The Greek word used by Jesus in his Sermon on the Mount that translates to "blessed" as in "blessed are the poor..." is not entirely accurate.
As discussed on The Bible Project podcast in the episode, "What does Blessed Mean?", there are two words in the Bible that we translate as blessed. The Hebrew word "Ashra" means "fortunate" and "Baruch" means "blessed by God."
Jesus is using the word "Ashra" in his Sermon on the Mount when typically we translate it as blessed. The way we see the word blessed leaves us thinking that God will bless those who are poor in spirit and so on. However, that is not entirely what Jesus is saying.
Another way to look at "Ashra" is "the good life" which comes from someone looking at another person's life and saying, "Oh that's the good life." This is usually said when someone is wealthy, surrounded by good people, has a good home, etc. "Ashra" or "the good life" comes from "Baruch" or "blessings from God" because the blessings come from God that eventually lead to the good life.
Instead of how we understand the Sermon on the Mount to say "God blesses those who are poor in spirit," Jesus is really saying, "Those who are poor in spirit live the good life." This is a paradox. How can someone poor, downtrodden, and deep in depression live the good life? Well, this is what Jesus's story is all about: subverting expectations.
Jesus created a group of disciples who were practically the worst kind of people at that time, the most poor in spirit kind of people, and used them to build his mission and proclaim his message. Imagine having such an important task. Those disciples lived the good life because God used them to accomplish great things. God was with them.
Jesus subverted expectations by saying that "Ashra" or "the good life" is not defined by having "good" things or being in a fortunate position. It is defined by His love and His will. If you submit to God's loving will, you too can live the good life.