety of reasons, I was doing all of the preaching at the Family Service and we were in a period in which my adult ed group reacted to my sermon. So after the Eucharist I went to the meeting room and about 40 men and women told me what they thought of my sermon. They were mostly polite. People are usually polite to the preacher. But a Princeton professor spoke up and said that I had failed.
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