Matthew collects a great many of Jesus’ teachings and puts them in one place spanning chapters 5 – 7. It doesn’t seem to matter much whether he really said all of these things in one sitting or whether he taught various bits at various times, likely repeating many bits in different settings. And it doesn’t strike me as deceptive writing to gather them all in one place if they weren’t in fact taught that way; nothing in this Gospel hinges on the idea that this is one sermon.
The Beatitudes are a short list of qualities or situations that Jesus calls blessed or happy.
Many of them address what could be considered positions of weakness — mercy, spiritual poverty, meekness, gentleness, etc. The charge of weakness may be especially poignant in a time when many were poised for a militaristic revolution against the Roman occupation. Jesus wants us to know that his way does not call for violence, aggression, and force. That said, mercy and the like are not weaknesses at all — there is great strength in recognizing the truth, the reality, of spiritual poverty; and giving mercy or being gentle or meek or making peace can all be powerfully strong things, not at all like being a doormat.
The one about persecution bringing blessing is a little problematic, because some religious and other groups have taken persecution as a sign of God’s favor when we might consider them wrong to do so. One must have additional criteria for judging a thing than just whether or not it encounters persecution. If you do feel you have good reason that your cause is just and good and holy, though, it can be a source of comfort and strength to know that the just and good and holy have always faced opposition, and that opposition does not always mean that one is in the wrong.
My favorite of the Beatitudes is in the middle:
Blessed are those who hunger and thirst for righteousness, for they shall be satisfied.
It’s the one that most resonates with me. I have a nearly pathological fear of being wrong and sinfully so. I deeply desire to be good and just and holy and right and fair and faithful and get EVERYTHING right and always do the right thing and even feel the right way and think the right things. It is a great comfort to know that God sees this hunger and thirst, and the underlying fears, and the past experiences of failure and shame, and that he promises to satisfy me with the righteousness I so desire.